Current location: Texas
Highest education received: Some college (currently in college)
Occupation: Tech support
Relationship status: Engaged
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10 (8 intercourse, 2 oral only)
How many hookup stories have you here posted before? 5 so far
Friends In Need
How long ago did this hookup happen? Late April 2012
How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Friends-with-benefits
Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? She is white with long straight blonde hair, average height, very plump, and very cute. I’m going to call her Ellie for the sake of this and future stories. We had first met back in the fall of 2009 shortly after I had come home from my deployment to Iraq with the army national guard. She was the best friend of one of my ex-wife’s (we were married at the time) friends whom she had met while I was deployed. As a couple, my ex-wife and I had gotten to know Ellie reasonably well, but the times we got together were too few and far between to say we were close friends, especially after she moved to a different city that was about a two-hour drive away.
Ellie and I were not exactly physically attracted to each other. We appreciated each other’s figures, but she was not really my type and I wasn’t hers either. However, we did have a sexual attraction that is difficult to explain. We never said or did anything about it when I was still with my ex-wife, but we both could definitely tell it was there.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? About three months after my ex-wife and I separated (we were not officially divorced until about a year later), Ellie sent me a text telling me that she was hurting from a rough break-up and asking for advice on dealing with the loneliness. We had not talked much at all since my ex and I had separated and hadn’t seen each other since before then. I talked with her about some of the ways I had been coping with my separation and gave her as much encouragement as I could honestly give.
Our conversation eventually worked its way to the topic of sex. She said that he had lost interest in having sex with her several months ago, and that was one of the primary reasons he broke up with her. I told her that I was so devastated when my ex and I separated that I had totally lost interest in having sex altogether, but now my sex drive was beginning to reassert itself with a vengeance. After that, she confessed that she has wanted to wanted to fuck me for some time now, but wasn’t willing to do anything because I was married even though she knew we were in an open relationship. I likewise confessed that I have wanted to fuck her too, but I was worried that things might get weird with my wife and our friendship. Our conversation quickly went down the path of detailed dirty fantasies we’ve had about each other, and before we knew it, we were seriously discussing the possibility of being friends-with-benefits and planning our first hookup.
She was already planning on a trip into town, and we tried planning a hookup around that. Unfortunately, we determined that we wouldn’t have sufficient time or privacy to really fuck, but we would be able to spend some time together and maybe discreetly fool around a bit. However, we were able to make plans to meet the next day at a hotel halfway between where we both live in the early afternoon for several uninterrupted hours. We excitedly made hotel reservations for the day and then spent the next few days getting each other worked up by spending a few hours each evening on skype getting naked and talking dirty over webcam.
What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? She came to town as planned to visit some friends and came over to the apartment I was living in at the time to spend a few hours with me and my roommate (we’ve both been friends with her for a few years now, but never really close friends). We didn’t want him to know what we were up to because he works with my ex and were worried about any possible complications that may come from her finding out. We started watching tv together, but, fortunately for us, he soon decided to go upstairs and take a nap.
Before we knew it, Ellie and I started making out and groping each other on the couch. She looked into my eyes with a hungry stare while she unzipped my pants and pulled out my cock. I stifled my moans as best as I could while she showed off her expert deepthroating skills. The look she gave me with her big blue eyes while sucking my cock was absolutely exquisite. I even pulled out my phone and took a few pictures (something I’ve never done before with a partner). I let her know that I was getting close to cumming, and she told me she would have to stop since she doesn’t swallow and she couldn’t risk getting semen on her clothes or in her hair. I was disappointed, but she assured me that she would make it up to me the next day. We made out for a little while longer, and then she left.
The next day, I was full of anticipation as I went about my morning routine, bought a box of condoms, and then drove out to the hotel. I arrived first and checked in, and she arrived soon after. Neither of us had eaten, so we grabbed a quick bite to eat first. Then we went back to the room, stripped down to our underwear, and laid down on the bed. We relaxed for a bit and made casual conversation, just taking in the moment and letting things progress naturally. When we reached a natural pause, our eyes met and we leaned in for a kiss.
That kiss set our bodies in motion. Soon we were rubbing, groping, and tearing each other’s underwear off. I kissed, licked, and sucked my way down the front of her body and then began to work my tongue in, on, and around her labia. She was squirming and moaning by the time my tongue found its way to her clit. She gasped, froze, and then started thrashing as she had her first orgasm of the day.
She finally caught enough breath to find the words, “Fuck me now!” I quickly slipped on a condom and plunged my cock into her hot and wet cunt. I could hardly believe how amazingly warm she felt. My dick felt like it was going to melt into her like a warm stick of butter. She came again almost immediately from the sheer sensation of being penetrated, and I started eagerly fucking her hard. It wasn’t too long before I felt the familiar sensation in my balls that told me I was about to pass the point of no return. I told her I was about to cum, and in the sexiest voice I’ve ever heard up to this point in my life she told me, “then do it.” I felt fireworks going off throughout my body as my climax reached its crescendo. Pure ecstasy overtook my senses. Every nerve in my body was vibrating with pure bliss as I slowly came down from such an amazingly hot brain-melting orgasm.
