older guy/younger girl
My name is Scott and those of you who have read my previous stories know that things have gone pretty well for me in my life for the past year or so. I encourage everyone to read my prior stories for the details, but I will give you a recap of things.
Just over one year ago, I took my assistant, Anne, on her first business trip. She was just a few months past graduating college but had worked for me in one capacity or another for over four years. Despite our age difference (I’m 15 years her senior), race difference (I’m black, she’s white) and other barriers (namely my wife and kids and her live-in boyfriend); our personalities immediately clicked and over the years we developed a very close relationship.
It just so happened that during the same time that I was getting closer and closer to Anne, my sex life with my wife was significantly diminishing. The quality was still great but the quantity was getting less and less. Having two small children and both parents working will impact anyone’s sex life, but still when you go from getting some three or four times per week to maybe once a week; that’s a pretty steep decline, especially for someone like me.
You see, my wife likes sex, but I absolutely love sex. Always have and God-willing always will. What can I say, I love pussy. My wife once called me a sex addict because of my strong desire. I’ve thought about it and the only reason I wouldn’t call myself an addict is because I’ve never allowed sex to interfere with my everyday living. This may sound somewhat hypocritical, but sex has never caused me to neglect my responsibilities, professionally or personally.
So when my sex life with started to diminish I needed something to fill the void. Masturbation, strip clubs, erotic reading and writing all helped as did some extracurricular activities with various women when I went on business trips.
Everything was cool until Anne and I started getting closer. I’m a sucker for a beautiful woman. Black, White, Asian, Hispanic I don’t care. Hot is hot and Anne is definitely hot. She’s 5’7″ roughly 125-130lbs with stunning model-like features and shoulder length blonde hair. And trust me; I know from experience that she’s a natural blonde. She was a high school athlete and kept a very well toned body throughout college. Her breasts are no larger than a B cup but her nipples are nothing short of exquisite. Her legs and ass are simply to die for. Long shapely legs that lead up to what I have repeatedly told her is one of the best looking ass I’ve ever seen. Perfectly shaped with just enough jiggle and shake as she walks. Many a times I’ve gotten rock hard just from watching her butt as she walked.
So obviously you can see why I would be attracted to someone like her. I don’t know how it started but our relationship quickly evolved into a very flirtatious one and there was nothing we couldn’t talk to each other about including our personal lives. After a while I couldn’t take it any more and realized I had to put a move on her. That’s when I came up with the idea of taking her with me on a business trip even though she really didn’t have any legitimate business reason for going.
It was one of the best decisions I’ve ever made and turned out better than my wildest dreams. The last night of our trip we spent in bed together kissing, fucking and sucking till the early morning. After that trip we initially agreed that it was probably for the best if was a one time event, but the more we worked together the more we realized that the sexual tension between us was unbearable. That led to us fucking like dogs in heat in my office during the company’s holiday party last December.
After that second encounter we realized it was useless to fight it and decided to hook up whenever a safe opportunity presented itself. Because of our situations, safe opportunities were few and far between but we did manage a repeat performance in the office one Saturday afternoon in March.
That was the last time we’ve actually fucked but she did surprise me with an incredible blowjob for my birthday in May. The exciting thing about that, besides the obvious, was that she did it in my office with about 15 members of my staff working just outside my door. I was dying to fuck her or at least return the favor and go down on her but Anne’s a screamer when she cums and we couldn’t risk anyone hearing. Truth be known, it took every bit of restraint I could muster not to scream out myself when I was cumming in her mouth that day.
But you know what they say, all good things must come to an end and the beginning of the end came for me and Anne not long after my birthday surprise.
About a week after that day, she came into my office and told me that she and her boyfriend had broken up. I guess it should not have come as any great surprise when you break-up with someone you’ve been cheating on for about a year but ironically enough the break-up resulted from him getting busted for cheating on her. The dumbass gave a girl he met the email address that he shared with Anne by mistake and she emailed him talking about how much fun she had with him and maybe next time when it’s not her time of the month she can do more that just give him a blowjob.
