[Request] Friends With Benefits

[lgnclark]

Over the past few years, I've had some really good experiences with fostering "friends with benefits" situations with a few women. I have tons of stories to share. I love the "fwb" situation because it cuts to the chase, and usually, both parties are quite committed to the common goal (ha). If handled just right, it can be great situation.

I'll start the ball rolling with an account, but I'm hoping to garner more responses from people with experience in similar situations.


The year after I graduated from college, I lived at home while finding a job/finding a place to live. While doing so, I spent time on craigslist looking for jobs and wound up exploring the personals section. Eventually, I got in touch with a girl around my age (I was 23 and she was 22). She lived about an hour away from me and had also moved home after college. We exchanged a few emails that contained pretty generic dialogue (discussing college life and future plans, interests, etc.) We got along well and exchanged numbers. This was around May/June.

After sporadically exchanging emails and texts, we agreed it'd be interesting to meet up at some point . Of course, in my mind, the possibility of a hookup was intriguing. She'd sent me a few pics, and her look was right up my alley--pretty, with a nice curvy body (I'm a sucker for ass and tits). The opportunity finally arose when I was spending the evening at a friend's apartment in the downtown area of my city.

She'd driven into the city with a few friends for the night and was enjoying the benefits the city had to offer, namely lively bars and clubs. At one point during the night, she texted me to let me know she was in the area and suggested the idea of meeting up. Of course, I was all for it. After exchanging texts for most of the night, we agreed to meet up by a nearby subway stop--she was with a group of friends, so the agreement was that I'd meet up with her and her friends, so as to avoid a sketchy situation (I was all for it). We did so, and when we met, she was wearing the same outfit she'd worn in a photo she'd sent me. It was a low cut, blue sundress that showed off more than a taste of her amazing rack. We hit it off well, chatting and walking around with her friends for twenty minutes or so, when we both realized we got along just fine. At that point, I suggested we take a cab back to my place and it was on from there.

Once at my place, we headed for my tv room, where we made some idle conversation with the tv on (I seem to recall watching/discussing Brett Favre). Inevitably, I leaned in to kiss her, and then we went after it. We made out ferociously for a few minutes, with my hands all over her hips and ass and tits. I was in the midst of unhooking her bra when she asked to go to my room. Naturally, I obliged.

We got to my room and immediately the dress came up over her head, and off. She stood there in her bra and panties--her curves fully exposed. Her bra came off first--she took care of that, and I stood behind her and slid her panties to the ground. I reached around and grabbed her tits, squeezing and pinching her nipples and kissing the back of her neck. We then stumbled to my bed where the kissing and exploring continued. My clothes disappeared soon, and I soon found my head between her legs. I lapped at her pussy and slid a finger inside her. By then she was dripping wet, and I proceeded to tease and prod and see how she responded. Her moans and gyrations kept me going.
At some point, she stopped me and drew me close to her--my stiff cock was dying to slide inside her. I began to slide slowly in and out of her, driving deeper inside of her with each thrust. She tilted her head back and welcomed me inside her pussy. From then on, it became a blur--she rode me, I bent her over and took her from behind...we went at it hard. Her tits bounced, her ass shook. Finally, I pulled out and exploded all over her tits. That was the end of the first night, but we had many more nights to come after that...

[ai conomio]

This didn't happen until later in life, after the term "Friends with Benefits" was coined. It was after my divorce. At the time I lived in a medium sized city in the Midwest (United States), and there just wasn't that much opportunity for a middle-aged guy to meet women. For one thing, it was a fairly tight knit blue collar community, and I had a graduate degree, a professional job and I wasn't a native. The locals already had their friends and relatives and cliques. Another thing is I don't hang out at bars. The smoke kills me. It was only a couple years ago that they outlawed smoking in bars in that state.

