10 Years In The Making…

by A Different Breed

What’s your gender? Man
How old are you? 34
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Seattle
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Sales
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Unique
How many sexual partners have you had in your life (including oral sex)? Over 20
How many hookup stories have you here posted before? None

10 Years In The Making…

How long ago did this hookup happen? 2 weeks ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Sex with an ex

How long did you know the person before this hookup? For more than 3 years

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? J and I have known each other since high school. She was the best friend of my then-girlfriend and we had always had an attraction to each other. She is in the petite side, but with curves in all the right places. Beautiful perky tits and a nice round ass that looks better every time I see it. We have remained close over the years, her confiding in me and vice-versa. We are always there for each other, helping each other through some difficult times, and going out to dinner on occasion. One such occasion, there were definitely sparks flying. To the point that there were some passionate kisses exchanged.
She’s been married for over 5 years but has recently been going through some issues in terms of not getting the attention that she desires. I have been in the same situation for a while, so that set the stage for meeting up at a friend’s house, instead of a restaurant this time, who was kind enough to let us use her house for the evening.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was actually my suggestion to meet up where we did, her first inclination was to have dinner again as usual. We actually found a night where our schedules lined up and we had several hours available to us. We arrived together and made proceeded to make ourselves comfortable on the couch. For her, that meant getting out the bottle of wine she brought with her. For me, it meant setting up the Bluetooth speaker with some of our favorite hits (music has always been very important to us. Several songs have special meaning for her and me). She showed up wearing all-black, right down to the thigh-high stockings and I asked her where the funeral was. We both got a few laughs out of that one.

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? It started with us listening to music on the couch, talking about various aspects of our lives. A lot of inside jokes were shared, a staple for us, and a lot of intense looks were exchanged during that time. We were sitting on opposite ends of the couch, our legs kind of pointed at each other, a fact that I joked with her about. We had joked before the meetup about how I wasn’t going to make any sort of the first move and how she just considered these two good friends “hanging out.” Despite this, I took the opportunity to start rubbing her feet through her thigh-high stockings. This evolved in to rubbing her calves and eventually her thighs, as I got off the couch and onto the floor next to her.

Many of our favorite songs were playing in the background, as we took turns playing songs from each of our phones. I was taking my time, so as to not scare her off or make her uncomfortable, always an important factor with her in these moments. It was at that moment that I made my boldest move yet, lifting her dress up to the point where I started kissing her thighs. I remember her murmuring, “you are really tempting me right now,” which was exactly what I was going for because she knows how much I delight in getting her into those moments. Things really started escalating quickly after that.

She re-positioned herself to face me, but not before changing the song to “Undone” by Duran Duran, one of our all-time favorites. We started kissing passionately, my hands running all over her body as we did. After a while, she got me to sit down on the couch as she straddled me and I started to lift up her dress to get to those beautiful tits that I used to suck on, all those years ago. I wasn’t disappointed. She undid her bra and I got to work, greedily sucking and squeezing them all over. At one point, i whispered to her, “welcome back”, referring to the insatiable alter-ego of her’s that I’m always trying to reach. She then asked, “don’t you want to taste me?”, to which I replied, “I thought you’d never ask…” I helped her out of her sexy lacy underwear and wasted no time getting my face between her legs. Teasing her at first by kissing and nibbling around her inner thighs, then eventually sucking and licking her clit like there was no tomorrow. She was moaning in absolute pleasure under my expert ministrations and this went on for a while. Then, she surprised me by turning upside-down on the couch and gave me an expert blowjob.

We then separated for a moment in order to catch our collective breaths and I proceeded to get undressed. It was at this point that I could tell she was starting to think about everything that was going on, to the point of saying she wasn’t sure she was to go any further. She asked if I would just be satisfied with just playing with my cock as I watched her play with her pussy, as she hadn’t cum yet. The proverbial fork in the road. This is where my previous experiences with her worked to my advantage, because we each know how the other thinks. I decided that this situation doesn’t come around very often and took the initiative. Without saying a word, I crawled over to her and started to rub the head of my cock up and down her pussy. She was surprised, but also drenched and we both knew that her body was starting to betray her.

We had talked ahead of time about using protection but that all went out the window as I pressed my rock-hard cock deep inside her pussy. We were both in heaven at that point as I had her legs over my shoulders and started to pound her deep. I loved watching those perfect tits of hers bounce up and down and they were really starting to have an effect on me. I had to stop for a moment because I didn’t want to cum too fast, which is surprising for me, considering I’m usually very good with holding my wad (she truly is my kryptonite in that regard). I then sat back on the other end of the couch and saw that look of concern again, which didn’t bother me. I knew what she wanted because the entire time, she was staring at my cock. Then, it was her turn to play the aggressor.

She pushed me back and proceeded to straddle me and guide my cock into her pussy. I could hear her saying “just for a second” under her breath. The moment I was inside her, she let out a very long and loud moan and I knew any other reservations she had were instantly gone. She really started grinding on me and doing that thing that she knows I love when she bounces just her ass up and down on my dick. I had to tell her to stop for a moment because I was ready to unload deep inside her pussy if she didn’t. She kept telling me, “don’t cum yet, please don’t cum yet.” She was so close. I took a moment to compose myself, to the point of even closing my eyes as she rode me, strange as it sounds. It was one of the hardest things I’ve ever had to do sexually, because her pussy felt so good and every fiber of my being was telling me to blast the back of her pussy with my cum. Nevertheless, I eventually won the battle and was rewarded with a rather loud and violent orgasm from her. I was truly in heaven, as the sound of her cumming is absolutely intoxicating to me.

Afterward, she unmounted me and laid down on the other end of the couch, telling me I could cum anywhere I wanted except inside her. I didn’t hesitate for a second. I got right on top of her, legs over my shoulders and proceeded to pound her pussy again as before. I was beyond waiting for it any longer and watching those beautiful tits bounce all over the place was too much. I started to feel that familiar feeling in my balls and pulled out at the last moment and blew my load all over her belly, which she always loves seeing.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We both felt very good afterwards. Seeing her walk around in nothing but thigh-high stockings was one of the sexiest sights I’ve ever seen in my life. I told her to come over to me so that I could kiss and rub her body all over as I sat down. She’s never been one to shy away from extra attention like that and happily agreed. My cock was still drenched in her juices as I spun her around and thanked her for the opportunity, all the while kissing her sexy ass body all over. I also loved knowing that my cock was one of the few that she’s ever been with that could make her cum like that, unassisted.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Somewhat

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Getting to experience sex again with someone from my past who I have great chemistry with and is hot as hell

What was the WORST thing about this hookup? That I can’t have it all the time

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It shows me how great chemistry with your partner can take sex to the next level.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? Hope to do it again in the near future

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Speaking for myself, sex is at the core of who I am. I’ve always believed in quality over quantity, however, so I don’t hook up with just anyone. Intelligence and sense of humor are often overlooked, even in casual sex partners.

What do you think about the Casual Sex Project? It’s a great site. I’ve always been a fan of erotic fiction, but reading actual stories about hookups like this is also enjoyable.

You have a hookup story to share? Submit it here!