Ever give a friend or acquaintance (not wife or girlfriend) a massage that led to sex

[randyman]

We used to go to a club in sheffield one night they had a male massues he was next to the jaccuzi which both myself and few others were in. To cut a long story short my wife had a massage and it wasn't long before he made her cum i have never heard her moan it extasy as much.

[doggone]

A few years after college, I was working for a time for a landscaping company, and would often frequent a local bar for a few beers after a long, sweaty day at work. There was an older woman I’d seen at the bar and talked to once in a while. I was probably 25 or 26, and she was probably around 45, plain looking and thin, but not athletic. I never thought of her in terms of hooking up, but must admit I’d had a fantasy about older women since I was a teen.

Anyway, one summer day after I’d had a few at the bar, she asked for some advice on her lawn. She offered me a couple beers if I could come to her house and give her some lawn care tips. I said sure, never one to turn down free beer. I followed her to home and found out she lived in a trailer park by a lake. I gave her some quick advice about her lawn, and we then went inside for that beer.

At some point she complained about her shoulders or neck aching, so I offered to rub them a little. Soon she was telling me how good it felt, so I told her I could do a much better job if she lay down. Her trailer was small, and there really wasn’t a separate bedroom, so the bed was just at one end of the living room area. She made a quick comment about how it would ONLY be a back rub. I said sure.

I slowly started rubbing her back and shoulders. Taking my time, I moved little by little down her back. Every time I’d move a little lower, I’d move back up to her shoulders and neck, then move further down her back again. When I got too close to her butt, she’d say, “that’s far enough”, or “hey now!” or something like that to let me know that was off limits.

After a while, I moved down to her feet and calves and massaged them through her jeans. Slowly I moved up her legs, one leg at a time. I kept explaining that if I released the tension in her legs, it would help her back and shoulders. She was starting to enjoy it more and more, so I suggested she take off her jeans. She laughed and said No Way - I was just trying to get her undressed. But I persisted, saying I’ve given plenty of women massages in all states of dress/undress. (Not true, at the time, but she didn’t need to know that!) Finally, she said it really would feel better, so she got up and removed her jeans. She also pulled off her shirt. Underneath, she didn’t have a bra on. Instead, she had a thin tube top.

I started rubbing her bare legs. Again I slowly started with her calves and inch by inch worked my way higher and higher up her legs. Every time I’d go to far up her thighs and approach her crotch or butt, she’d say something like “that’s far enough” or some comment about touching the wrong places. I’d say there was nothing further from my mind, just trying to give you a good massage. Eventually, I started rubbing the sides of her butt. I again told her how much tension women build up in their backsides, and how that affects the back and shoulders. Probably a bunch of BS, but it was working. Soon I was massaging her butt with no complaints, only moans. But still if I went to close to her crotch, she’d squirm and yell.

Next, I started telling her if she’d just remove her panties, the butt massage would be so much better. Same arguments about no sex or pussy touching from her, same “nothing is further from my mind” replies from me. Finally, she gave in and took off her panties. This time I started with long strokes, starting with her calves, and running my hands up over the backs of her thighs, then letting the heel of my palms push deeply into the sides of her butt, then back down to her feet. I stayed clear of her pussy at first. But with each stroke up her legs, I’d push her legs a little further apart, until I had a good view of her vagina. And each time I reached her butt, I’d push her butt cheeks outward, which started opening up her vagina giving me a real good view of her pussy and asshole, as well as a raging hard on. It didn’t take long, until I noticed her pussy lips starting to engorge and protrude. Soon, I could see wetness, as my hands worked their way up and down, up and down. Each time, I’d spread those butt cheeks and I see her pussy open and close. And she was moaning more and more, her breathing getting a little louder. I started getting closer and closer to her pussy. The first few times I brushed her pussy lips, she protested, to which I replied again, “nothing further from my mind,” but soon I was brushing her pussy lightly with no complaint. She was really getting wet now.

Suddenly, with a load moan, she pushed herself up on all fours with her knees apart and shoved her pussy against my hands. With one hand I started rubbing her clit, and the other I plunged a couple fingers as far into her as they could go. She was soaking wet!! I heard her say, “Oh my God, just fuck me!” She didn’t have to ask twice! I quickly pushed my pants down and buried my cock into her, and started fucking her doggie style. She became a wild woman, screaming “Faster, faster,” and “Harder! Fuck me harder!” Her face was only inches from an open window, so I’m sure everyone in the trailer park could hear! I was fucking her as fast and hard as I could and she was begging for more. Finally, she started yelling “Yes! Yes! I’m coming” and that was all I could take. I blew my load insider her as she was saying “Cum in me. I want to feel you hot cum in me!”

