best friends

He looked so frail and vulnerable laying there. I knew that my friend Anthony was troubled, but I never knew he would do something like this. Good thing the doctors got his stomach pumped out in time. I have known Anthony since elementary school and he was always different. Shy and introverted was the norm for him. He never really fit in anywhere. Seemed the only time he came out of his shell was around his Mom, his sister or me. Anna and I dated for a while, but we just sort of grew apart. So Anthony and I hung out together till High school graduation. I had enlisted in the Air Force on the notion that I would get the training I needed for a civilian career. I had just been discharged from Uncle Sam’s employment and was about to start a new job when I got the call.

His Mom sounded so desperate over the phone. She pleaded with me to come down to the hospital to see him. I wanted to get back in touch with Anthony anyway. I didn’t even think twice. After hugging her and Anna, and participating in a mutual consoling section, I sat down in a chair while the two of them took a break to get coffee.

I looked at his face. It was always lean and strangely angelic. I had seen pictures of his deceased father and he definitely favored his mother Alice. He seemed peaceful, almost childlike. His long dark hair, was pulled back in a pony tail. I thought back over the years of our friendship. I was so glad that the doctors were in time. He stirred.

I took his hand and he looked up at me. His expression was half elation and half shame. “T–Troy?” He turned away from me.

“Why Anthony? Why did you do this? You had us worried.”

“You don’t know what it’s like Troy. I don’t seem to fit in anywhere. Everybody else has a life but I don’t.” Tears tracked down his cheeks.

I couldn’t be mad at him. “Well Bud, good thing I’m going to be around because if you try that again and I’ll kick that Puerto Rican butt of yours down the block.”

Anthony brightened up. “You mean…?”

“Yep, you are stuck with me. I am honorably discharged out of the Air Force and I start work at a security and logistics firm, here in town, next week. So I’m going to be keeping an eye on you.” At last Anthony smiled.

Because of his suicide attempt, Anthony was ordered by the court to have psychotherapy. I tried to make it to his house to visit, at least once a week. I was always treated like part of the family. Mrs. Gomez made wonderful meals and I had a standing invite for supper any day. I don’t know if it was because I was over often or what, but Anthony seemed cheerier somehow. Anthony stayed in therapy long past the court mandate; in fact he started seeing another therapist as well. I found this curious, but at the same time I was pleased at his progress. He laughed more often and the family in general seemed happier.

One evening Anthony popped over to my apartment unannounced. It was a year almost to the day of his attempt on his own life. I had been real busy as of late and hadn’t been over to the Gomez household for almost two months. I had just got in and saw someone in front of my apartment door. I thought it was a chick at first, in fact it took me a few moments before I realized who it was.

“Anthony? Hey buddy, how you been?” The person before me looked neither male or female, but sort of an amalgam of the two. He wore a hoody and jeans.

“Hi Troy. I’ve… been okay. Can we talk?” I nodded and open the door. I followed him inside and pulled a couple cans of soda from the fridge. We sat at the kitchen table. The light was better than in the hallway. His face had cleared up and he seemed softer somehow. His eyelashes looked longer than I had ever seen them before. In fact, his eyes were sort of pretty. I just sat there.

“Do I look different to you?” He had a wry smile, that projected more confidence then I had ever seen from him before.

“A bit Anthony.” I was afraid to say anything more.

“You know I continued seeing a psychiatrist.” I nodded. “I discovered something about myself. Through talking with the Dr. I found out something. It seems my brain is hardwired as female.” Anthony paused to let this sink in. “Makes sense really. It explains why when I check out girls, that I feel a twinge of jealousy and why I like looking at guys asses. That really use to bothered me.”

I listened to him; half in shock and half in curiosity. He was different somehow. Even his mannerisms and gestures were smoother and not clumsy as usual.

“Mom and Anna are okay with it. They surprised me by being so supportive. I started hormones, almost a month and a half ago. I feel so alive, maybe for the first time in my life.” His eyes narrowed. “Aren’t you going to say anything?”

“G–Good for y-you.” I stuttered. I was flabbergasted. In my wildest imagination, I could have never come up with this scenario. I looked into Anthony’s soft brown eyes. It was like there was this beautiful creature, that was slowly emerging.

“I’ve been in girl mode for close to a month. I dressed in my old clothes tonight so I wouldn’t startle you too much. So you are cool with this?”

“S-Sure A-Anthony.” He/ she smiled in relief. “I want you to be happy, Anth–.”

“I am changing my name to Alison Marie, Troy.” She interrupted as she stood up.

“T-That’s an nice name, Anth– I mean Alison.”

“I need to use your bathroom. Be back in a jiff.”

To say I was stunned was an understatement. Anthony was always different, even around me. This was the most confidence he had ever had to my knowledge. I have heard about transgender people before, but that it would actually be one of my friends really floored me. Don’t get me wrong, I am a live and let live kind of a guy. It’s none of my business to tell someone else how to live. To me all people are equal and have equal rights.