Despite having been together for nearly 5 years, Anne was not too upset about he break-up. It had turned into more of a relationship of convenience then love and how could she be upset with him doing something she’s been doing herself for the past year.
The problem was going to be her living arrangements. Anne and her boyfriend agreed to continue sharing their apartment for the two months it would take before they could break their lease; but with the cost of housing so high she would have to either find a roommate or look for a higher paying job. Not having Anne work for me was not a pleasant thought. Not only would I miss seeing her everyday but she was also one helluva assistant. After much discussion we decided she should cover both fronts just in case, look for a roommate and see what other job opportunities were out there.
With the future so uncertain, I knew I had to come up with another way to fuck Anne again and not have my wife get suspicious. With such a daily routine in my life, that was always much harder then you would think. Fortunately as luck would have it I was scheduled to attend an overnight training conference in the upcoming week. It was only an hour drive away but with it starting so early and me not being a morning person (for anything except fucking that is) I decided to stay at the hotel for the conference.
I was the only one from our company going and with Anne no longer having to explain or justify her whereabouts to anyone; it didn’t take much to convince her to meet me at the hotel. The plan was all set. The conference was on a Tuesday. Anne told everyone in the office she was taking Monday and Tuesday off to spend a long weekend visiting her Mother. I would work half a day and then drive down to check in the hotel early Monday afternoon.
Anne was already in the hotel bar when I arrived. She was finishing a drink while being ogled by a couple of drooling businessmen. I walked up, sat beside her and asked the cliché question, “Can I buy the lady another drink?”
“I don’t know what makes you think I’m a lady, but I could use another drink.” She replied with a seductive smile.
“Ok, if you’re no lady, then maybe I should have asked what’s a girl like you doing in a place like this.”
“Mr. Original, you’re not. But if you want to know the truth, I’m here waiting to meet a good-looking man to take me up to his room and fuck my brains out.”
“Well if that’s the case, why don’t we skip the drink and just head up to my room.”
“Sounds good to me. I haven’t gotten laid in over two months so I need to get fucked a whole lot more than I need another drink.”
Without another word, I took her by the hand and led her to the elevator. As soon as the elevator doors closed we both burst out laughing.
“That was so fucking funny. Did you see the look on those guys faces?”
“Serves them right. They were starring at me from the minute I walked in there. You know I don’t usually mind guys checking me out, but they were kinda creepy.”
“Well no need to fear my dear. Your knight in shining armor arrived just in time.”
“Oh yes, my hero. How on earth will I ever thank you?”
“Well for starters, a repeat performance of my birthday present will do nicely.”
“That was a rhetorical question, smartass. But play your cards right and you’ll be getting a lot more than that.”
“Yeah, yeah, promises, promises. So do you want to go out for dinner or just order room service?” I asked as we entered the room.
“Either is fine with me, but dinner can wait. I wasn’t lying. It really has been over two months since I got laid and you and I haven’t fucked in nearly six months. The only thing I want right now is your seven inches pounding my wet pussy.”
“Well that’s an offer I most certainly cannot refuse.”
We began kissing with the passion of newlyweds on their honeymoon. Falling on the bed with our lips and tongues not once separating from the other, the suddenness of my full erection surprised me. Reluctantly releasing our lip lock, I sat up to adjust the uncomfortable bulge in my pants.
She sighed and looked up at me with pure lust in her eyes and said something any guy would love to hear, “Scott, save the foreplay for later, get back down here and fuck the shit out of me.”
After stripping my clothes in record time, I yanked her shorts and thong off in one fell swoop exposing her beautiful glistening pussy. With her on her back I’m between her legs in the blink of an eye. I hear her gasp as I waste no time sinking my full seven inches deep into her hot tight hole. If it’s a fucking she wants then it’s a fucking she’s going to get.
I proceed to fuck her with reckless abandon and judging from the ooohs, mmms and yeahs, she was loving every minute of it. With her legs straight up in the air I was fucking her with the vigor of a twenty-year old and the expertise of a thirty-eight year old who’s learned a thing or two about fucking from over the years.
