Di and I haven’t really been debauched for a while. Then I called the owners of the club we used to frequent. Turns out, this solid swinging couple was divorcing. WHAT?!?!?! We were shocked. So, the wife fell off the face of the earth. The husband, Jim, is in the service business and sometimes we need his services (not the nasty kind, come on people – not yet at least).
I talked to him for a bit seeing that he was ok with his divorce. He seems to be down a little, but no worse for wear. He has family and friends to get him through. Well, being the second guy Di fucked outside our relationship, I know she liked the feeling of his cock in her pussy. One time while he was giving it to her and I was doing his wife, Di yells out, “Don’t stop fucking me!!! I’m cumming!!” That was the first guy that made her cum other than me….
I ask if he’s still friends with the couple Bill and Sue. They BOTH fucked Di one night. Sue is very awesome. She’d always bring her strap-on, and she got into Di one night. ANOTHER fabulous time. He says yeah, he is still friends with them. I suggest we should hang out with Bill. He’s all for it. Who wouldn’t be? If you know my Diane, she is a fantasy any guy would love to borrow.
Mentioning it to Di, she’s down. We make a plan for Saturday a couple weeks away. As we are going, we’re planning to just hang out in the Jacuzzi, nothing really big, because its been a couple years since we’ve swung and it is like we are starting all over. We knock. Sue answers the door naked with only her strap-on on. Not unusual to see her in this state, swinging that thing around, making a scene. But, having not seen them in a couple years, we start giggling. She laughs and says, “Too forward? Here, I’ll take it off and save it for later… Come on in, you two sexy beasts.” We go in, strip our clothes and Di heads to the Jacuzzi while I pour us some wine.
After sharing some stories and wine in the Jacuzzi, I say I need to pee. Coming back to the Jacuzzi, I see Di sucking on Bill’s cock while Sue is sucking Jim’s dick. May as well get some more wine and enjoy the view, right? So, I do. We’re all hard and horny. I love watching my little minx please cocks. And I love watching her receive the pleasure, too. Sue stops everything and says us three guys need to go sit on the couch. We dry off and sit. Then, Di comes over and starts stroking me with her left hand, and Bill with her right. Jim is saved for her mouth. She’s busy with both hands stroking cock and sucking another, God I love this woman. Just then, Sue straps on her dildo and starts fucking Di doggie. as Di switches the cock in her mouth to enjoy us all, its heaven. She’s loving it; we’re loving it; Sue’s loving it.
Sue says, “She’s ready for you.” to Bill and Jim and pulls out and grabs me by the dick and leads me to the master bedroom. Di follows closely leading the two others by their dicks. She has Bill lay down and sucks his cock some more while Jim puts a condom on and starts fucking her doggie. Meanwhile, I’m condomed up and fucking Sue doggie while the two girls kiss and suck bill’s dick. Bill and Jim switch spots and Sue let’s me take her ass. Di says she’d love to be airtight, but the guys are all too big for her tight little ass. Oh fuck, Sue says hold on and comes back with her thin dildo strapped on! “Ok, Babe. Now you’ll be airtight!” Di, looses it a little. You can see she’s on fire. I back out for the mess and let her mount Bill. She lays all the way down on him and his wife lubes up my beauty and slowly slips in her ass. After an adjustment period, Di leans up a little to take Jim in her mouth. Just before she does, she starts quivering and says oh god, fuck me! Fuck the shit out of me. Then, she starts giving Jim a real deep sucking and the husband and wife team rhythm her hard and deep.
I can’t touch my cock, because the scene is so hot I’m going to cum. Bill doesn’t last long and cums. Di hasn’t had enough, and she asks Jim to lay down, mounts him and tells ME to fuck her ass. First time for a real DP. And She and I and Sue and Jim and Bill all know we aren’t going to last very long. I’m out in about 2 “Oh, Fuck Hugh, that’s so good, I’m cumming” screams from her, which is about 10 thrusts. Haha.
My bisexual tendencies were known by Jennifer before we married. My male encounters had been at school and later at an all male college. There weren’t hundreds of guys but the sex had been quite intense and probably unusual for a guy like me I had actually had active and passive penetrative sex with a room mate I had really fallen for. He moved on and so did I and when I met Jenny, she was my first proper girlfriend. She had the shiniest brown hair I had ever seen and her piercing blue eyes captivated me. She was a good six inches shorter than my six feet but had a great body and pert 38 inch bust which she displayed to good use in reeling me in.
She kept me from sex for over three months. My female contacts had been limited and at 18 I had only had sex with three girls. All of them had been one night stands so my confidence with someone I really liked was somewhat limited. When the night came, I drank too much and she took complete control, dominating the whole sex session and sat astride me for penetration. Thankfully I had no erection problems as I thought I might. This was almost definitely helped by her dominant role.
It was that night I told her about my sexual history. The drink set it off and relief at achieving a decent orgasm for both of us made me braver than normal. Surprisingly she took it in her stride and asked me some intimate details about what I had done and how much I had enjoyed it. She told me about her sexcapades including one threesome with another girl and her boyfriend so I felt we both had a slightly kinky past.
At 22, we were both in a shared rented flat we called home. She was still at university and I had just taken up a junior apprenticeship with an accountancy firm. We hadn’t married and we were still shagging like rabbits. When we were out on the town she would tease me when a cute guy went past.
“Fancy his cock in you then Max?”
Thank goodness she had stopped calling me “Maximillion.”
“I think he’s more you than me,” I would joke back,
She knew I still had a penchant for college guys mainly, I suppose, because I had lost my virginity to a college guy. I knew she loved fresh meat too but it was all talk and banter. I loved the honesty in our relationship though I hadn’t told her that I was beginning to get a very strong urge to suck cock and only my love for her stopped me for searching for it.
Jenny came in from university one evening and said, “Apparently you’re a poof.”
“Sorry?” I spluttered from within my mug of tea.
“There’s this little stud at university who told me today that you had been shagged up the bum by his gay brother. He obviously has the hots for me and thought that by dropping this bombshell it would have me in tears and hugging him for comfort. His name’s Leo and his brother is Matt. He was quite upset when I told him you had enjoyed it and particularly his brother’s big cock!”
“I didn’t say that,” I said.
“I know but it was enough to have him walking off scratching his head.”
“What was he like?” I asked.
“Bloody cute! He looked more 16 than 18 and was only my height. He was very slim and very boyish. He also looked very randy!!”
“Jenny, how could you?”
“Well you were fucked by his gay brother,” she responded with a sly smile. “The little runt needs taught he shouldn’t go maligning people’s lives though.”
The subject was dropped and she told me a few days later that apart from the odd shy smile, he had kept his distance. Things changed about two weeks after that when she told me he had made conversation with her again and asked if it hadn’t bothered her that her boyfriend “took it up the arse.”
She told me that she had said it was quite the opposite and she would love to see it happen and would even love to be involved, however, we were loyal to each other.
“Did you actually mean that? I asked,
“I think I do,” she said, “but it’s for selfish reasons, I quite fancy the little runt and I’m sure he’d be crap sex so quite right for dominating. Then I could threaten him about his sex life. Obviously his brother would be useless if he’s 100% gay.”
“Jenny, are you suggesting we have sex with someone else?” I asked, my heart pounding and cock swiftly rising.
She leaned across and squeezed my crotch. “I think you would quite like that, wouldn’t you?”
Something I had always seen in Jenny but had never really acknowledged before was now very apparent. She liked to be in control and there was a slut inside her waiting to get out. As soon as she said she wanted sex with someone else with me there, I also realised something in me. I wanted it to happen as it allowed me to get my hands on a guy without jeopardising our relationship. My cock was brick hard.
“Come here you,” she said grabbing me by the scruff of my shirt and dragging me to the bedroom.
We fucked like we had never before. I lay on the bed, my cock standing skyward as Jenny lowered her dripping wet cunt on to me while facing me. She then rode me, her head thrown back and fucked me until I shot my wad inside her.