Minutes later Anth- I mean Alison reemerged. I stood and was totally stunned by his/ her appearance. I mean, the hood on the sweatshirt was pulled back and he; I really couldn’t say he anymore; she was wearing makeup. Her hair was gathered back in a ponytail and was very attractive. Her eyes were beautiful and her lips…What the fuck am I thinking?

“I hope you don’t mind. I feel naked without makeup now.” As she approached, I could smell the fragrance she applied. She leaned over, kissed my cheek and winked. “See you around Troy Boy.” Moments later Alison was gone.

“Curiouser and curiouser.” I said to myself.

Another month went by till I found myself at the Gomez residence again. Anna called me up and told me that her Mom was ticked cause I hadn’t been over for dinner. I had been holding off because of my strange encounter with Anthony/ Alison.

Mrs. G let me in and hugged me. “About time you showed up Troy. I was beginning to think you forgot about us.” We entered the kitchen. Her dinner smell extraordinary. “I hope you don’t mind Italian, Troy”

“No, Mrs. G. It smells…” I felt a tap on my shoulder. I turned and Anna threw her arms around my neck and hugged me.

“Hey Troy. Glad you could make it.” She seemed more affectionate than usual. Like she was really pleased. When we stopped dating, it sort of cooled down fast, but this was more like the old Anna.

“My turn, Troy Boy.” Alison appeared as if by magic. She; there was no getting around this; she was beautiful. She was wearing hip hugger jeans and a pink, belly T shirt. Alice had her ears pierced with hoops, she smelled fantastic and her long, dark hair was done in ‘gypsy’ curls. Her arms flew around my neck. My own arms went around her waist out of reflex. She kissed my cheek.

I heard a soft giggle behind me. “You two want to be alone?” Anna piped up.

Alison, still in my arms, gave me a saucy wink. “Well, now that you mention…”

“Wow, that food smells great!” I interrupted. By now I was probably as red as a fire hydrant.

We sat down at the table and soon our plates were filled. Mrs. G fixed stuffed shells, salad and breadsticks. Her cooking was wonderful as always. I gazed at my dinner companions. I am attracted to Hispanic women to begin with and their Puerto Rican heritage certainly fit the bill. Even Mrs. G, in her mid forties was still hot. But what killed me was the startling resemblance of Anna and Alison to each other. They were born twins, but since Antho- Alison’s transition; they looked almost identical. Even their voices were similar.

“Well, what do you think of our Alison?” Mrs. Gomez seemed quite proud of her new daughter. I quickly crammed a huge bite of food in my mouth, giving me time to think of an appropriate answer.

“I’m getting my boobs next week.” Alison blurted. I choked on the bite of salad. Alison, who was setting next to me thumped my back with her hand as I tried to cough up the food.

“I think you startled your boyfriend Alison.” Anna giggled. I began to cough in earnest.

“Now Anna. We mustn’t tease Troy like that.” Mrs. Gomez remarked. But that didn’t stop her from smirking.

After dinner and when the dishes were taken care of, we played cards. This was at a card table in the other room and one of the three was playing footsy with me, off and on all evening. I never did find out who. I hoped the Hell it was Anna. Because it would be really awkward if it was one of the other two.

Sometime after midnight, Mrs. Gomez and Alison got to the point where they couldn’t stop yawning. They both excused themselves and Anna volunteered to walk me to my truck. Outside she raised up and kissed me on the cheek and headed back into the house. She was so beautiful. I wondered if she would want to get together again and start up the old flame.

I slid behind the wheel and stopped when I saw that Anna had come back outside. She walked up to the car and I jumped out. “Hey Anna. Did you want something?” In one fell swoop, she slipped her arms around my neck and soon her lips were pressed up against mine. I forgot how great of a kisser she was. I wrapped my arms around her waist and really sunk into the moment. Her tongue slipped into my mouth and the race was on. Her tits were pressed up against me and she felt so good in my arms. Anna reached behind her and pushed one of my hands down to her ass. She moaned when I grabbed her other cheek on my own. All the while she was grinding her hip into my growing erection. There was a time, back when we were first dating, that she was almost insatiable. This was just like then and man, did I need it!

Anna backed off and reached behind my front seat for the sleeping bag I kept there. She giggled and took my hand, leading me back to the bed of my truck. I can’t remember how many times we utilized our ‘fuck station’. But it was real handy and it stayed mostly empty for spur of the moment use. It had been a while, it appears it was time again to test out the truck springs.

Soon the bedding was unrolled and we were kissing again. I reached for her breast and she batted my hand away. “Let me do all the work.” She whispered lustily. Well, it was okay by me. I lay on my back and she straddled my body. Anna’s hands held mine to the truck bed as her tongue was crammed down my throat. She wiggled her ass against my engorged cock and undid my shirt buttons, one by one. Anna slid down and sucked on my nipples, as my erection threatened to gore her stomach.