I didn’t want to disappoint her but the inevitable was quickly approaching for me as I continued pumping in and out her sweet pussy. Fortunately she beat me to the finish line and screamed out in orgasm for all the world and hotel to hear, “aaarrrgghhhhh Fuuuucccccckk yeahhhhh!” With her pussy clamping down on my dick, I joined her in pure ecstasy and shot what I hoped would be the first of many loads of cum deep inside her.
After taking a moment to regain our strength, Anne broke the silence, “I haven’t been with very many guys but I can’t imagine fucking could get any better than with you. I mean damn Scott, others have made me cum, but no one’s ever made me scream like you do.”
“Wow, you know how to stroke my ego just as well as you stroke my dick. I’m not one to brag but I do know a little something about fucking. I wish I could say that everyone I’ve ever been with had the same reaction as you. I just think like everything else about us, we just have an amazing chemistry that translates into amazing sex.”
“You may have a point about our chemistry, but don’t sell yourself short. Like I said, I haven’t been with a lot of guys, but I’ve been with enough to know good fucking; and the bottom line is you know how to fuck.”
“Well let’s see if I’ve still got it.” I said as I turned to kiss her and massage her ass.
“Slow your roll big fella. We have all night. You may be hard again, but let’s order something to eat and give my pussy a little time to recover.”
We ordered room service and showered together while waiting. In the shower the sexual tension between us increased as rapidly as the water temperature. My dick was firmly entrenched between her ass checks as she tilted her head back on my shoulder. With the water cascading over us I kissed her neck as I caressed and rubbed her breast, causing both nipples to harden. Just as I was about to enter her from behind we were interrupted by a knock on the door.
I reluctantly got out of the showered, quickly dried off, and tried my best to cover my precarious situation with a towel as I opened the room door. The server was a cute 20something female whom I would have normally flirted with under different circumstances. She quickly assessed the situation when she heard the shower still running and saw Anne’s shorts and thong on the floor. I gave her a big tip and she gave me a knowing grin as she left.
Over dinner we talked about everything except anything work related or involving her living situation. We wanted this time together to be completely free from our everyday troubles and worries. It was no surprise when the topic of conversation turned towards sex and sexual fantasies in particular.
“Is there anything sexual you haven’t done that you still want to do?” she asked.
“Do you mean with you?” I asked with a twinge of excitement.
“No… well, maybe, but that’s not what I meant. I was thinking more of your sexual fantasies in general. You know, threesomes, anal, that sort of thing.”
“Well I’ve been there; done that and pretty much everything else I’ve ever wanted to do.”
“You know, you’re starting to take all of the fun right out of this.” She said in a more serious tone.
“Ok, ok, there is one thing.”
“All right, now we’re getting somewhere. What is it?”
“I’ve always wanted to have sex in public. Not so much with people watching, but doing it some place that runs the risk of getting caught or overheard by someone. It’s something I’ve thought about since almost getting caught fooling around by my girlfriend’s parents in high school.”
“That’s a pretty good one.” She responded happily now that I was playing her little game. “I can’t see your wife going along with that, but I’m surprised you haven’t been with someone else willing to do it.”
“I’ve come close a couple times but never actually fucking in public.”
“Wow that must really be a major turn on for you. Just that fast you got another hard on. Men are so easily turned on.”
“Well I think sitting here talking about sex with a beautiful woman has more to do with my erection than just my fantasy. But don’t sit there trying to play all innocent, judging from your pointed nipples over there, I think it’s a safe bet to assume our conversation is having an effect on you as well.”
“You got me. Guilty as charged.”
“Ok your turn. What are your fantasies? And don’t leave anything out.”
“Well honestly, you’ve already fulfilled some of them. I mean sex with a black guy, sex with an older guy, sex with my boss. All of those were on the list before we hooked up. I just didn’t think they would all be fulfilled in one fell swoop.”
“Well I’m happy to oblige. What fantasies do you still have?”
“Ménage a trios for one and anal for another.”
“Well, well, well, my sweet little Annie’s a freak.” I said chuckling. “I should have known.”