“Leo was panting after me again today,” she said when she came home. “I told him you were twice the man he was and he said he would like to prove me wrong. Once I tucked his panting tongue back in his mouth I told him he could only do it if you were there to watch.”
“Fuck, what did he say?” I asked my eyes like big circles.
“Naw, if I’m going to shag you I’ll do it in my time.”
“Never mind,” I said.
“What do you mean?” she said. “That little runt is so horny for me I’m going to lead him up a path he can’t get back from.”
It took another couple of weeks before she came in and told me he would do it provided I sat in a chair and let him get on with it.
“Not keen,” I said. “Either I fuck you too, or better still I get to fuck him.”
“Don’t worry, I have a plan,” she said.
On the Friday night in question she told me the plan would be that she was going to meet him in the pub on her own. Before I could protest she went on to say she was going to get him drunk, tease the prick off him the offer him a little Viagra tablet on the basis that the drink might let him down.
“He’ll never go for it,” I said.
“I don’t fail once I’m on a roll,” she said and off she went looking as sexy as hell.
I was glad they weren’t meeting in a Uni bar, I showered and, for some reason cleaned my back end really well, probably in the hope of getting the double whammy of two brothers, even if one was straight. I had a couple of drinks too, just to relax me and it was after 10pm before the telephone went. They were on their way.
I was wearing a white t-shirt, and a jock strap under my track suit bottoms. I heard her key in the lock and the two voices. Jenny entered first followed by the most stunning creature I had ever seen. He looked like an angel from the wrong side of the tracks. Stunning blue eyes, dirty blonde hair, a short athletic body and wearing a grey t-shirt and slightly loose fitting jeans but with a cute little point where I assumed his cock was being held by his underwear. I wanted him!
“Leo, this is Max, Max, this is Leo.”
The hand came out and I realised the lad was slightly pissed.
“Want another beer to relax you?” said Jenny.
“OK,” he said sheepishly, avoiding my eyes.
I took the bull by the horns. “I’m so looking forwards to seeing my Jenny being fucked by someone else. It turns me on.”
“She’s a stunner,” he said, “and if that’s what it takes, then so be it.”
Jenny looked stunning when she came back in with the beers. Her top was almost transparent and her nipples noticeable underneath. Her short ivory skirt rode up as she sat down and he could probably see her panties when he sat opposite her. I saw him adjust his cock.
“The Viagra works doesn’t it?” she asked.
“Too fuckin’ true. Not sure I needed it though,” he replied.
“You will for what I have planned,” she said, slipping off her top to face him topless.
“You lucky bastard,” he said.
It took a moment to realise he was addressing me.
He put the can down and crawled over to Jenny on the couch, crawling up between her legs to hold her right breast until her nipple stuck out and then he licked it before taking it in his mouth. He moved to the left breast and then stretched up to kiss Jenny. My cock was at full mast. Seven inches of stiff bisexual cock straining to get some action and not sure if it was going to.
Jenny stood and unclipped her skirt letting it drop. She was naked, the briefs having been discarded.
“Fuck,” he said as he took in her beauty.
Still on his knees, her vagina, the hair neatly trimmed to a small stripe, was aimed right at his mouth. He looked up at her and she stepped slightly closer. His tongue slowly slid out and gently licked the closed slit leading to her vagina. I could see the petal-like folds of her clitoris sticking out from the slit as he licked round it.
Jenny sat back down and opened her legs wide. The red gash opened like a flower in bloom and little Leo dived in like a hungry animal, slurping and licking. My hand was inside my pants, stroking my cock. I didn’t want to do anything to scare him at this stage so wanted to wait until the whole show began.
His groans as he lapped and slurped between Jenny’s legs was really getting me going and I hoped he wasn’t so randy he shot off prematurely.
Jenny stood and said, “Stand up!”
Leo looked like a little boy alongside her as he stood up obediently. She pulled off his t-shirt and a slim but well-defined body came into view. A few wispy blonde hairs appeared on his chest and a darker trail came up from his pubic area. He tried to kiss her but she stood back and unclipped his jeans. They fell to the floor and he stood in a multicoloured pair of briefs with a bright blue band, his erection pushing a point at the front. As he stepped out of them, she whipped his briefs down and his cock sprung up as if a recoiling spring, slapping against his belly. He had small tight balls with dark blonde hair sprouting from them and a 5 inch cock with foreskin covering its head. It looked hard enough to hammer nails. He was better looking than his brother and the thought that, just maybe, I might score him too, had my cock stiff as fuck.
“Max is going to fuck me while you watch Leo,” said Jenny.
That was new to me but, once he looked at me, as though suddenly remembering I was there, he stood back slightly and I stripped quickly. I saw him look at my cock in surprise. It’s not massive but was a heck of a lot bigger than his.
“Stay close Leo, I want you to watch and to stroke me,” said Jenny.
He slid to one side, still on his knees and I lay behind Jenny, entering her from the rear so that my cock’s entry was clear as day to Leo. I slid it in her sloppy wet cunt and started to fuck. Leo stroked his cock and watched. If you have never been watched by a horny guy while fucking, you should try it. I held Jenny’s tits as my 7 inches slid fully out and back in again. I made sure the tip rubbed against her little nub as I pushed in and she rewarded me with gasps of pleasure.
“Oh Leo, finger me while Max fucks me please,” groaned Jenny.
He was apprehensive but tried to push his finger against her clitoris while I fucked. Of course it was impossible for my cock not to rub against his finger. After initially recoiling when he came in contact with me, he tentatively pushed his finger back, letting it slid inside her along with my cock. His little digit was getting me going as well as Jenny. She encouraged him and soon he was actively rubbing her and, by default me as well. I slid back and my cock plopped out straight on to Leo’s hand and again he jumped.
“Push Max back in for me darling,” said Jenny in a matter of fact way. “Pretend it’s a dildo.”
He gripped me with just two fingers and aimed my cock as I slid back into her and then, as I was behind her, he slid in front of her and started to kiss her tits. His cock was pressing against her cunt and my cock and she took her hand and tried to ease it into her alongside mine. There was limited success when I pulled half out and let his head get in. We were both half inside her and the feeling of my cock rubbing against his and rubbing against her cunt walls almost got me exploding.
“I gotta stop,” gasped Leo, “or I’ll cum.”
“Great feeling isn’t it,” said Jenny.
He quietly nodded.
“Fuck me,” she said to him while sliding off my cock and crawling into the doggy position.
He didn’t need telling twice and was on her back and inside her in a second. His fucking was frantic stopping every few minutes when he almost reached orgasm. I put my hand between his legs from the rear and handled his balls while he fucked, commenting on how exciting it was to feel someone fucking Jenny. He seemed to believe that and let me continue. I explored his balls, the length of his cock and even managed to brush my finger against his little arsehole bringing a shiver to him that seemed to be delight.
He stopped once more as he was near to flooding her with cum.
“Is this good, or what?” she asked.
“Awesome,” was the reply.
“Is my hole tight enough for you?” asked Jenny.
“Yes, why?” was his response.
“Cos I want to see you fuck my Max in the arse,” she said.
He spluttered,” I can’t do that, I’m not gay!”
“Neither is Max but it would so turn me on and you will not believe how tight the sensation is. You can do mine afterwards.”
He looked at me and I grabbed a tube of lube, squirting it on to my finger and started to lube my hole. I said nothing as I took his cock and stretched a condom over it, lubing it.
I simply crawled into the doggy style, saying nothing at all.
Jenny gripped his cock and led him to my arse. He entered me almost as violently as he had entered Jenny. His inexperience showed but soon his little hard dick was in me to the hilt and he was hammering my hole.
“Oh my God, that’s so tight,” he groaned. “Oh fuck, oh fuck,” he continued and then tensed, the force of his ejaculation actually vibrating as it coursed up his cock into the teat of the condom.
My own cock erupted on its own spraying jets of cum over poor Jenny’s tits as she lay on the bed.
“Please don’t tell my brother,” he said afterwards.
“I won’t,” I said, “as long as you fuck Jenny again before you go.”
It wasn’t too difficult to get him to agree and he did.