“Oh, somebody’s happy.” She whispered. She slid down some more and undid my pants. They disappeared as if by magic along with my briefs. Soon my hard cock was in her hands and Anna started stroking me. Her hand worked me over good. It was slow and steady. Every time I was close, she would clamp down to avoid the inevitable. “I’m going to suck you now.”

Anna kept a firm hold of me to keep me from coming, all the while she slathered my cock with her lips and tongue. It was pure torture and I need to cum so badly. I tell you, I think interrogators use the wrong tactics to get information. Christ; I would have been willing to give her anything I had if she would just let me cum. Finally and mercifully Anna released me and I shot into her mouth over and over. I damn near passed out, it was so intense. It was hard to tell in the low light, but I had the feeling that she sucked down every drop.

“Did you like that, Baby? She whispered.

“Fuck yes, Anna.” I fought to catch my breath. “Come up here and I will eat that sweet pussy of yours.”

She slid next to me and we kissed. “Sorry Baby, but it’s my time of the month. Maybe next time. It’s getting late.” She kissed me again and whispered in my ear. “I love you Troy.” And like that, she was gone.

I laid there, mostly naked and felt like I had just survived a hurricane. After a few moments I slipped back into my clothes and started for home. It seemed that Anna was even wilder than she use to be and that suited me just fine. That was the hottest blowjob I had ever gotten. I wondered how long it would be before I could return the favor. I hope not long.


I got busy again. Another month and a half vanished and I was out of town for most of those six weeks. I thought about Anna quite often. I mulled over her last words to me. ‘I love you Troy’. It’s not that I couldn’t appreciate what she professed, but I had to spend a lot more time with her before I could feel the same. And I didn’t want to take advantage of her, more than I already had.

I finally returned home and I decided to give Anna a call. Before I flipped open my phone, it went off. “Hey Troy, how are you?”

“I’m good beautiful. I was just thinking of you and the last night we spent together. I really felt close to you Anna.”

Her answer didn’t come right away. “We just had dinner and played cards, Troy.”

“I was thinking of what went on afterwards Baby.”

She giggled. “You must have been really hard up to get your jollies from a kiss on the cheek, Troy.”

“No, Baby. I meant what happened afterwards.”

“Afterwards, I went to bed. That was it.”

What? My mind was reeling. “You didn’t come back out?”

“No, I didn’t. But could you look in on Alison for me? Mom and I are out of town visiting friends and she is by herself. Please Troy.”

I set there, totally stunned. If it wasn’t Anna, then it could have only been her Mom or —–.

“Troy, you there?”

“The night I was at your house, was your Mom awake when you went inside?”

“Alison was the only one still up. She passed me in the hall on the way out to take a walk. Could you look in on her, Troy?”

“S—Sure, Anna. I’ll do that.”

Anna told me that Alison was home and then hung up. It was Alison that I made out with? I didn’t know what to feel. I didn’t know if I should be pissed or flattered; turned on or turned off. Being honest with myself, Alison had to be the best kisser I ever had in my arms, not to mention the blow job. But that wasn’t really fair to her or me. I guess that I should call her and get this straightened out. When she answered the phone I told her that I had something to talk to her about and it was very important. She said that she was at home and would be expecting me.

On the drive over I rehearsed what I was going to say. I was going to tell her that, even though we were friends, that a romantic relationship between us wouldn’t work. I tooled up the driveway and was soon at the front door. I would just have to lay it on the line to Alison. Make her see that it wouldn’t work. The door started to open. I would just have to be firm and —-tell—-her— like— it—. Judas Priest!

Alison stood in the doorway. Her coy smile wasn’t the only thing that stunned me. She wore cut off jeans and a lavender blouse that showed off enough cleavage to make a bulldog break his chain. Her makeup was perfect. Smokey lavender eye shadow accentuated the most beautiful eyes I had ever seen and her lips took on the color of succulent black cherries. She looked like she just stepped out of a glamour photo shoot and It looked to me like I was in deep shit.

Alison blushed. “Hey, Troy. Nice of you to look in on me.” She cupped her new breasts. “How do you like them? I am so glad I don’t have to wear those fake breast forms anymore. Come on in. What was so important?”

My mouth was dry and for some reason I forgot the reason I was there in the first place. “W–Wow, Alison. You look—really—great!” We walked through the foyer and ended up in the kitchen.

“Thank you Troy. Now what was so important?” She repeated.

I would have liked to have said something that James Bond would have rattled off to get his latest conquest into the sack. I just stood there like a lovesick fool, about drool all over himself. But it was the truth though.

Alison’s eyes sparkled. “You suspected it was me that you were kissing, that night.” I nodded like a total idiot. She stepped forward and her scent overwhelmed me. Her arms slipped around my neck. “You wanted to see if it was true.”

We were nose to nose. “I-I-I n-n-need to talk to you.”

Alison huskily whispered in my ear. “What do you want to say to me, Troy?’