Like a lot of people, I decided to give the online dating sites a try. Most of those sites suck big time. One even admits the male to female ratio of members is 10 to 1. It didn't take too long to exhaust the possibilities. I did get together with a few, usually once or twice at most, but there was never any reason to continue seeing them. One chick listed herself as having a "regular" figure, but in fact she was so overweight that she had bat wings! You know, when the flab hangs down from the arms. I should say that I weighed about ten pounds more than I did in high school 35 years earlier. Heh, I have a high metabolism.

Now I actually like big women (not that one!) when they try to look nice, or at least make an effort to be sexy, so I never rule out anything when I meet someone new. That turned out to be a good strategy because I did eventually meet a young lady, 15 years younger than me anyway, who liked sex as much as me, and was satisfied with just a FWB relationship. Carol was shorter than me by quite a bit, but heavier. She was significantly overweight, but I have no ability to guess weights, so I can’t say what she weighed. I have no idea what size bra she wore, her tits were just big.

How is it that everyone here seems to know the cup size and measurements of all women they’ve ever fucked? I don’t believe what they say about their own cocks either, so I’m not going to tell you about mine. I have no idea how it compares to anyone else’s, and I don’t see how it has any relevance to the story anyway.

I have to stop now, but I am not going to ask “do you want to hear more?” half way through the story, and make you beg me to post more. I’ll finish this later, but maybe not until next week as I’m getting ready to go camping for a few days, and I have a lot of things to do first. See for yourself, this is her, you figure out how big her tits are:

[ai conomio]

Warning: I'm a recovering analytic; it's a 22 step program.

I'm merely asking, how in the heck can anyone actually recall, accurately, the breast size of someone they bagged once or twice, 20 years ago? They are like fishing stories, the part of the story we are so proud of seems to get embellished every time we retell the story! As for penises, look at pictures here or on Flickr. To really make comparisons, you have to stand in front of a mirror and look at yourself and the computer at the same time, and take into account the difference in scale. So in that context, it seems to me that the only way you can really compare your erection to another accurately, and have any clue at all how your size compares to everyone else's, is to compare penises side by side. So... what was your sample size? I'm still collecting data myself! I take descriptions of body part sizes waaaay more seriously from members who contribute stories about their swinging adventures. They are more likely to have collected enough data to actually know body parts well enough to describe them accurately. I chuckle though, when a statement that one's penis is above average size appears in the first paragraph of the story. Same with detailed descriptions of women's figures. To me, that comes off like high schoolers bragging to each other about how much experience they have. Sure, we all do that to some extent, me too. My claim to not know anything about penis or tit sizes was meant to be a self-deprecating way to admit I don't have much experience. That's all.

[ai conomio]

Recognize my avatar?

[ai conomio]

Back to finish my story: After the requisite online back and forth, we set a date for lunch at a local place. It was a little awkward; she talked non-stop, mostly out of nervousness I think. We set another date to go to a concert, a community symphony. It was a nice concert, as far as a community symphony concerts go, but it was still very awkward between us. After the concert we decided to look for a place to get a cup of coffee. She didn’t like bars either, but that city sucks for places to go other than bars. The place actually has more bars per capita than any other city in the state; tells you what kind of place it is. We gave up after finding three places closed, one for good even, so I took her home. By then it was getting extremely awkward, and late, and we both had to work the next morning. She had a roommate, so we just kissed goodbye in the car. Nothing to write home about, but it became clear to both of us that it wasn't going to be awkward anymore. The next day I invited her over to my place for dinner, and things went much smoother right away, starting with a long deep kiss. I grilled some meat, opened a bottle of red wine, and put on some good music. I have about 600 CDs, the ex got the other half. After eating, we sat down in the front room to talk and listen to music, but fairly soon after we were seeing how deep we could bury our tongues down each other's throat. I don't think it was even five minutes later that I’m releasing her tits from captivity, and they were bigguns, and she’s running her hands all over me. She wasn’t holding back, nor was I. We had already eaten dinner after all, this was dessert. It could not have been 5 more minutes and I had her skirt, pantyhose and panties off. There she was, legs splayed wide open, with me on the floor in front of her eating her pussy like I was starved. It had been a while for me, and I found out later, her too. As I’m sucking her lips in and out of my mouth while alternating licking her clit, I look up at her and see that she’s totally gone, oblivious to everything. She looked like she was in a trance, moaning loader and loader, and it didn't take long for results. Actually, she came faster than any other woman I had ever eaten before then. The moment she came, her eyes actually rolled back to where I could only see the whites. I always thought that was just a figure of speech. No, it isn’t.