She looked into my eyes and smiled, looking very satisfied herself. Then made a comment about how warm it felt inside her. What was left of my mind began to panic instantly. Did the condom break? I knew she wasn’t on birth control. Did I just fill her fertile vagina with copious amounts of baby-making sperm? I quickly pulled my penis out of her, being sure to hold on to the base of the condom, and saw with great relief that it was indeed intact…and very, very full. She gazed wide-eyed and gasped at seeing what looked more like a cum-filled water balloon than anything else hanging down from my dick. It had definitely been a while since I had had sex or even masturbated, and this moment certainly demonstrated that fact. We had a good laugh about it, and then I disposed of the condom and slipped back into bed.
We cuddled and talked and reflected together about what we had just done. I was amazed at how comfortable and natural it felt to have sex with her, and she shared similar revelations about having sex with me. Taking stock of our feelings, we knew that we were definitely closer to each other emotionally now because of the sex. Still, there was no romantic spark between us. We still felt very much like friends, not lovers.
After a while, we began to feel ready for another round. This time we decided to go at it doggy-style. I slipped on another condom while she got on her hands and knees. I took several moment to admire her deliciously plump ass before guiding my cock into her from behind. Her whole body reacted with an intense wave of pleasure and her mouth opened silently, followed a second later with a gasp and moan. “It’s so deep,” she said three times over. I remembered that she had told me she’s used to fucking chubbier men so she wouldn’t be so self-conscious about her weight. I then realized that chubbier men couldn’t likely fuck her as deeply in this position as I could because their stomachs would get in the way of her ass. Encouraged by this, I grabbed onto her hips and thrust harder, which was satisfyingly met with even louder exclamations. I reached forward and grabbed her hair, which absolutely drove her wild. She bucked her hips back wildly and let out a scream of unbridled ecstasy. That familiar feeling in my scrotum returned, and I plunged my penis as deeply as I could into her as my body was once again enveloped in the rapture of intense orgasm.
We both slumped down to the floor panting, drenched in sweat, and in a state of total bliss. We stayed like that until we realized it was getting close to time for us to part ways. She had a friend coming to visit that evening and needed to get home soon. We got dressed, kissed several times, and went our separate ways home.
Did you have an orgasm? Did your partner(s)? I had two orgasms and she had several more.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I wore a condom for each time we had intercourse.
What were your REASONS for having this hookup? We were both feeling lonely and having incredibly strong sexual urges toward each other.
Were alcohol or drugs involved? If so, how much? Neither drugs nor alcohol were involved.
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I drove home feeling more relaxed than I had ever felt before in my entire life. I spent the rest of the day basking in the afterglow of the amazing sex I had just had.
Ellie ended up telling her friend (I’ll call her S) that came to visit what happened. This happened to be the same friend that my ex-wife had gotten to know while I was deployed to Iraq, so S knew me reasonably well. S was a little surprised that Ellie and I had hooked up, but was cautiously in favor of the whole relationship. She was a little concerned that our emotions might get out of control and the relationship might go south, but for the time being she was glad that her friends were having fun getting their rocks off together.
We were both very enthusiastic about how things were going, and we were looking forward to having many more incredible sexual experiences together. We continued to have amazingly great casual sex for the next three months, but by that time we needed to bring the benefits to an end because I was starting to date this wonderful woman that she introduced me to (and to whom I am now engaged) and she wanted to start dating again as well. We had a brief falling out shortly afterward because of mixed signals about possibly reinstating our benefits, but we worked through it and are still friends today.
To whom did you talk about the hookup? How did they react? I have talked to several of my newer friends about her, but I have never given a detailed account about our first time having sex until now.
Was this a consensual and/or wanted experience for you? For your partner? It was consensual and we both wanted it very badly.
Do you regret this hookup? If so, why? I do not regret this at all. Having sex with Ellie was a life-changing experience, and as strange as it may sound, fucking her ultimately led me to the woman I am now engaged to marry, but that’s another story.
What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about this hookup was how instrumental it was in blowing away any negative relationships I had formed between sex and my failed marriage and reigniting my passion and sexuality. It relieved tons of stress and gave me something to be very excited about.
The worst thing about this hookup is that we lived so far away at the time. We couldn’t hook up nearly as often as we would have liked because of it.
This was definitely a pivotal moment in my life and my sexuality. Ellie helped me gain a great deal of confidence in myself and my sexuality. This was also a new kind of sex for me. It fell somewhere in between the sometimes awkward and purely physical one-night stands with strangers I had experienced on occasion and the the deeply emotional and vulnerable love-making of romantic sex. Ellie and I had definitely connected with each other on a fairly deep emotional level, but there was a welcome absence of romance or love. It was remarkably refreshing and felt like a natural extension of the nature of our friendship.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
You have a hookup story to share? Submit it here!
What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!