I swear I was about to answer. I licked my lips and then so did Alison. Her tongue slithered into my mouth and my arms circled her waist. The last of my willpower faded as she pressed herself up to me. With an incredible effort I pushed her backwards, against the wall. Alison’s eyes widened, wondering what I was about to do to her. She groaned when my lips found the nape of her neck. I was lost in what I was doing as Alison ground her body into mine. Her mouth found mine again and I thought she was going to suck the life out of me.

I pulled back. “You are so damn hot Anthony…….” The realization of who she use to be hit me. “No… this is wrong. We shouldn’t be doing this.” I reeled away and headed for the door.

“Troy!” I heard Alison cry.

I didn’t care. What the fuck was I doing? Alison use to be a guy for Christ’s sake. And my friend to boot. I headed for my Jeep. I slid behind the wheel and was soon backing out of the driveway. I looked up in the rearview mirror out of habit and romped on the brakes. Alison was standing there, in my way, with tears running down her cheeks.

“Move Alison!” I commanded.

“No, I won’t move till you hear what I have to say Troy.” She yelled in return.

“I’m warning you Ali. Get out of the way.”

“You’re going to have to run me over then, Troy Boy, ’cause I’m not going to budge.”

I blew out a exasperated breath and turned off the ignition. This situation had got way out of hand and maybe I overreacted. But I should have never let it get this far in the first place. I don’t know what I was thinking. She was so damn beautiful, that I let my dick do all the thinking for me. Then when she wouldn’t let me leave, it floored me. I was so stunned that Alison could be so stubborn. Anthony was never like this. He was such a pushover that he went along with everything I said. But not Alison. I got out and she walked up to me. Her eyes were narrowed and she looked determined enough to chew steel and spit out nails.

She wagged a finger at me. “Troy Andrew Malone. Listen to me and listen well, buster.” God, I couldn’t help thinking how hot she looked! ” And you’re going to keep that trap of your’s shut till I’ve had my say. You hear me?”

“Yes Ma’am.” I squeaked.

“Good! Now listen up. My attempt at suicide turned out to be a blessing in disguise. The psychological counseling was my wake up call. Anthony, never knew where he stood or where he was going. As Alison I have learned so much about myself. I can do things that I never thought was possible before. I now have the courage to live life and not just let it pass me by.”

“That’s..” I started. She shushed me and continued.

“I never felt any confidence as a guy, but this transition has opened up feelings in me that I never even knew existed till now. And some of those feelings are about you. I hated it back when Anna was leading you on. She just wanted to use you and that was it. She has done it before, with other guys. But this time it was different. I was actually furious that she hurt you. The sessions with the therapist made me realize how much I really do care for you.” Her head drooped a bit and she averted her eyes.

I was startled awake by a loud crash. My heart pumping, I listened carefully and then relaxed a little. It was just someone was up and doing things downstairs.

I lay back down but the adrenaline rush wouldn’t let me fall back to sleep. I was in bed with my friend Jon and his door didn’t have a lock. If someone walked in on us, like his parents or sister sometimes did…

Of course I had stayed overnight at Jon’s lots of times in the years we had been friends. But one of us would always take the floor. We hadn’t slept in the same bed since we were kids.

Yesterday Jon and I fooled around with each other. I guess you could say we had sex. It was pretty damn hot and just thinking about it was making my dick throb.

I took a look at Jon. I had fallen asleep with his arms around me, and now we were lying side-by-side on our backs. His face was half-covered by his long brown hair and he looked kind of sweet. I turned onto my side so I was facing him.

I touched his face, letting my fingers trail down to his chest. He twitched when I got down to his nipples. I rubbed at them, feeling them stiffen under my touch.

The sheet was covering him from the waist down but I could see his erection tenting it out. I took his dick in my hand and stroked it lightly through the cloth, feeling it get even bigger while I touched him.

Fondling his dick was getting me hornier than ever. Pushing the sheet away, I slid up even closer to him and pressed my erection against his bare thigh. I grasped him again, feeling his hot skin against my palm.

I looked at him closely. He still seemed to be asleep. His dick was oozing out pre-come and I moved my head down to it. Taking hold his balls, I ran my tongue around his dick head and licked up his streaming juice.

Lowering my head down, I took his dick in my mouth and sucked on it gently. I was really getting into the feeling of having a dick pushing against my tongue. Funny how not even 24 hours ago I hadn’t even thought of trying that. And now I couldn’t get enough.

I felt Jon’s hand on the back of my head. Since he was awake I switched to working him faster and stronger. It didn’t take long before his hips started bucking and his dick pulsed. He came right into my mouth. After his first couple of shots I pulled back and gripped his dick while he kept on spraying all over his chest.

I slid back up the bed so we were face-to-face. He had a dazed look on his face, like he didn’t know what had just happened.

“Jase. Wow,” he said, smiling at me. “That was so…fucking amazing.”