Finally, we both collapse to catch our breath. I stood up and said “Wow, I wasn’t expecting that”, although it was exactly what I was trying for. Believe it or not, she actually apologized to me for losing control and turning it sexual. Ha! No apology necessary, Ma’am! I said let me know when you need another massage. She answered with a big smile.

I never had a second time with her. A few weeks later I met my future wife, and I never had an encounter with that older woman again.

[jacoby]

My best female friend and I had been friends since we were both 4 years old. During our high school years we were very close and obviously attracted to one another but were always dating other people so nothing ever came of it. In college my house was really close to the bar district and she lived in an apartment complex that was a 5min drive away. So when we'd go out to those bars drinking she'd always stay the night in my bed with me because she could trust me. She would always borrow a t-shirt and boxers from me and put them on and remove her bra under my shirt I always slept in my boxer briefs and that was it which she was okay with because we never cuddled or touched. One night she changes in my stuff like always but doesn't take her bra off and when she's getting into bed tell me her neck, shoulders, and upper back were tense and hurting and asked if I would massage them for her I said yes. I start with her neck and work on that for awhile and she ask me to move to her shoulders I could tell I wasn't doing a very good job because of my t-shirt. She then asked if I thought I'd do as good a job on her shoulders as I did her neck if she took the shirt off. I said yes and she told me I had to promise to not get weird or try and grab her chest. I said okay. She has great DD breast and the she's wearing a lace bra. We've been doing this both sitting in my bed and get up on my knees telling her it's for "better leverage" but really it's to look down at her tits. I begin massaging her shoulders and she is enjoying it and after a bit I tell her I feel like her bra straps at in the way. So she takes the straps off her shoulders and takes her arms out I think she felt confident the bra was tight enough to stay. I begin to deeply and slowly massage her shoulders making her close her eyes and super relax. After a minute one side of her bra falls half way down exposing alot of her nipple and she doesn't notice 30 seconds later the other side does it as well. So I make sure I'm doing an awesome job so she's keeps her eyes shut and seeing her breast like that and massaging obviously my dick becomes rock hard and I'm only wearing my boxer briefs. As I said I'm up on my knees behind her and she becomes even more relaxed and leans back planning on leaning against me. When she does this the first thing her back runs into is my hard-on and she feels it making her spring forward and open her eyes while saying "omg you have a boner!" She then notices her bra and she says "I can see why you have a boner" and I reply saying "I started getting hard the second I saw you in that bra." She said "really" in a turned on tone of voice and then she says "well you got to see my tits so I think it's only fair I see your dick!" I thought was kidding but then she turns around looking at me and says "well." I know she's expecting me to just put it out of my underwear real quick and put it back when she turns back around. I'm still up on my knees and she sitting twisting her back to get a look so my cock under her face and above her tits area. Instead of giving her a quick flash I push my underwear down to my knees letting her know I don't want to put it up anytime soon. She then says "holy shit your dick is really fucking hard and looks big." I ask her what else she expected from me getting to see her the top half of her tits. She then says you didn't get to see them all and then turns around getting on her knees and takes her bra off and asking me if we were even now. I told not quite since I had been given her a massage for 20 minutes and with hesitation she begins stroking my cock and I start massaging her tits. I tell her I want to give her a full body massage and that those boxers would have to come off she says okay but tells me her thong is staying on. She takes the boxers off and what she calls a thong I call g-string and they are thing lace in the front matching her bra. She asked me if I want to start with the front of back and I instantly say back because she has a nice pawg ass, wide hips, and lucious thighs. I quickly do her back making my way to her hips and ass as fast as I can and I spend alot of time there. Stopping every once and awhile to jerk my cock real quick and she notices all the stopping I'm doing and ask why. I tell her I'm stopping to give myself a quick "massage" and she's replies saying massage her with it. So place it right on tops of her ass cheeks and I begin deeply massaging her hips with my hands on the outside of them in a rotating motion while grinding my cock on the top of her ass cheeks. Each time I massage the sides of her hips down its spreads her ass and cock goes deeper in between her cheeks until my cock is completely in between both checks and I'm just grinding away. Not long after that she pushes me away real fast pulls her g-string to one side arches her hips up and says "fuck me!" She's insanely wet and my cock slides inside her pussy so fast and deep it feels amazing and she says "holy fuck you're deep." I then begin fucking her and she loves to talk one of things I remember her saying is "omg if I knew your cock was this big we would have been doing this a long time ago!" Any we fuck in a couple more positions she cums and then want me to cum on her face and mouth and I obliged. We have been secret friends with benefits ever since and that was 10yrs ago. At the time I had a gf and she had a bf but that never stopped us from having secret rendezvous. I've been married now for 3 1/2 years and she's been married 2 years and we still fuck whenever we can. Our spouses think we have a brother sister relationship so it's pretty east for us.