She and I got together many times over the next couple years. It was off for a couple times when she found boyfriends, but back on again when those relationships didn't work out. For a brief period I was actually seeing someone else and Carol at the same time. Never had sex with both in the same day, but in the same week a few times. Neither knew of the other of course. One very fun part of our relationship was the introduction of photography. I had never found anyone that wanted to be photographed, and she had never even done any casusal nude posing, much less anything more explicit. I was able to gradually get her started by taking it slowly with breasts only and artistic style poses. I had previoiusly done some nude self-portraits; fully nude, but no erections or anything that explicit. My intent was to use them on and "Adult" dating site. Anyway, after seeing the photos I had taken of her, and those I had taken of myself earlier, she started to get a lot more comfortable with it, and eventually I was able to take pictures of everything. Shortly before she moved out of town for a job she found another boyfriend, and so at that time our relationship was on hold again. She moved back about a year later, but she married the guy, and so it was then that our FWB relationship ended for good. I miss the photo sessions, but I still have the pics! I promised her of course that I'd never show pictures of her that anyone would recognize, and I haven't, and never will. I have however, posted some good shots on Flickr -- all unrecognizanble - no face, beauty marks, jewelry, identifiable backgrounds... Here are a couple more pictures of her for your viewing pleasure: The first is a shot of what I was looking at that first time I got her undressed and went on her. The second shot is one of our attemps at erotic photography. Hope you enjoy.

[freee]

Long ago I wanted to publish this story, but do not knew where. I hope this is the right place.
This is a true story that happened a few years ago at a special moment in my life. I will tell it as I remember, some references have been omitted or altered slightly to address cultural differences. Initially I wrote this text in Spanish, so some details may be lost in translation. I split it into two parts for easy reading:

Intro: The first approach
Vicki is one of my dearest friends for over 10 years. When we met we had a feeling that suggested that something might happen between us, but at that time I was in love with another girl and I preferred not to advance in search for a relationship with Vicki. Yet she was present during those times as a counselor and loyal friend. Years later I had the most important relationship in my life and during that time I could see little Vicki. When the relationship ended, I fell into a depression which took me out. It was at this time when almost by accident I came to meet with Vicki. She also had just ended a relationship, but not so as traumatic as mine. After all, she was accustomed to short engagements, because I met at least 4 of their boyfriends in a couple of years. To rediscover she could not recognize myself in the state in which I was. A merry-go-lucky guy who had known was now a dark and decadent shadow, she was 28 years old at the time and I 27. We talked for a long time and plan to meet the following week.

We both were preparing exams and met in my house to read and study in peace, at night. We had dinner and then went upstairs to the balcony to smoke a while as we rested.
As we watched the moon I hugged her from behind. We continued whispering. She showed no change, but I felt a very warm feeling being her body so close to mine. In the position we were in, I looked down and saw her cleavage. I could clearly see the depression between her small breasts. I commented that the view was beautiful from there, waiting for her response. she only said "they are very small". I told her that anyway they looked beautiful, and then almost without thinking, my hands slid over her breasts and fully grasped. Vicki looked surprised and tried to withdraw my hands. However the resistance offered was not enough and soon managed to reposition hands over her soft tits.
I asked him to let me have them in my hands for a few minutes. She said she did not like, so I said, "Just tell me STOP and I let you go" she repeated that she did not like, and I again said "Just tell me STOP." She smiled slightly but said nothing. Taking confidence, I lifted her blouse to expose her bra, this does not seem to mind particularly. But when I tried to unzip this last obstacle, she showed resistance. With some caresses and kisses, I achieved my mission and I was finally able to expose both breasts.
The darkness of the night prevented me from observing its details but by touch I could perceive these two small mountains and her nipples were hard by contact with the outdoors. At that moment I felt I was doing something wrong and let her go repented. I asked her to excuse me, I did not knew why I have done it. She said nothing, but did not look upset. We sat on a bench. I tried to change the subject, but I was not able. I explained her that the reason for my inappropriate advances was because I had not been with a girl since I broke up with my ex, so I was accumulating a lot of sexual frustration. She understood me and told me not to worry about it.
The rest of the night was very strange and confusing, we return to our respective reading studies, but I could not stop thinking about what had happened. Before she left I returned to exscuse me for my bad behavior. And that's when she told me that my problem was the lack of sex. I asked how I could help it, and she said she could help me. She told me she did not want to see me in such a pathetic state, and that if she could help, even when sleeping with me, she would. But nothing would happen that night, as she had to leave.