Without a word I grabbed his hand and moved it right to my aching dick. He stroked me for a couple of minutes and then shimmied down the bed, not wasting any time in getting his mouth busy. I lay back and closed my eyes, clenching the sheets in an effort to keep quiet. I could still hear people messing around downstairs and I was a little freaked about getting caught.

But I was super-horny and I couldn’t stop from moaning from Jon’s awesome blow job. He was using just his tongue on me, licking and teasing right around the edges of my dick head. When he started playing with my balls at the same time, I lost it. I came so hard I couldn’t hold back a groan. My cum shot everywhere.

Jon climbed on top of me, causing our sticky stomachs and wet cocks to rub together. His head was inches from mine and I looked up at him. Our lips met at the same time and we kissed hard and long. I felt his dick stiffening against me and then we froze.

Both of us heard voices in the hallway. They passed by the bedroom without stopping, but we were too freaked out to keep going.

Jon rolled off me and lay on his back, resting his hand on his semi-erect dick.

“I think they’re gone. But if we don’t get up soon someone will come and get us. Go on and shower first.”

I pulled on my shorts and t-shirt before I opened the door a crack and checked the hallway. Seeing no-one, I hurried down to the bathroom.

I stood under the water, washing myself and tried not to think about what Jon and I had done. But I couldn’t help it. While I washed myself off and thought about him, my excitement grew.

When my dick got so hard it was standing straight up against my stomach, I couldn’t resist. I soaped up my hands and used both of them to stroke my dick rapidly. I was so into what I was doing I hadn’t noticed the bathroom door opening.

I looked up and nearly jumped out of my skin when I saw Jon standing there, naked and hard. His clothes were on the floor beside mine.

He climbed into the shower behind me and wrapped his arms around my chest. He ran his hands all over my body and when he got to my erection I shivered at his touch. I felt his stiff dick rubbing against my ass in time with his stroking. It felt so good I was already close to cumming.

He kept rubbing my soapy dick with one hand and with the other he grabbed my slick balls, fondling and squeezing them. I felt my orgasm rising up, racing through my dick and exploding out of me.

I leaned back against Jon for a moment, still feeling his hard-on rubbing between my ass cheeks. I thought he wanted to fuck me and I wasn’t sure I could go through with it. It was a scary thought, having a dick buried deep inside of me.

But he just kept sliding his dick between my cheeks. He was gripping my hips now and really grinding against me. I braced myself against the wall and thrust my ass back against him, loving the feeling of his erection and wanting to make him feel good. His strokes got faster and faster and then he grunted. I felt his hot come shoot up my back.

He pulled me into him and hugged me from behind. “We better hurry,” he said after a moment. “We’re supposed to be downstairs in a few minutes.”

We started washing each other off and kissing. Jon was busy washing my dick off very carefully and I was about to start on his when someone banged on the door.

“Hurry, Jon, Jason, whichever one of you is in there. It’s breakfast time.”

Jon called out a reply and reluctantly I moved so I could rinse myself off.

After we had dried off and gotten dressed I stuck my head out the door to make sure we were alone. Jon took the opportunity to stand behind me and fondle my ass.

“Stop it,” I told him, swatting lightly at his hand. I could feel my dick reacting to him just from that little bit of contact. He just squeezed my ass and gave me a grin.

Brian, Jesse, and I have been friends for well over a decade; we came out of high school at the same time, they as a couple and me looking, as I am still.

Brian and I are alike in stature, slightly over 6 feet and 200 lbs. Jesse is a petite blonde bombshell with a runners body and hair that reached her middle back. The thing is though, she bugs me.

With flashing wit and relentless sarcasm she seems to delight in making fun of me from my choices in women to the last haircut I got that turned out rather choppy, and every chance she got she would smack me across the back of my head, either with her hand or “accidently” with her elbow.

One night we were sitting around their dining room table playing cards and listening to some good blues music when she got in a particularly good zinger on me, then proceeded to get up she elbowed me in the back of my head.

“Oops, sorry.” she laughed as she glided past me to freshen our drinks.

I looked at Brian and shook my head. He was laughing out loud when she came back to the table with the drinks. We were catching a bit of a buzz with the killer weed we were smoking.

“You know.” I said looking directly at her. “One of these days you are going to earn a spanking so sound you won’t be able to sit for a week.”

“Oh yeah?” she replied defiantly. “I dare you.”

Standing again she stuck her tongue out at me and walked the long way around the table to avoid me.

“I’ll even let Brian watch because I know how much you bug him too.” I called after her as she went into the kitchen to get some munchies.

“Oh BoodilyHoo” she called back over her shoulder as I watched that fine ass shape shift the back of her skirt.

A few minutes later she came back with a bowl of chips and set them down just out of Brians’ and my reach.

“Mine.” she laughed as she danced back towards the kitchen, stopping for a second to once again slap the back of my head.

Screw it, I thought, and spinning my chair on one leg I reached out and grabbed her around her slim waist. Pulling her between my legs I locked her to me.