“What’s so freaky about that?” she said defensively, “Plus you said you’ve already done both of those, so what does that say about you?”
“Oh I admit I’m as freaky as they come and proud of it. I’m just giving you a hard time. Look, I tell you what, let’s order dessert and when that cute little server comes back up, I’ll throw on my charm to get her to join us later so that you can live out one of your fantasies.”
“I hate to disappoint you but the threesome I want includes two dicks not two pussies.”
“Hey you just said ménage a trios. It’s not my fault the thought of you and another woman just happened to pop into my head.”
“Well pop it right out of your head. I don’t roll like that.”
“That’s what you say, but if I recall, you were turned on full throttle when a certain female stripper was giving you a lap dance last year. So don’t tell me the thought of being with another woman hasn’t crossed that pretty little mind of yours.”
“Damn, busted again. Ok, the thought has crossed my mind. I can see letting a girl go down on me and under the right circumstances I could possibly be persuaded to suck on a titty or two, but honestly I don’t think I could ever eat pussy myself.”
“Well fortunately for you, I don’t have any problem with that.” I said as I moved to the floor in front of her chair, parted her legs, and gently caressed her already wet pussy. “Wow, all of this talk really has affected you. Let me see if I can help you out.”
She undid her robe, slide down to the edge of her chair and gave me a magnificent view and unobstructed access to my most inviting target. Freshly trimmed with an inch wide strip of hair just above her clit, her hot moist pussy was an absolute thing of beauty.
The first lick made her shiver. The second lick elicited an ever so slight moan of approval and the third lick brought out the first of many to come oh yeses!
Eating pussy is truly meant to be savored and not rushed. I parted her engorged lips with my thumb and fore finger and then explored every part of her pussy with my tongue. The taste was exquisite and sweeter than any known berry. With each passing minute her juices increased in flow and I happily lapped up every drop.
I felt her hips rising upward ever so slightly as I continued my tongue fuck. I glanced up to see her with her eyes closed and mouth open in an O as she was massaging her breasts and pinching her nipples. Momentarily ignoring my own elevated state of arousal, I was determined to make this all about her. Sensing her readiness for me to take it to another level, I inserted one and then two fingers deep inside her. Her hip thrusts increased its pace to match my finger fuck and I went in for the kill by attacking her clit with my tongue.
Her reaction was just what I wanted, but the quickness of her climax came unexpectedly. Seemingly within seconds from me contacting her clit, her oh yeses became much more rapid and louder. Her hip thrusts turned into hip writhing and for the second time that day Anne screamed out in orgasm for the entire hotel to hear.
After she calmed down from her intense high, I realized that she had literally cum out of her robe. I picked up her nearly limp body and carried her to the bed. I looked down at her to admire her incredible naked beauty and sexiness until she broke me out of my trance.
“Don’t just stand there looking. Come down here and let me feel some more of that seven inch dick deep inside me.”
Never one to turn down such a request, I got on top of her and easily slid all seven inches inside her still very wet hot pussy. With my dick deep within her and neither of us moving, we begin kissing passionately. Without breaking the kiss, I begin a slow rhythmic pace of moving in and out her pussy. There’s something about kissing while fucking that takes the intimacy of the act up at least two or three notches.
We continued our rhythmic fuck for what seemed like a lifetime. Unlike our earlier raw passionate animalistic fucking, this time it was more of a controlled sensual fuck that I had normally reserved exclusively for my wife, who at the moment was the furthest person from my mind. Then it hit me like a ton of bricks. For the first time Anne and I weren’t simply fucking, we were making love.
I felt a momentary twinge of guilt about making love to a woman other than my wife, but the guilt was quickly replaced with intense pleasure and all I could think about was how incredibly nice it felt making love to her. Neither one of our orgasms matched the explosiveness as the one before, but on some level it was the best one we had ever experienced with each other.
“Is it just me or was that different?” She said after a long silence between us.
“No it’s not just you, I felt it too.” I replied.
“So what do we do now?” She asked.
“I don’t know, but we’re entering some pretty dangerous waters.”