Leo became obsessed with our threesomes and gradually became more obedient. He wouldn’t let me fuck him but on the next visit, I was able to suck him. He enjoyed my technique and was soon thrusting into my mouth. On that visit, after we both fucked Jenny and I was again able to take his cock up me, he shared his cum with both of us, firing over our waiting mouths.
“Is your brother still an active gay?” she asked Leo.
“Yeh, he came back home after being in London for a couple of years but the job went pear-shaped so he’s back looking for work.”
“You ever wonder what he would be like to fuck?” she asked him.
“He’s my brother!” he said quickly.
“Max, what was Matt like in bed?” said Jenny, that evil little glint in her eye I knew so well.
“He’s quite big, I think over 7 inches and also thick so it was quite painful when he stuck it in my hole but he fucks well and also was a great cock sucker.”
Leo was quiet. “I think he had a girlfriend in London,” he said.
“Oh so he could be a bit bisexual,” said Jenny.
“I suppose so,” said Leo, not sure where this was heading. That made two of us.
“I might get Max here to give him a ring for old time’s sake and invite him for a drink.”
“Are you gonna screw with my brother too?” he asked his bottom lip suggesting he was jealous.
“Are you upset because we’re going to have him and you don’t want us to have someone else or are you upset because you want to have him?” she asked, smiling.
He went quiet.
“Have you honestly never looked at him and thought, I wonder?”
“Well I did wonder what he looked like when he was having Max here.”
“Why don’t you tell him you’re meeting us and we would love to meet for a drink, all four of us, and see what he says?”
This conversation went on for an hour before he agreed. He said he wouldn’t confess that he had had sex with us, nor to his fucking me up the arse. I figured his brother was a smart enough guy to realise something was going on. Whether this would develop into anything, I had no idea.
When I answered my phone, three days later the voice was instantly remembered. “Max you randy old sod, how are you?”
“Hi Matt, I’m great and all the better from hearing you. God how long is it?”
“Three years. I think the last time we met was……oh never mind.”
I remembered. He fucked me and I fucked him in a bed and breakfast room we had rented. I knew he was moving in a month’s time and wanted a really good session. We thought we had a few more sessions to go but he actually had to leave quite quickly and, apart from diminishing telephone contact, that fuck session was our last.
“How did your brother know about us?” I asked.
“He knew at the time but as he was too young to go to university then so it didn’t matter. I assume he told you he knew? I hope he didn’t splurt anything to your girlfriend.”
“Actually he did but thankfully she knew.”
“That little cunt I’ll kill him!”
“No need he just fancied his chances with her and I don’t blame him, she is a stunner.”
“Well I’m glad he didn’t get anywhere with it.”
There was silence.
“He didn’t get anywhere with it, did he?”
I let the question hang.
“Let’s say he got more than he expected.”
“Leo, straight horny little Leo did a…….threesome??”
I said nothing.
“He didn’t……you know….do anything with you?”
“He was horny,” I said.
“Was he as good as me?”
“I can’t remember. Perhaps you might wish to refresh my memory sometime.”
The conversation went on and we decided to meet Matt for a drink. Leo wasn’t mentioned but I called him and suggested he come along for a drink. He was reluctant but I have a feeling he was concerned and jealous that his brother might get something and he wanted to be there to block it by being a wallflower. He obviously didn’t know Jenny that well!
The night, when it came, raced along at breakneck speed and the drink was consumed at the same pace. Jenny can hold her own with the best. I was catching up with Matt and Leo was sitting very close to Jenny, his hand occasionally straying on to her thigh when he laughed or wanted to make a point.
“Did he fuck you,” said Matt quietly.
“Yes,” I replied.
“Well I fucking never,” he said. “After the stick I got from him when he found out I was gay, for him to go and screw one of my exes is something else.”
“Let’s polish off some wine back at ours,” announced Jenny. “None of us are working in the morning and I’m in the mood for a laugh.”
She rose and walked out assuming the answer would be positive and we all followed meekly, looking at her arse as she swayed down the street with Leo running behind to catch up.
Back at the flat, she kicked off her shoes and shucked her bra leaving only a lightweight top covering her breasts her nipples clearly showing. I saw Matt looking and Leo didn’t miss them either.
“What’s she up to Max?” Matt asked me.
“I’m not really sure but I can tell you she’s horny. How she turns this odd situation into anything is anyone’s guess.”
Leo was oblivious to both of us. He was laughing at everything Jenny said, waiting on her hand and foot and Jenny, in return was kissing him lightly on the lips while he rested his hand on her thigh while he sat between her legs on the floor. As I went to get a few more beers, Matt followed me to the kitchen and when I turned from the fridge, he kissed me.
“I just wanted to remember what it was like,” he said. “It’s funny that the guy who loved getting fucked turned out to be the one with the girlfriend.”
I am not a cliché aficionado but one stands out in my mind, “do not wish for something unless you are prepared for it to come true.” Before talking about why this cliché stands out, I will introduce myself and provide some background. Jennifer is my full name but many people call me Jenny. Currently, I am 40 years old, l I do free lance advertising and living in a small town of Poldick, South Dakota. The surrounding area has more farm animals then people and still has buildings built by pioneers, who settled this town. My feeling the town’s link to pioneers gives a general impression people from this area are conservative, religious, and innovative. In some ways, if feel that impression describes me.
In retrospect, a lot of my life, including my decisions, is somehow associated with growing up in a rural town not too far Poldick. It is fair to say my parents were conservative in every aspect. Growing-up watching television was limited, due to my parents believing television programs having too sex or promoting a progressive liberal agenda. If I was not doing homework or outside with my friends then I was at church doing something in order to keep my parents happy. This led me to develop a rich fantasy life due to the isolation living in a rural area but at the same time being afraid to experience something new. The fear of adventure and always wanting to do the right thing led me to live a very insulated life.
During my teen-age years, growing up in a religiously conservative home meant I did not date until I was a senior in high school and it was not until prom that I had my first kiss. It was not until I moved out of my parent’s home studying art at university that my life began to change. During my junior year at university, I met my husband Dan whom was in the same Introduction to Sociology class with me. His intellect, English accent, and having experiences different from mine initially attracted me to him. Unlike me, Dan was not a virgin when we met. This does not mean I was frigid. My sexual interests were quite alive, I willing to explore but I kept having sex as a fantasy. One example where I can give of my sexual interest being alive, while at university if I had a few moments alone I would take my pants and panties off to play with myself while fantasising about being the object of desire. Another example my roommate Penny and I would go out partying together then come back to our dorm room exploring each other’s body. Nothing materialized between Penny and me. Then there was Robert whom I dated for about six months before meeting my husband Dan. Robert was a lot like me in many ways idealistic and had his views shaped by living in a religiously conservative home. Such backgrounds made our relationship difficult because we had limited experiences and the experience we had made our conservative background limited our physical involvement with each other. This meant my experience with him was limited to petting, nothing more. It would be fair to say that prior to meeting Dan I led a cloistered life with many of my ideas about sex based on fantasy or religiously conservative ideas.
As I started knowing Dan, I learned about his sexual experiences including a threesome with two women and a drunken bj with his roommate, though he did not go into much detail about it. His experience, I feel, made him more willing to take a risk in our relationship. At first, this lead to some conflict due to our differing viewpoints but as we learned more about each other, we learned out to work through it. After graduation, we were married starting to live the American dream, a house, careers, and children. If you looked at us after nearly 20 years of marriage, we would appear as any other married couple. However, if I just lived the American Dream, there would not be much of a story to tell and the story would end here.
After getting married, our lives were nothing spectacular. In the beginning of our marriage, sex was predictable and I was reluctant to try anything new. Dan is always the one suggesting new things and pushing new things to try. Most of the time I will reject his ideas but as time passed, I tried some of his suggestions, such as sharing a fantasy during fore play. A common fantasy was having sex with another man with Dan participating or arranging something then telling Dan about the details. This fantasy came from occasionally watching threesome porn together and our discussions about trying it. There is a few times when we started to look for a third person to join us but I would say ‘no’ due to my fear about the risk. Another common activity for Dan and I, tying Dan down with some of his older ties and then doing what I wanted with him. Tying Dan down gave me a sense of power, a sense of control, and allowed me to break out of the shell that defines much of my life before Dan. Dan’s patience with me along my willingness to explore, in some ways allowed me to be more sexually competent. Nonetheless, in my private moments, I still like to play with myself fantasizing being the object of desire for another man while Robert watched.