“Beast.” she laughed as I looked over my shoulder at Brian. “Do you want to move your chair so you can get a better view of this buddy?” I looked at Brian inquiringly as I held his squirming girlfriend against my crotch and smacked her once on a full, round ass cheek.

She jumped at the gentle smack, rubbing her leg against my stiffening cock, but was more surprised, I think, at Brians’ reply.

“Hell yeah I do.” Was all he said as he moved his own chair in front of us and sat leaning forward.

With my legs wrapped around hers and my left arm holding her arms against her body I took my right hand and slowly moved it to the hem of her skirt.

“The only good spanking is a bare bum spanking.” I said watching Brians’ face for a reaction as my fingers started to raise the hem of her skirt.

He smiled and nodded. That was enough for me.

“Hey!” Jesse cried, laughing, when my hand rudely pulled her skirt up over her hips. She tried to push it back down but her trapped arms offered limited movement. “Don’t! Stop!” “All right.” I pretended not to understand her. “I won’t stop.” I then reached my right arm around her body to take her right wrist in my hand and deliver it to my left hand. Holding both her wrists in my left hand now I returned to her ass with my right and finished lifting her skirt over her full hips.

She wiggled against my control but was powerless as my thumb hooked the waistline of her panties and began to pull them down to expose her full, ripe bottom.

“You are going to let him do this?” She raised an eyebrow at Brian, still laughing and struggling, causing the bulge in my jeans to expand. I knew she could feel it against her leg and enjoyed that thought.

“Hell, I may help him.” Brian grinned as he watched her struggle in my arms.

With a resigned sigh Jesse stopped struggling so much, but continued to rub my crotch, still teasing me.

“I guess after all these years of my abusing you, you do deserve a time of redemption.”

My heart raced as I let go of her wrists and reached to hitch her skirt further up her hips. I then released her legs from mine and pulled her panties all the way down to her knees. Grasping her torso and her legs in my arms I lifted her onto my lap with her legs dangling to the floor and her arms over the other side of my lap. Totally exposed to my view for the very first time I paused to admire her, rubbing my rough hand over first one cheek and then the other. Her skin seemed to glow white under my hand while I rested my left arm across her back, my fingers brushing against the fullness of her breast.

Lifting my right hand from her I brought it down lightly on her right cheek, not hard enough to leave a mark, but hard enough for me to watch it ripple and move.

My cock was really beginning to throb. Caught between my leg and the hardness of her stomach I knew she could feel the heat of it against her.

I raised my hand and brought it down. I struck with a sharp slap before continuing in an arc to come back to her other cheek in an upward motion. This was hard enough to make good noise but not to leave a handprint.

I felt her wiggle on my lap when I said “I am not going to hurt you much Jess, but by the time I am finished your ass will be rosy red and hot to the touch.”

She looked back at me and actually smiled shyly. “Ok.” was all she whispered.

I started bringing my hand down in a rapid pattern, lightly slapping in a circular motion until I began to see both cheeks start to redden. Jesse sighed gently when I rested my large hand on her cheeks and stroked, letting my pinkie finger slip down the crack of her ass to her slightly parted legs.

“Not too bad so far is it?” I was curious as to how far I could go as my hand continued to caress her cheeks.

“Nope.” she murmured.

Suddenly I brought my hand up and brought it down with a sharper slap, making her jump in my lap slightly while I enjoyed all the sensations; from the sound to the sight of her quivering cheek and deepening redness.

Bringing my hand back I moved it with a little more force, contacting both of her cheeks at the same time and moving her body across my legs as she pushed against the floor with her toes.

This made me harder, feeling her body move against my cock the way it did. “Hey Brian” I called. “Did you like the way her body moved with that last smack?”

Brian nodded his approval while watching my hand massaged her reddening butt. “It gives me an idea actually.” He said as he rose to his feet unbuckling his belt.

Jesses’ eyes widened while she considered what he might have in mind with his belt in his hands.

“I don’t want to strap her, man.” I declined quickly

He laughed. “No.” he said. I have something else in mind. How about this? I fuck her mouth while you drive her into me with your hand?”

Jesse said nothing while I considered, finally saying “It is ok with me if it is ok with Jesse.”

With her right hand around my ankle and left around the chair leg I felt her start to push herself up. “Really?” She breathed. Suddenly lowering her voice she said. “Yes please, but first.” She then pushed herself off my lap and stood. Positioning herself so she could see her boyfriend she lowered her panties all the way to her ankles and stepped out of them. She then undid her skirt and let it drop too.

“Those were uncomfortable.” she informed us before starting to move back to my lap, in the process giving me a glimpse of her totally hairless pussy.

I stopped her with an upraised hand. “In that case,” I reached for the top button of her blouse. “Those buttons and that bra are uncomfortable on my lap.

She giggled and said. “Not to mention you jeans zipper Tim. We may as well get really comfortable.”

We finished undressing each other as Brian looked on approvingly. I then sat back down in my chair and guided her back to my lap. This time there was nothing between my throbbing erection and her naked skin and it thrilled me.