The Sweet Night part 1
A few days later I called to remind her offer and meet again.
The appointed night came a week after the previous one. We went with two friends, drank a few drinks, listen to music and play pool. After a few hours we said goodbye to my two friends and headed to my house. My family was sleeping and there was a great silence in the house.
We headed to my room with some drinks. We lay together in bed, we began to gently caress. It was not long before I removed her blouse. Then I tried to remove her bra, but like the previous time, she used her arms to resist leaving their breasts exposed. I slowly began to persuade her to separate her arms. I could unfasten her bra and slip it over as she covered her breasts with her hands. With a new session of kissing and fondling I got removed one of her hands.
This time I could clearly see her nipple, since the last time darkness had prevented me from seeing the details. The nipple was pink and stood hard easily. I stroked the outline around with my fingers and started to suck it. then I repeated the process with the other breast. Although I had already discovered one of her nipples, she still refused to show me the other, she laughed, as she enjoyed this game. When finally both nipples were exposed at the same time, I could not help but be transfixed by the image. Vicki completely topless in front of me, with her small, lovely breasts within my reach!
I said she looked more beautiful than I had been able to appreciate the night before. Then I asked her if she still wanted to continue. She does not looked convinced, so I lay beside her and began a separate unrelated conversation. During this talk she remained topless, as if it had been used to and feel very comfortable as well. Suddenly I felt a great desire to see her completely naked, and my hands slid the buttons of her jeans. however she opposed with great resistance. I tried to convince her with kisses and caresses, just as I did to remove her bra, but it did not work this time.
I asked if she would undress if I do it first and she said yes. then I started to take my clothes off. My shirt first, then the middle and trousers. When I was off to my boxers, I felt a concern, because I thought that after getting completely naked she would not meet his end of the bargain and I would be embarrassed.
Sometimes I enjoyed CFNM, but on this occasion I would have felt humiliated, so I stopped. I proposed Vicki to undress both simultaneously. She thought a moment and then agreed, but on the condition that the light were off. So we did and in a few seconds I was completely naked in the shadows. I heard the sound of slipping clothes and felt movement beside me. When she stopped, I ran my hand slowly toward the body of Vicki. I felt her skin. I ran my hands over her breasts and down direction, circled her waist. for some reason expected to feel the touch of her panties ... but I did not. I could feel Vicki totaly naked body next to mine.
Then she leaned over me and I could feel the heat of her skin over me.
She pushed her thigh against my cock and she could feel that I had also fulfilled my end of the bargain. She began to gently stroking, rubbing the skin of her breasts and legs against me. At that time my penis was completely hardened. I felt the need to see it in all its glory and my hand went into the lamp switch. When I turned it on, for the first time had the image of Vicki completely naked and on top of me. She was surprised and felt very embarrassed. She tried to cover but realized it would be in vain. My gaze fixed on her pubis, which was completely shaved. Her legs slightly apart left hovering pink lips of her pussy.
I could see she was wet and I could not resist caressing it with my fingertips. She watched my erect member, this time seemed interested in what she was seeing. Stimulation of my fingers made her start to moan. I continued doing that until I thought she was going to orgasm. Her fluids were in my hand now. At that point I stopped. I did not knew if we were going to continue or if it would end there. She looked at me confused and for a few minutes both were silent. I looked at my penis and I noticed that the erection began to subside.
We lay back. We started a conversation about totaly unrelated things. After a few minutes it seemed there we would not have sex, but none of us tried to get dressed and get out of bed. I think that soon all would be over, I leaned over her to look in more detail throughout her body. Her initial embarrassment seemed to have disappeared completely as it allowed me to observe every inch of her skin. But at one point I wanted to separate her legs to better see her vagina, and she resisted. I slowly began to caress her thighs and pubis, until her strength gave way.
This time I could saw in all its glory her parted lips. It really was a beautiful view. Then I masturbated her for several minutes and her body was writhing in pleasure, until at one point seemed to climax and I stopped. I went to lie down beside her.
I told her what I had done had been fun and that if she wanted could finish now. But she showed decision. She took my cock in her hand and began to rub it up and down. Then she put it in her mouth and began to lick in circles around the penis. I could not believe it, Now my cock were completely inside her mouth!!! Soon I got my state of high hardness and Vicki positioned over me again. I stare at my penis as she took it into her little pink box. My world was shocked and filled with heat to feel Vicki, my great best friend, surrounding me completely!!!