With that said, if you were to ask me before 4 May 2011 if I had any regrets, I would confidentially say there was one, not going all of the way with Robert. However, that was going to change. The week begins like any week for us, since were on vacation and staying home. Since we were staying home we kept our morning routine of discussing world events. Then on May 4th,, the day before an election in the UK, Dan and I decided to bet on the outcome of the outcome of the Alternative Vote (AV) referendum in the UK, Since Dan is originally from the UK and politics is something he enjoys. He felt that the UK would not approve AV but I felt the idea was a good idea because it provides a fairer voting system. This lead to a lively debate at the breakfast table and we decided to solve our difference with a wager on the outcome.
Unlike previous wagers, this one was different and I am not sure why we moved our wagers from non-sexual to sexual. It could be as a couple we were heading in this direction or it was due to both of us being on vacation. My wager was an unassuming one, being able to tie Dan down using restraints and dominate him. Dan knew about my relationship with Robert, the attraction I had for him, but never said anything about it until now. His bet was unexpected if he won I would find Robert, sleep with him, and I would arrange it. Since our bets are more innocent than this, I told Dan, “I need time to think about it.”
“Okay, I will give until this evening but unless you tell me otherwise, I am going to assume my wager is acceptable.”
I felt he was joking about his wager because as a couple we knew where the implied limits existed and I know he would not expect to do something that I was not comfortable doing. Nonetheless, it did get me thinking and wondering what it would be like to be with Robert and the thought started to get me aroused. A few explicit images, of Robert fucking me, ran through my head before Dan said, “I am off to do the weekly shop.” That gave me at least 30 – 45 minutes where I could go upstairs and play with myself thinking about how much I might enjoy it. Once I got out my dildo, it made me think more about fucking Robert. The thought of him fucking me now made me quite wet and I could feel my pussy yearning for Robert’s rock hard shaft inside of me. A few moments later, I could feel my pussy wall taking command of the dildo by grasping it as I shoved it in faster, and at that point, I knew I would agree to the wager.
After thinking about Dan’s idea, it left me with a quandary. If it happens, it will mean our relationship will change but at the same time, I knew I wanted to fuck Robert. I took some time to think about what it would mean. After Dan came home, having some time to think thinking and considering it, I decided I was going to tell Dan my decision. I nervously approached him, “Are you sure of your wager?”
“I am not sure I understand what you are saying?”
“We do this as something fun between us and we never defined what was out of bounds for a wager.”
“I know,” Dan said, looking down and away from me, while taking a pause before continuing. “We have never formally discussed and I have always assumed that this was for a bit of a laugh. Fun you know, never forcing the other to go through with the wager if they were uncomfortable with it.”
“I agree. I am afraid it could damage what we have and I am afraid that I might enjoy it too much.”
“Enjoy it too much, a bird like you?” Dan begins to laugh. “You have always been a bit conservative. I think you will want to do it once just to see what it would be like and then the novelty will wear off.”
At that point, I felt as though 1,000 people were staring at me that was holding onto every word I said because we never had this type of discussion before and I felt Dan knew me more than I knew myself. There was a long silence and feeling as though blood was facing to my face, Dan broke the silence by saying, ” Do not worry, yet, the outcome is not known and I have some boundaries that need to be agreed before it goes a head for me.” Dan took a long pause and I thought he was done speaking until he said, “I always felt there was something unresolved between Robert and yourself. Maybe because of your backgrounds, growing up in the country, or I don’t know.”
Shocked by the fact I am still open to idea; I prodded by asking what were the boundaries. “They would be it is a one-time thing, I knew when it was going to happen, and no communicating with him after it happened.” At this point, I felt a flurry of feelings range from sheer excitement to being utterly upset. Feeling upset came from the uncertainty that it brought and the fact I have not fully resolved the conflicting beliefs I have about the wager. Whereas the excitement came from the fact I might be able to arrange for Robert to fuck me. Now, I could feel my nipples getting hard and beginning to feel moist between my legs. Dan then said looking at my chest, “I can see you like my response,” with a smile on his face.
“So you are happy, if I try to find him online and contact him?”
“Yes as long as you are transparent about what you are doing, you keep me updated, and we periodically talk about it.”
After the conversation, I went back upstairs and I was feeling confused. At part of me was wondering if Dan suggested this because he knew I did not keep in contact with any ex boyfriend and was confident I would not find Robert. Moreover, there was some doubt in my mind if I could actually go through with this if I found Robert. This left me wondering if Dan suggested this wager since it was more likely a fantasy than reality.
I decided to go downstairs to speak with Dan again and to confirm that he is comfortable with the idea. Speaking with him he says,”I know you feel this wage is a bit out of character for me; I know you still have a sexual interest in Robert and fucking him might do you some good. I am not going to push you into something you do not want to do.” Silence fell for a minute and Dan continued, “I love you and this needs to be your choice, if you loose. If you want I will pick something else that is less threatening.”
“No, I am alright with that. I needed to be sure in my mind that this was not a joke.” With that statement, I left him and went back up stairs to begin my search. As I began my search by looking at various social media websites, it suddenly dawned on me, if I found him what would I say? I thought about being causal by saying, “It is a long time since we spoke,” and then try working up to my idea. However, I thought that would take a while and I was trying to move things faster. This left me with a dilemma in determining the best way to solve this problem and after contemplating the idea, I came up with a solution. The solution involved me being the seducer by pretending to be someone else and once we meet surprising him. Being the one who is pursing him got me quite wet and feeling flushed, in a way it felt like a rush. Sliding my hands down my pants I could feel how wet I am becoming and spent a few moments imaging what I would be doing with Robert.
I looked up at the clock in our office said 10:43 and most of the morning has now passed. If I was going to find Robert, I needed not to let my mind wonder. After a bit of searching, I found him on a social networking site and he lived only 50 miles from us. A bit nervous, I tried to hide my identity when I made contact with him by sending him a message. Once I made contact I felt I took it as far as I could and hoped that he would respond. Instead of nervously waiting for a reply at my computer, I decided I would do a few errands then check back. It was about 14:23 when I checked my computer to see if I had a response and to my surprise, I did. Not sure, what my next step should be and thought, “How do I move this forward without appearing too anxious?” My heart was beginning to race and my palms became sweaty. Soon I was considering other questions in my mind, “Do I need to tell him that I am married? What is the proper etiquette?” After taking a brief pause allowing myself to calm down, I decided a video chat would be the best way to handle this and suggested it to him.
It took about 5 minutes before we could see each other and I was nervous thinking to myself, “Will he recognize me?” If he did recognize me from all of these years then I will not try to hide it admit but if not, then I will play along.
At first he said, “Hello,” with a lot of tension in his voice and to me it indicate he was nervous.
I then responded with a confident and cheery, “Hello.” There was a long pause felling as though it was 5 minutes but actually, it was no more than 30 seconds. Capitalizing on his nervousness, I could feel a sense of power in trying to achieve my conquest and being the one who is doing the pursing. Knowing I could capitalize on this moment my decision was to play an innocent but confident woman. This meant for me trying to flirt with him and then letting the conversation happen.
“You look like someone I knew a few years back.”
“Really?” His statement told me he was not sure who I am.
“Yeah, I was attracted to her but we were young… Nothing developed and we soon went our own ways.”
“What do you think you would do if you saw her again?”
Robert paused a few moments, a smile broke across his face and his voice had a child like innocence to it. The innocent sound to his voice told me, this is something he does not readily share with someone and he is being genuine in his reply, “We were young and inexperienced. If I did meet her again I guess, I would like to go all of the way with her.”