My right hand went back to her ass with a quick slap. She gripped my ankle and spread her legs at first contact. I could now stroke all of her and took advantage while Brian watched us with his cock in his hand.

I ran my left hand down the center of her spine while my right hand reached down to one knee and back up as I raked my nails lightly up her inner thigh. I flattened my palm against her hot skin and pressed my finger against her soft pussy lips.

I felt the hardness of her back muscles tighten when my hand brushed her pussy lips. She was wet against my fingers already. I twisted my hand between her legs so that I could get a finger or two inside.

Feeling her shudder against my legs I pressed my fingers into her wetness. My knuckles spread her lips easily. “Oh my.” She sighed as my middle fingers explored her pussy and my thumb pressed against her ass hole.

Brian watched my hand in his girlfriends’ pussy with interest as I drew it out and started spreading her juices on her cheeks. “This may sting a little more.” I told her before raising, then bringing my hand down.

A loud ringing slap filled the air along with her deep intake of breath. I had left a good handprint this time, though it took a moment to appear. I moved my hand back to her pussy, rubbing vigorously and reaching for her clit.

Looking up at Brian I smiled. “There is just one more thing I want to do before moving on to your plan.” He nodded wordlessly as I widened my legs for better support and reached my left hand to Jesses’ cheeks. I held them apart while sliding my fingers inside her wet honey pot, then leaning in, I spat on her asshole.

She gasped as my thumb began to massage it into her little hole, lubricating it even more. I then slid my thumb slowly inside her while at the same time I fucked her with my fingers.

Jesse didn’t seem to mind the intrusion of my hand into both her wet holes so I stroked her insides for a few minutes, first fingers in her pussy, then sliding out while my thumb entered her beautiful ass. She sighed deeply while digging her fingernails into my leg.

Taking my hand away from her I looked up at Brian and brought my fingers, drenched with her juices, to my mouth and licked them clean.

He smiled when I said. “Oh man she is sweet.” Nodding his head in agreement as he stepped towards her face.

I shifted my legs again; reaching under her I took a breast in my hand as she reached for Brians’ knees to hold her up slightly and opened her mouth to him. He slipped the head of his cock past her lips and raised one hand to me as a signal for me to hold back.

I stroked Jesses’ ass and pussy while Brian positioned himself. He then took Jesses’ face in his hands and slid a little deeper into her mouth and nodded to me.

Jesses’ head was tilted back so I knew he was going to have good access. I moved my hand back and then swept up in one motion. Striking her ass with a loud slap I watched her lurch forward with a little help from my legs moving with her, lessening the force of this spanking.

I let my hand stroke and sooth her ever reddening cheeks before moving it back for another strike. This time I slapped her lightly while moving my legs to the left and driving her mouth onto his cock and her nose into his stomach.

I held her there and could tell she was swallowing the head of his cock into her throat. I let my fingers go back inside her pussy and felt her shiver again against my legs.

Moving her away from the base of his cock I gave her time to breathe while I finger fucked her, listening to her moan against his cock while my own was dripping juice between my body and hers, making greasy contact.

My fingers sliding out of her pussy, she moaned louder. Knowing she was going to be fucked slowly and carefully she was fully drenched now. I brought my hand back for another pass, ringing it sharply off her cheek I moved my legs again and she took all of him.

With Brian fully inside her mouth and throat I began lightly spanking again, working at bringing heat to her ass and inner thighs without causing too much pain. She turned a nice shade against the ministrations of my hand while the fingers of my left hand gently pinched and pulled her nipple.

“One more, a good one just like the last one and then you can give her a try.” Brian said looking down at Jesses’ reddening cheeks and legs.

I moved my legs back so she could suck on his head for a little bit. I then spread Jesse even wider. She looked so good on my lap with her boyfriend in her mouth I wanted to make her cum, so I drove my fingers into her, my knuckles widening her as I alternately entered her pussy and stoked her clit.

She began to moan louder and move against my hand of her own accord. Hungry for it, she began to inhale Brians cock as her pussy tightened around my fingers and her orgasm began.

Feeling this, I quickly moved my legs without spanking her, keeping my fingers inside her instead. I moved her body with my rhythm, sliding Brian down her throat as my hand pressed hard inside her.

I could feel her orgasm taking her, gripping my fingers as she shook her head back and forth on Brians cock.

She pushed against Brian and lifted her head away from him so she could scream “Oh fuck yes!” Humping and bucking her pussy against my hand before collapsing completely.

My hand and leg was soaked with her, so I used her own juices to sooth her hot red ass cheeks in gentle circles. Looking up I asked Brian. “So what did you have in mind?”

Kneeling, he took Jesses’ face in his hands and kissed her slowly and deeply while I rubbed her sore cheeks. Breaking the kiss he looked at me and said “Well buddy, I was thinking I would fuck her and she could blow you for a while. If you stand I can drive her into you the same way you did for me.”