To be continued.

[captaintrips]

Originally Posted by freee

... I stare at my penis as she took it into her little pink box. My world was shocked and filled with heat to feel Vicki, my great best friend, surrounding me completely!!![/COLOR]

To be continued.

Fuck me that's a hot story. All the better for your quirky English. Do not have a second thought about i. I can't wait for Pt.2

There is something special about finally getting together with someone you have know for years and both have waited patiently for the right opportunity.

[freee]

This is the second and final part. I will tell it as I remember, some references have been omitted or altered slightly to address cultural differences. Initially I wrote this text in Spanish, so some details may be lost in translation:

The Sweet Night part 2
Vicky moved sensually over me. Undoubtedly she knew her way around very well. I felt like I was in a movie, I could not believe my longtime friend was having sex with me. All that feeling coupled with the fact that I did not have sex for a while, caused I did not last long. When she noticed that I was coming, she turned away from me, but not enough to avoid keep part of my semen inside her. She finished me gently by hand.
I took some TP to wipe, as she leaned back on the bed. Neither knew what to say, so we just laughed for a while.
It was about 3:00 am and Vicki said she was sleepy. I patted her on the back and buttocks. I did not feel sleepy and did not wanted it to be over yet. I tried to talk to her, while I replenished my energies waiting for a second sex session. But she was very tired and ready to sleep as she was, without wearing any clothes.

I found it very sweet to see Vicky completely naked lying face down beside me. I took my cell phone slowly and activated the silent mode. I started to take some pictures of her ass. Although I did not let out any sound she heard the movement and opened her eyes. When she saw me, I said her that I wanted to keep a token of this night and that she seemed very beautiful. She protested, but turned in the same position as before. I activated the option of video and started filming. I stroked her beautiful ass and back and asked her to swivel to see her breasts. She agreed, smiling, as if to comply obligatorily with the whim of a child. I slid the cell phone over her small breast while caressing and finally drove it downstairs with the intention of recording her adorable pussy. She had her legs together and I tried to separate them slowly, but then she stopped me and told me that was enough. I did not want to tempt my fate and stop the recording. I continued stroking and kissing every part of her body.
It had been almost an hour since I had ejaculated and she had barely slept. I asked her to have sex one last time so I could also sleep. Apparently she thought that the only way to stop my "annoying" caresses and kisses was by meeting my demands.
She asked me how I wanted to do it and I asked her to do the 69 position, because it was my favorite with my previous girlfriend. She blushed because it was still embarrassing for her that I looked at her fully spread. She positioned herself above me placing her mouth against my penis and her ass close to my face, though not completely against me. She said “no lick”, because she wanted to finish me quickly. She started working on my dick with her mouth and hands. Unlike the previous occasion, this time the erection delayed because I was beginning to feel tired too. I slowly positioned her with her ass on my face. Then I had her pussy touching my lips and I could also see for the first time her anus!
Like the rest of her body, her asshole looked delicate. It occurred to me that probably she had never given it to her boyfriends, but never asked her. The vision of Vicki`s most intimate parts made my penis harden again. But once more I lasted little, my level of excitement was overwhelming with so much beauty.
This time Vicki took the job of cleaning my cum, and she did so with an almost maternal dedication that made me feel ashamed. She said she had accomplished and hoped that I was satisfied to finally sleep.
Indeed it was, and we slept both totally naked covered by a single sheet. At times I held her pinned to her back resting my penis on her buttocks.