Coyly I asked, “Have you spoken with her since then?”
“Are you sure?”
“As far as I know, I haven’t.”
“What if I told you, that you are speaking with her now?”
“Really!” His eyes were getting wide and I could see Robert was trying not to look too excited.
“Yes, I am married. However, my husband knows I am searching for you and there is more.” At that point, I could see some of his excitement leave his face and a look of puzzlement enter. The look I would say is similar to someone playing a slot machine that is expecting to win big only to discover they won a few dollars. Noting the change in his look I continued by saying, “I can see you look puzzled and I will try to clear up some of the confusion. My husband and I like to bet and he bet, if he wins, then he wanted me to have sex with you? We are now waiting for the result since bet is based on an election.”
“How you feel about that?”
Pausing for a few seconds to consider, my next words since what I say will determine if this goes forward. “At first, I went through a lot of different feelings but I soon discovered how much I wanted to fuck you.”
“Okay, let me back-up a bit so you understand what is being considered.” As our talk continued, I could see him again relaxing and I could tell from his expression that his interest remains. “What were are considering is either a threesome with my husband or letting me be a lone with you then telling him about the experience. So this is an one time chance to make it happen.”
“The idea sound quite tempting… A lot has changed since we were younger.” A long pause, “I do not know how to say this.” I can see on his face is struggling to decide if he is going to say something. The look on his face reminded me a lot of a young child that broke something and is unsure if they should admit to it, “Well, here it goes… If we did go through with this, I would prefer the threesome option with your husband there.”
“Okay, um, is there any particular reason?”
“After our relationship ended… I had a few relationships with both men and women. So, I prefer both… If you know what I mean?”
“You know I come from a fairly conservative background. Even though I have changed a lot over the years, I do not know if I am comfortable with that.” My response to Robert was due to the shock of hearing he is bisexual. At this moment, in the back of my mind was, “How is Dan going to react? Will this force Dan to change his mind?” The idea of being with Robert sill arouses me and I want to this to happen. Before making any decision regarding speaking with Dan or telling Dan to consider another option, I decide I will ask a few questions. “When you say that you have been with both men and women are you now playing for the other team?”
“I am not sure that I understand?”
“I guess, what I am asking is do you only prefer men… Now?”
“No, I like women too but if the opportunity to be with a heterosexual couple came up then I would take it, if you know what I mean?”
“Okay, so if I understand you correctly, if there was a threesome with Dan and myself you would want to be able to interact with both of us?”
“So, when I talk with Dan what are you proposing that you would want to do with him?”
“I am not looking for anal with him. Instead, I am open to touching, oral, and mutual masturbation. If he is not open that then I am willing to have a completely straight threesome with him”
“I cannot speak for Dan and need to get his feelings on this. Will you be online later?”
“We are on vacation and he is home at the moment. Once we know the outcome of the vote and I have a chance to speak with him, I will let you know what he has to say.”
“Bye for now.” After signing off I thought to myself, “this whole bet is beginning to get complicated and almost unmanageable.” I went downstairs seeing him watching television, approaching him I say, “You realize, I was speaking to Robert online while upstairs?”
“Really, what did the two of you talk about?” By his tone, I knew Dan was interest was more in me and I know my current ambivalent feelings about this will show through my conversation with him.
“Catching up on old times and what we have been doing since school.”
“Anything … else?”
“Well, we did talk about our bet.”
“He is definitely interested, but um… How do I say this,” pausing before I continue. “Dan is bisexual and he wants to have a threesome.”
“You are fucking kidding me!”
“No I am not.”
“I don’t do that. I am not a canary!”
“I know you are not and I told him that. Robert said, he was looking for some touching, maybe some mutual masturbation, and maybe him giving you a bj or you giving him a bj. I told him I would have to speak to you about it.”
“Is he only into blokes or birds too? I am not going to do another bloke in front of you!”
“No, he is into both and is still attracted to me. He said he would be alright with it if there was no interacting between the two of you I would expect that he will interact with me too.”
“Okay let us see the outcome of the vote and if I am the winner, then I can talk with Geoff about this since he tells me a bit his threesome adventures.
Election Day was 5 May 2011 with publication of AV results on the evening of 6 May 2011, we followed the returns online and AV was soundly defeated. After it became apparent that AV was defeated, Dan said, “Why don’t you contact Robert to let him know the outcome? I will contact Geoff to get some input but do not agree to any meeting, yet”
“I can, but don’t you think it would be better for me to speak with Robert first?”
“You are not agreeing to meet him but let him know I have won the bet. Tell him you might have an answer for him in a few hours and if not, no more than a few days”
“Yes, let me know the result of the conversation.”
Dan left the room so that I could have some privacy with Robert and not have a background conversation while speaking with Geoff. I found Robert and suggested that we once again use personal messaging with video. After both of us finished logging in, I stated with a smile and jokingly said, “Dan won the bet and is looking to collect.”
“I see…” Robert had a big smile on his face and deciding to tease a bit, I remove my pink night top exposing my 34B breasts. “Very nice.”
“I thought you like… Are you going to help Dan collect his bet? Or do I need to find someone else?”
“No, I will definitely help him collect.”
“Great, he is a bit uncomfortable with the idea of having contact with you and he is talking with a friend who has had threesomes with men. I do not believe he will change his mind on it and I might know a bit later this evening, will you be contactable?”
“Yes, I will and if I am not online send a message and I will get it the next time I sign in.” Before I could tell Dan about my conversation with Robert, he left to speak with Geoff.
“When I knocked Betty answered and direct me to the basement. I have not seen the basement since you finished decorating it. You all right, mate?”
“Yes, you said you wanted to discuss something with me?”
“Here it goes, mate. I thought I would ask you since you are always telling me about your threesomes with Betty.”
“Well you see, I bet Jenny if I won we would have a threesome with her ex-boyfriend. He was a bit of a wanker at university and I do not see him as a threat. Jenny spoke to him and blimey it turns out that he is a bit camp.”
“So, he is playing for the other team? Gay?”
“Oh no, he likes birds too but I just don’t know what to think. I have a chance a threesome and being able to watch Jenny enjoy herself. If I say no then I don’t know if I will have another chance.”
“A few general points about having a threesome.”
“Okay, then tell me.”
“First point, nothing happens in a threesome unless you agree to it, which means ‘no’ means ‘no. Second point let him know you limits and the farthest you are willing to go. Third, you can have a threesome with it being straight and no male on male contact.”
“So, what you are saying is the threesome can happen without turning me into a canary?”
“Are you open to doing anal with him?”
“Okay, this defines a limit for the activity and I suspect he will understand if you do not want contact?”
“According to Jenny touching does not have to happen.”
“There is three options for you if you decide touching is fine. One is you taking a hold of his cock then helping him to enter Jenny. Second, the two of you could masturbate each other in front of Jenny. Third could be sucking him off or him sucking you.”
“I do not think I want to go that far.”
“If you want I can take off my jeans and you can have a go at feeling my cock. It will give you an idea of what it might be like”
“Won’t Betty mind?”
“No, we have an open relationship”
“Are you sure you are alright with me touching your cock? I am not sure what to do.”
“Don’t think about it, just go with what you feel and watch my body to let you know if I am enjoying it.”
“Alright… I guess. Do you want me to take your pants off or do you?”
“I will, give me a moment as I unzip my jeans and slide my underwear off. What do you think?”
“I did not think you could get hard that fast. I did not know you were that big.”
“I never told you about my fantasy of you stroking my cock.”
“Come closer, so that I can feel your cock. It feels hard but the skin is quite moist, not what I was expecting.”
“Oh, yes that feels good, faster.”
“No offense Geoff, I cannot go through with this and thank you for helping me work out what I need to do. I am going to leave, now.”
“Jennifer are you home?”
“Yes, give me a minute. I will be right down!”
“Did you speak with Geoff? What did he have to say?”
“He gave me some insight into having a threesome and I learned that I am not into male on male contact.”
“So, what are you saying then?”
“I am not sure… I think I am saying that I would like the threesome to happen but I want to watch, not participate.”