The room was beginning to smell of really hot sex, with three bodies sweating with excitement and exertions. I stood Jesse up and guided her between my legs, looking her up and down. She blushed suddenly when my hands pulled her to me and I kissed her breasts, going from one to the other with my tongue flicking and licking each nipple in turn, making them achieve incredible hardness.

“Sounds good to me man” I answered, still kissing her hot flesh. “But first there is one thing I want.” Standing, I turned her in a little dance until her back was to the chair. “I want to taste more of this spicy slut.” I told him as I sat her down and spread her knees.

Kneeling in front of her I lifted her legs over my shoulders and she obliged me by moving to the edge of the chair.

I moved my face to her sweetly glistening pussy. Flicking my tongue out I lapped her glowing thighs, moving from one to the other to lick her cum from her before concentrating my attention to her pussy.

I licked up the entire length of her slit as she grasped the back of my head, holding me there. My tongue worked between her lips and went as deeply as it could inside her. Pressing my face I mashed her lips with mine and then began shaking my head back and forth gently, making contact on her clit with my nose.

Withdrawing my tongue I took those puffy lips of hers into my mouth, sucking as my nose continued to rub her clit, and then reaching over her leg I moved my hand to her clit, pinching her distended button between my fingers while sucking and pulling on her lips.

Jesse moaned when I suddenly released with my mouth but not with my fingers. I had her clit isolated now and could see it glisten in front of my eyes. I flicked my tongue across it making her squirm before I removed my fingers and sucked it hard into my mouth.

“Oh fuck!” She cried while my tongue made a tour around her overly sensitized nub. My lips spat it out and sucked it back in before I once again plunged my tongue inside her pussy.

I held my face against her for a few moments more, drinking in her juices and coating myself with her essence.

Brian stepped up to the side of the chair and reached for Jesses arm. Looking at my wet, grinning face he said. “Come on Tim, its time to fuck the hell out of this slut.”

Removing Jesses’ legs from my shoulders and then using her knees to stand, I leaned in for a kiss, Letting Jesse taste herself on my face, before rising to take her other arm and help her to her feet.

Brian moved the chair out of the way, making room for Jesse to kneel and spread her legs for him, as he knelt behind her stroking his cock, and I stood in front of her stroking mine.

Jesse reached for my cock and pulled me closer. Looking back at Brian she instructed. “Slowly, and at the same time please. I want to taste his pre-cum.” while squeezing me from the base of my cock to make another drop appear at the tip.

She leaned her face to the drop and licked as while Brian moved in behind her. He pressed the head of his cock against her wet, puffy, lips while she licked the tip of my cock. Looking back she told Brian. “This slow.” Then proceed to wrap just her lips around the head of my cock and stop.

Her lips were incredibly warm and soft. With one hand on the base of my cock and one hand on the floor Jesse began to slip her tongue around the head of my cock and begin to coax another drop onto her tongue.

Slowly she started sucking harder while twirling her tongue she began drawing me in.

Her mouth was hot and moist as I stood watching her boyfriend start to fuck her. Glancing down I saw she was looking up at me and knew instantly that she liked having me watch her getting fucked while she sucked my cock.

I Reached down and gathered all her hair in my hands. Pulling it taut I then carefully began to spread it out on her back. “I want to watch it get soaked.” I tell her when I stand up and take her face in my hands again.

She began to take me in and I looked up to see Brian watching me with his girlfriends’ mouth around my cock, about halfway down the shaft, and my hands holding her head. I grinned and said “We should start fucking her now.” I began to push her head away, withdrawing from her mouth until I was just touching lips.

Brian got it immediately and slowly withdrew as well. Looking him in the eye we then, just as slowly as the first time, slid our cocks back inside, just as far as we were before and then a little further before slowly drawing back out.

On the next stroke in we went all the way and buried ourselves. We did it as slowly as the other two times and I looked into Jesses’ eyes as her boyfriend and I filled her. I felt her tongue stretching out as I entered the back of her throat and pushed her face against my stomach, my balls against her chin and her nose just pressing into me.

I felt her hot saliva drip down my balls when she opened her mouth wide and shook her head against me, driving me even deeper. Finally, she closed her mouth and began to swallow, the vibrations of her moan adding another dimension to what was happening to my cock.

The feeling was incredible. My cock was wrapped in waves and vibrations until she slowed and stuck out her tongue, licking my balls before slowly begin to push me away.

“I am ready now.” She looked behind at Brian, still buried inside her. “Let me get him in before you start fucking.”

He nodded and held her hips in his hands while the front of his, I am sure, felt the heat of her spanking still radiating from her glowing cheeks.

She took my cock in her mouth again, sliding me deep inside before stopping. I watched as Brian drew out and slid back in quickly, driving her face into my stomach and balls with an audible smack.

Jesse moaned against me when I went all the way into her throat and then back out a bit as Brian withdrew for another stroke.

I held myself against her with my hands on her head before I released her and just watched, feeling the heat of her mouth and action of her throat.

September 2018
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