I woke up with the feeling of having a big dream but the beautiful view of her ass made me realize that everything had really happened. I picked up the phone and took more photos of her ass. When she woke up we were frolicking naked in bed. Now she covered her entire body with the sheet, as if embarrassed again that I could see her naked. She got up to pee and took her clothes to dress, because my family could see her if she left my room to the bathroom. But I convinced her that instead of dressing completely, that just wear my sport jersey which covered her to her knees. When she returned from the bathroom I hugged her and began to fondle her breasts through the jersey, it was very sexy to see her wearing only it.
But I would rather see her completely naked, so again I'd removed the jersey. This time she seemed to have gotten used to my habit of having her fully naked so she did not resist. She announced that she would leave in an hour, so I asked her to let me take more pics before getting dressed, to remember this ocassion when she was away. She agreed after made me swear that no one would see them. I took some close up of her nipples and her pussy. After a little prodding I managed to take a full frontal shot. I regret that the quality of my cell camera back then was very crappy.
While she dressed I went to make breakfast. We talked about several things while drinking coffee and almost not referring to what had happened at night. It was as if we had suddenly returned to the relationship we had before sex. Obviously nothing sentimental would happen between us.

The moment she was about to leave approached and then, blushing, I asked something else.
I told that her oral sex technique was very good, better than my ex girlfriend and I wished so much before she leaves, to please me again.
She protested that she was running late because she had chores to do at home. I said if she did it once again I could take it as my birthday present. She felt she could not deny it, so she accepted. I lay down on my bed and she started undressing me.
She put my clothes on a chair once at a time.
I remained only wearing a shirt. I asked her to undress as well but she said no, that was her only condition. She leaned over my genitals and began to stroke the penis. I took the sheet and covered my balls, because sometimes it embarrasses me that a girl could see them, and it was now brighter than the night before, so leaving me more exposed. However she quickly pulled back the sheet and said they were from her. Smiling I covered with my hands, but she also put those away saying it was her turn to see everything from me. Then she kissed me fondly in my scrotum. This stimulation made me harden quickly.
Vicki put her lips on my erect cock and started working on it. Giving circles with her tongue and held there for about 10 minutes. This time I lasted longer and I remember it to this day as one of my best orgasms. I ran threw my whole load on the bed while she continued stroking me with her hands a few minutes to extract the last drop. As she had done at night, she cleaned me gently and then helped me to dress.
We clean up a bit and I accompany her to the bus stop. All the way we were laughing recalling the great night we had passed. She said she liked see me smile again and hoped having "helped me" which was absolutely true.
We saw each other again in the following weeks, in her home or elsewhere, but we never had sex anymore. She got a boyfriend the next month and then we hardly met. A few times we talked of what happened. A few years later she asked me about the pictures we took that night, and after seeing them she complained for having gained weight since then (although she still looked splendid). She asked me if anyone else had seen it and I confessed that I had shown it to some friends. This does not seemed to bother her as she felt that it was not her in those pictures.

Remembering this story make me want to see her again. I know now she has a different boyfriend, so the chances are that nothing sexual happen again. But I still want to see this great friend who gave me her body to help me at a bad time.

The end

[GRITS]

READ our posts on - OPEN-Sharing your wife.. thread... thats all we have, friends w/ benifits.... my last post was from thurs. romp w/ friend.