“Are you sure, that is what you want?”
“Alright, I will contact Robert and make the necessary arrangements.”
Jennifer logs on to her instant messenger. After logging into the instant messenger, Jennifer sends Robert, “Hi I am online and spoke with Dan about the bet. Let me know when you’ll be online so we can discuss further.”
With no response Jennifer is about ready to log-off when she receives an instant message from Dan, “Hi, was not sure if I would be able to chat with you.”
“I was about ready to log off.”
“Dan did some thinking and is not comfortable being with another male.”
“Oh darn, I was looking forward to meeting him.”
“You will meet him. He said he wants the threesome but wants to watch.”
“Oh really, that is super.
“It is getting late, I am getting tired, and I need to get up early. We will talk some more tomorrow and make arrangements. Bye for now.”
After signing off with Robert I thought to myself, “I am going to see if I Penny is online so, we can chat and get her opinion on this, I am going to send her a quick message to see if she responds,” Jenny thinking to herself. “Penny, I need some advice, can you chat?”
Knowing it might take Penny a few minutes Jenny waits and is about ready to sign-off when Penny responds, “Is anything wrong?”
“No, I am confused and thought you might be able to help?”
“Are you and Dan having problems?”
“No, the advice I want regards threesomes. I know you have said that Charlie and you occasionally have threesomes. Well… I have an opportunity for something like that; however, I am not sure about it.”
“What are you unsure about?”
“Long story short, you remember Robert from university. Well, Dan bet me sleeping with Robert if he won. He won but I found out Robert is bi; Dan wants to watch, not participate but I am not sure.”
“You remember our sort-of bi experience back at university? I don’t think that will change anything about Robert and I always felt Robert was attracted to you. Though I never believed he was not straight.”
“I guess what I want is Dan participating and I feel, if he is not participating then it takes away from the experience.”
“The experience is wider than Dan and you. It is about being desired by two men at the same time and them pleasing you. Even though Dan may be watching he is still there with you and enjoying seeing you enjoying yourself.”
“I know, that is why I am still considering it. In my mind, if Dan is not participating then I feel it is cheating.”
“It is not cheating, as long as both of you agree and the threesome does not go beyond what is agreed. From what I remember of Robert he did not seem to be someone that would destroy a relationship or go beyond any limits set.”
“I don’t fully agree with your definition of cheating that but I do understand what you are saying. Have you even done a threesome before where Charlie just watched?”
“Yes we have. However, I need to leave in a few minutes; I will save it for another time. Let me tell you from experience, if Dan believes you are enjoying yourself, he will be too horny to control himself and will join the two of you.”
“What you are saying I should go ahead with this and Dan might join in?”
“Great, bye for now. Bye.”
With that, Jenny signs off her computer and speaks with Dan. “Dan are you awake?”
“I have been doing a lot of thinking about what you said and I am willing to go through with it.”
“Great, make sure you let Robert know,” Dan said with a tired voice.
“Trust me, I will. I am going to email Robert”
Going back to her computer Jenny boots it up and sends Robert a quick message, “Everything is a go, contact me to make plans.”
“It is getting late,” I thought to myself and I will arrange with Robert in the morning and after leaving the computer, I went to bed.
The morning of 7 May 2011 is sunny with very little clouds and warmer than usual. I awoke at 08:00 with Dan still asleep in bed. That morning I made a light breakfast before taking my shower, and seeing if Robert replied. Logging into my account I find Robert replied, “Glad to see things are moving forward and I am available on Saturday. Let me know the details, Robert.”
After reading that message from Robert, I knew things would be moving fast and if things worked out then by the end of the day, he will be fucking me. Responding back to Robert, “Available today too. Let me know your availability.” Still being early in the morning, I did not expect Robert to respond immediately back. I decided to enjoy the quiet that existed. It was around 10:00, I could see that Robert was available. “Hi,” I sent to Robert to see if he was at his computer or away.
A few minutes later Robert responds, “Hi, so it looks as though it is a go?”
“Yes, it is. To be honest with you, I am a bit nervous and still a bit unsure.”
“Don’t worry Jenny; nothing is going to happen unless you want it to happen. I am not going to push you to do something that you are not ready to do nor will I do anything that will hurt your relationship with Dan.”
“That is good to know. Before going forward I do want to confirm what is being planned in order to prevent any confusion. It will be a one-time situation with Dan watching but I suspect if he gets horny enough he may want to participate.”
“I can live with that.”
“Also I am not sure where my comfort level lies, at the moment.”
“Again, that is fine. If you ultimately decide against it or if I perform oral on you without having sex, I can live with that.”
“What are your thoughts about meeting, tonight?”
“Since you live in a small town, I do not want to attract attention, and I am assuming you do not want to attract attention either, I was thinking meeting in Redman City, Iowa. We could each book a hotel room at the same hotel and then meet for dinner.”
“Sounds good, but it will take us a few hours to drive to Redman City. It also means I need to pack and get Dan moving. My feeling the earliest we will be there will be around 17:00.”
“If you send me your cellular number, I will text you the hotel and my room number.”
“I will bye for now.”
Trying to make it to Redman City by 17:00 meant I did not have much time to waste since it is close to 11:00, I have to get Dan moving, pack, and try to leave by 13:00. Luckily, Dan was finally moving about, though still groggy from sleeping, “Hun, I spoke to Robert online and we need to leave.”
“Watcha on about?”
“We agreed that we would meet in Redman City about 17:00, we would book a hotel room and he would book a room at the same hotel too. He is going to text me the hotel and restaurant. So there is not much time to yammer and we need to get moving.”
“Flippin’ell we need to get a move on.”
With that said about 20 minutes later Robert texted to me the hotel and restaurant, I texted back, “So far we are on schedule and should be on the road by 13:00 or shortly thereafter, see you there.” After, the text I booked a room at the hotel and I finished getting ready. It was about 12:30 when Dan & I started packing for our weekend getaway. Dan picked up my dildo that we sometimes use to simulate another cock in me and said, “Do you want to bring this with? Otherwise it might feel left out?”
“I think I will be getting enough attention tonight and I don’t think I will need it, tonight.” With that Dan walked over embracing me, kissing me on the forehand, and then said, “I love you, I think we are going to have fun tonight.” With that, we grabbed our bags and loaded the car. Once we were on the interstate heading towards Redman Cit, Iowa I texted Robert, “On our way and should be there in time.”
The next four hours in the car was quiet and I am not sure the reason. It could be that we needed the time emotionally, to prepare for the evening, or that we did not want to say something that would ruin the evening we had planned. In either case, the ride seemed longer than usual. When we arrived at our hotel, the sun was shinning and the sun felt warm on my skin. Once we were at the hotel, I texted Robert to let him know we arrived and gave Robert our room number 1023 and he texted me that he had a poolside room. I did not pay much attention to the room since the evening was going to be busy we started to get ready for supper. As we were getting ready for supper Dan said to me, “How do you want to play supper tonight?”
“I am not sure what you mean?”
“We have two options tonight, one option if everything goes alright we will come back to this room with Robert. Second option, I was thinking maybe, if you wanted you could back to Robert’s room alone?”
“I sorta like the second option but I do not know how I will feel until we are at the restaurant.”
“How about we come up with a few signals?”
“Okay, like what?”
“When we are ordering I will ask if you want a glass of wine with supper, if you want it to go forward you will say no and if you want don’t want it to go forward you will say red.”
“That is easy to remember, what about the rest of the evening?”
“After supper, if you want to go to Robert’s room you will say, I want to go. If you want a threesome, you will say lets head up or if you don’t end it then say, we need to leave early so I can prepare for my meeting on Monday.”
“That is a bit confusing, but I think I might be able to remember.”
“Main thing, you need to be subtle about what you want. Otherwise you will tip him off.”
“Gotcha.” The signals that Dan gave me helped me to let Dan know my feelings about where things are going without being obvious about it. The next two hours went by quickly and by about 19:15 we were ready to meet Robert. After closing door to our hotel room behind as the closing of the door reverberated through the floor it left me feeling both fear and anticipation. It was not until the elevator door opened and heading towards the restaurant in the hotel I began feeling horny with many thoughts running through my mind. I was wondering what it will be like to be desired by two men at the same time? Will Dan be all right with this? Will I choose the threesome or choose to be alone with Dan? Dan and I arrived before Robert. Luckily, this gave us a few minutes to talk before Robert arrived.
“Regardless of what happens tonight, I want you know that I still love you, Jen.”
“Remember, to go through with this or not, the final decision lies with you. Unless I get really uncomfortable with the situation, I will not put a stop to it.”
A few moments later I could see Robert by the Maître d’ trying to find us. It is difficult to see Robert’s features from a distance. Once I get closer I can see he still has a youthful look to him though his hair is thinning on the top and his build is less athletic that at university. “Nice to see you,” a Robert embraces me and gives me a kiss on the forehead.
That kiss made my heart race and made me wetter, trying to hide my trembling voice, I said, “We are over here.” Robert and I arrive at the table and I introduce him to Dan. There is a few moments of awkward silence until Dan says, “Hey mate, glad you could join us on short notice. How about a pint?”
Robert, at first appears not knowing how to respond to Dan before taking a few moments and saying, “Not sure what you mean?”
“In England beer is served in pint glasses and much stronger, not the wimpy stuff they serve here. I believe in the States an English pint is 20 ounces?”
“I am not picky, surprise me.”
“What do you want Jen?”
“Nothing for me, I fine right now.”
“I will be back in a few.” By Dan getting the drinks I knew he was trying to set the right tone for the evening, checking to see if I want this to go ahead, and give me a few minutes alone with Robert. Trying to break the silence I ask Robert, “How have you been?”
“I have been all right, a lot has changed.”
“I suspected that.”
“I have thought about you a lot. I am glad you are here,” after saying that Robert bends forward kissing me on the cheek.
I respond by placing my hand on his inner thigh and looking into his eyes by quietly saying, “I know.” The intensity of the moment started my heart racing again, I began feeling warm all over, and I was feeling quite aroused. For a moment, the room felt as though it was spinning, I felt weak, and at that point, I knew my decision.
“Are you alright?” asked Robert.
“Not to worry, I will be fine.” I did not want to tip off Robert what I was thinking and I wanted to wait until Dan came back to let him know what I have planned. Looking towards the bar I could see Dan paying for the drinks and I started caressing Robert’s inner thigh some more. As I did I began moving my hand towards his balls and cock. The look on Robert’s face told me he was enjoying it. Once Dan came back to the table I said, “I want to go.”
I could see Robert’s face drop until Dan said, “I has been a long drive and I would like a drink before heading back to the room. Hey Mate can you do me a favour and take the misses back for me?”
Taking my hand, I gently stroked the outside of his hard cock, as Robert said, “sure.”
Dan and I did not plan this scenario. In order to make it look as natural as possible to Robert I said, “Dan was mentioning to me while you were getting drinks, some photographs he wanted to show me from high school. I know it would bore you. Do you mind if I see them.”
“Have fun, I will see you back at the room.”
The walk from the restaurant to Robert’s room was short walk from the restaurant since they were on the same floor. His room was a bit smaller than ours and it was noisier since it was poolside. Nonetheless, the noise of kids yelling, people jumping into the pool, and the running of the air conditioner to remove some of the humidity from the pool provided enough background noise where chitchatting became difficult. Robert sat on the chair by the table and door that lead out to the pool. I sat on the edge of the bed facing him. Looking at Robert, I could tell he was nervous and not sure what to do. He tried to talk about school but the nerves got the best of him. I knew if I did not do something soon then this whole journey would be a waste. “Look, Dan knows what we are doing here. My statement to Dan done in order not to tip off the other people what we had planned. No need to be nervous Dan’s know what we are about to do. He was the one that suggested it to me.”
“Yes. Dan and I do not do this all of the time… It is sort of a special thing this time. Now, are you going to get out of those clothes or do I have to rip them off of you?”
Robert then stood up and began undressing putting his clothes on the chair. As he did this I walked over to him putting my hand on his chest and began caressing his upper body before drawing him in close. Drawing him closely I took my right hand to feel his cock and I began kissing his body as I worked my way down to his raging hard-on. “I like what I see,” I said before taking his cock into my warm wet mouth. “Mmm…” I moaned and as I did Robert began thrusting his hips. At this point, I knew he is getting excited; I stopped, and guided him to the bed. After getting him to the lay on the bed, I instructed him to lay there as I undressed for him. Crawling on top of him, I took control by holding down his arms as I brought myself down so that I my face was in front of his cock. “I want you to be a good boy and follow my instructions, can you do that?”
The suggestion had taken him aback, as it had certainly not been what he’d expected the “favor” Jack to ask. He thought perhaps it might have been a case of moving a piece of furniture, or watching the cats for a day or two while Jack and his new wife went away. But no, the suggestion had left him a bit wide-eyed as he contemplated it.
“You want me to what?” Drew asked.
“Carrie and I were talking, and we both thought it would be great if you helped me have sex with her,” Jack repeated across the front seat of the truck.
“Wow,” Drew said, and turned his attention back to the highway ahead of them. “I mean, she’s hot and all, but…”
“But what?” Jack pressed.
“I don’t know,” Drew answered. “Just seems kinda, weird, you know?”
“Well, yeah, I admit it’s not something you ask your friend every day, but how about it?” Jack asked. Drew shrugged.
“I did always want to try that stuff,” he admitted. “I’ve really only done the one-on-one thing.”
“Before I’d met Carrie, that’s all I’d done too,” Jack added. “Of course, it’s not like I’m some kind of porn star now, but we’ve certainly played around a bit.”
“Really? Like what?” Drew was curious.
“Well, we’ve been with a few couples where Carrie’s played with the other chick,” Jack answered. “And a few times we’ve swapped partners.”
“Sweet,” Drew said. “Sounds like fun!”
“Then you’re in?” Jack asked. Drew thought a moment, and gave a nod.
“Yeah, why not?”
“Great! She’ll be happy to hear that,” Jack added, dialing his phone.
The night they’d gotten together later in the week had left each of the three of them anxious and ready, though all three were decidedly a bit nervous.
But that had given way to something very natural, very comfortable with one kiss, as Jack leaned in and began to kiss his wife, Drew sat and watched for a moment, feeling the stirring down below as the pair began to let their tongues play around each other’s lips before the kiss trailed off.
When they moved back in for the second kiss, Jack reached up to slide his hand along Carrie’s chest, and Drew leaned forward.
Hesitantly at first, he reached out and his hand slid up Carrie’s side, until he could move the hand around to the front where he felt Carrie’s right breast. It was soft, and it sent a tingle clear through him as the excitement of what was unfolding gathered in his mind.
Jack watched Drew give the breast a squeeze, and he smiled at Carrie, who smiled right back. Her hand traveled down to Drew’s, and she clutched the hand as it continued to play around her tits. Drew had moved over to lay a line of kisses down the side of her neck.
She let her head lazily droop to the side as the kisses continued along her neck, and Jack’s hands traveled down to her thighs, and began to stroke those while Drew leaned up to nibble on Carrie’s ear, and bring his other hand up to stroke the other of Carrie’s ample- yet not large- breasts.
She had a killer body, proportioned so nicely that Drew would have been lying to say he had not noticed it the first time Jack had introduced them.
Her ass was perfect, round and tight, with a nice pair of legs headed down from it. Her tits, as he had noted, were not particularly large, but were nicely shaped and felt great in his palms as he gave them another squeeze while Jack had run his right hand against Carrie’s pussy through her jeans.
“Maybe we should get… uh… a little more comfy,” Carrie said softly as the guys pulled back from her just a bit.
As they backed off, Carrie reached up to peel off the long sleeve t-shirt she had been wearing, and tossed the red shirt away to reveal a black bra underneath it. Drew was fixed on her as she reached back to undo the bra, while Jack was already beginning to peel off his own clothes.
At long last, Drew was pleased when the bra came away to reveal her tits, with erect nipples from all the attention and excitement. He then started to rid himself of his own clothing.
Within seconds, they had shed their clothing and were seated on the couch where the action had begun, all of them now totally naked. Drew and Jack were surprised at how comfy it had been, getting naked for a sexual encounter with another man in the room.
Perhaps it was the sight of Carrie’s ass as she had turned to sit on the couch that had helped keep anyone from feeling uncomfortable.
Carrie reached out with each hand, grasping each guy by the cock to begin stroking. Drew’s was larger than Jack’s but that didn’t really matter to her. The excitement of the situation was bubbling in her head as she heard each guy gasp and moan at the feel of her hand on their rod.
She was stroking slowly and deliberately as Drew was leaning in to lick her nipples, and Jack was back to kissing her left ear.
Jack then reached down to begin rubbing Carrie’s shaved, bald pussy. He was not surprised to find it already wet as his fingers slid between her folds, going back and forth in rhythm with her stroking of his cock. Drew had been moving back and forth, from one breast to the other to lick her pert nipples, sometimes gently using his teeth. Carrie let out a moan, and then smiled, with a slight giggle.
“You guys stand up,” she said.
Both men did as commanded, standing beside one another as Carrie moved to the center of the couch and took in the sigh of both hard cocks, throbbing directly in front of her. She smiled as she looked at the pair of them, then reached out with her hands to stroke each rod again as she scooted forward to the front edge of the couch.
Leaning forward, she ran her lips and tongue down one side of Drew’s cock, then moved back up and slid down the other side. He moaned, and she came back up to then open her mouth, letting his cock fill her. Her hands, meanwhile, were caressing Jack’s balls as he looked down to watch his wife sucking Drew’s cock.
Her head worked forward and back, forward and back in a nice, slow rhythm as Drew closed his eyes and smiled, almost unable to believe this was happening! He reached down to stroke her hair as she worked his dick in and out of her mouth, all the while using her hands to pleasure her husband’s rod.
Just a moment later, she switched, and Jack was only too glad to feel the hot mouth surround his member.
Drew reached down to give a squeeze to each of Carrie’s breasts before just leaning back to feel the hands on his cock and balls as she sucked her husband right next to him. She switched back and forth a few more times before Jack went to his knees in front of her while she continued to blow Drew.
He moved her legs apart to find her wet pussy in between them, and leaned forward to begin flicking his tongue across her clit, and into the folds of her mound. She moaned as she continued to suck the cock, and the hum from her moan made Drew quiver.
Jack’s face pressed in harder to Carrie’s pussy as Drew had his fingers in Carrie’s hair. Her sucking pace was faster, building with excitement as her husband devoured her pussy .
He worked a finger into the folds as she lifted her hips a bit higher, and Jack moved down to let his tongue begin to slither around Carrie’s ass, which tightened in excitement at the feel of that. The puckered hole quivered as the tongue moved back and forth across it, and Carrie reached down to grasp her husband by the hair in ecstasy.
After a while of this, Jack moved up, while Drew moved Carried further back on the couch, and lowered himself to put the head of his cock at her pussy. Jack had moved up so that Carrie could begin to suck on his cock again.
The big, hard cock slid nice and slow into Carrie’s hot folds, and she let out a slight squeal as she felt it sink in to the hilt, and Drew’s body pressed against her. He drew back, and then moved forward again, feeling the tightness and wet hotness of the pussy.
As he began to thrust in and out of the pussy, Carrie was feverishly working her husband’s cock in her mouth, and then slid back to lick the underside of his balls while he stroked his own rod.
He leaned forward to knead and palm her tits while she continued to lick his balls, getting the pounding from Drew as they remained on the couch.
Drew pulled out his cock, going down at once to begin lapping and nibbling at the now juicy pussy as Carrie reached down to grasp him by the hair in delight. Jack continued to guide his own cock in and out of her mouth as she moaned louder at the devouring of her mound.
But soon enough, Drew came up, grinning, and stood back away from the couch as Carrie removed the cock from her mouth to smile back.
“Are you quitting?” she asked slyly.
She slid forward off the couch on her hands and knees, and took Drew’s rod back into her mouth, immediately working it with her hands as well.
Jack was quick, and only too happy, to position himself behind his wife, and slide his cocky into her from behind, which promptly caused her to gasp around the cock, and let out a bit of a moaning squeal. He then grasped her by the hips, and began to thrust hard from behind her as she vigorously sucked Drew’s cock.
Reaching forward, Jack rubbed a finger around the pucker of Carrie’s asshole, bringing the finger back up to slick it up with his spit before returning to the hole to work the finger’s tip inside it.
Carrie, meanwhile, had relaxed her throat, and swallowed Drew’s cock all the way down, then came back up as he shuddered. She did it again, and he reached down to stroke her hair. Jack, meanwhile, had worked the finger into his wife’s ass, and started to slowly slide it in and out.
“Yes…” she purred. “Finger my ass…”
Still thrusting away, Jack continued to finger her ass while Drew enjoyed the sensation of her tongue flicking around the underside of his balls.
He began to stroke his own cock while she did this, also reaching back to tightly grip his ass cheeks. Jack had pulled his finger out, and slowed his strokes in Carrie’s pussy. He leaned forward to her.
“You want to try that thing I showed you in those pictures?” he asked, low, as he nibbled her ear.
“I do,” she whispered back at him. She then stood.
“Hey Drew,” Jack said, getting to his feet as well. “Why don’t you lay down on the floor there, in front of the couch?”
“What are we doing now?” Drew asked, still slowly stroking his cock.
“I’m going to have you in my pussy, while Jack fucks me in the ass,” Carrie said, stroking Drew’s chest and pausing to lightly pinch his nipples.
“Sounds good to me,” Drew said with a grin, and was quick to lay on his back, looking up as Carrie licked her fingers, and reached down to draw them across her pussy.
She narrowed her eyes on him and bit her bottom lip as she started to lower herself toward him. He held up his cock, pointed straight up as she came further and further down, and finally, using one of her hands, helped guide the cock into her.
“Oh yeah,” she shuddered, and began sliding up and down on the stiff rod.
Jack had gone to a drawer, and he took out a container of lube, which he opened and held over his cock. Some spilled out onto his manhood as he looked down in the dim lamplight to watch his beautiful wife bouncing up and down on his friend’s cock. He stroked the lube around onto his cock, and then approached the fucking pair.
His fingers spread some of the lube around on Carrie’s ass, while she and Drew had slowed their pace to allow for it.
Jack then positioned himself over her, and put the head of his cock to her asshole. She tensed, but he heard her giggle, and Drew leaned up to begin nibbling her nipples.
Slowly, the head of his cock worked into the tight hole, aided by the ample amount of lubrication. After the head was in, she pushed back on him slightly, taking in more and more of the cock.
Both Jack and drew felt the new sensation, a sort of full tightness that they could feel with both their dicks inside her. As soon as Carrie had pushed back to the point where Jack was all the way in, they all began moving.
It was just a bit hard at first to get the rhythm, and twice Jack’s cock had come out of the hot, tight ass. But soon enough, they had managed to find a rhythmic pattern to each of their moves, and Carrie let forth a louder, pleasurable moan.
“You like that?” Jack asked. “You like the way that feels?”
“Oh… yes…” she uttered.
They continued to move, faster and faster with both of their cocks working in and out of the holes until all three of them were making louder noises, and the sex was building to a fever pitch. Carrie put a hand on either of them.
“Cum! Now!” she managed to gasp at them as Jack held her waist and Drew had her hips. She could feel them both swelling inside her, and a moment later, each of them had pulled out of her, with blasts of hot, white cum pulsing from them, and onto her.
As she felt the cum slithering its way around her and them, she glanced over her shoulder at her husband, whose eyes were closed and his head back as he stroked out the last of his cum.
“Hmmm..” she said, drawing his attention as Drew had continued to softly massage her tits. “Might have to make this a regular habit.”
Jack smiled at her.