Nothing Like The First Time



What’s your gender? Woman
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Burbank, CA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 1

Nothing Like The First Time

How long ago did this hookup happen? 6 months

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

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than a month

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? D was tall and confident. He was very handsome in a quirky way and had a killer physique. Especially considering his age of 44 years old. He had a shortly-trimmed beard and wavy brown/blonde/grey hair.

I’ve been married for 15 years and our sex live has fizzled out in a major way. My husband just stopped caring about it. Other than that, our marriage was fantastic. We enjoy each other’s company to no end. But the no-sex thing was starting to have an effect on my confidence, ego, and vitality. I decided that the next time my husband went away on business I would try to have a one-night stand. My goal was to see for myself what I was actually missing. Maybe after hooking up once I would get it out of my system and be able to tackle my sexless life with less resentment.
My husband was planning a trip in a few weeks and I decided to join a swinger/hook-up site and start making preparations. I was still unsure if I would do anything but I wanted to have a profile set up and some potential suitors lined up if I decided to go through with it.
Immediately after signing up the messages started flooding in. Most of the guys were pretty icky lol. But there were a few who seemed OK. One guy’s messages started catching my attention and I even started noticing that I got a little excited when I noticed he sent a new one.
D really stood out from the others. His profile was actually funny and showed that he didn’t take the whole thing too seriously. Obviously I wasn’t looking for a boyfriend but I started to think that the more comfortable I was with the guy, the better. We talked about meeting for coffee and planned a tentative date the following week when my hubby would be away. As the day approached I was getting cold feet. I started to really have doubts about if I wanted to do this.But I gathered up my courage by telling myself that if it wasn’t enjoyable, I would know that it’s not for me and move on.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at Starbucks and D was really charming. He totally put me at ease. I actually thought that I wouldn’t go through with it but as we chatted more I started to really get excited about this kind of random guy fucking me. I thought the guys from the site would be over-the-top with the sexiness and cologne lol. Or boring/sweet guys. D was something else. He was very experienced and intelligent but also very quick-witted. He was able to make me feel like I was protected.
Still unsure what was going to happen, we walked to our cars. When we got to mine he gave me a hug and then kissed my neck so lightly. We started making out and after a bit I said “what now?”
He was smiling as he said “I really want to fuck you but I’m OK with whatever”-

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? D followed me to my apartment which was just a few minutes away. I was very nervous but excited. Was I really going to do this? I really didn’t feel any guilt at this point. I thought of it as an experiment. But there was something else that I found thrilling: the fact that I was doing something so unexpected and outside the realm of anyone I knew. I mean, this is pretty badass, right?
D and I started making out in my living room. We kissed for a pretty long time. We were touching each other up. It was quite sexy when he would squeeze my ass and grab my waist. I was getting very turned on but neither of us was in any rush. We eventually moved to the sofa and we continued making out. He would kiss my neck often and it made me moan. I was starting to realize that this was going to be really good. While we were kissing, D started rubbing my pussy through my jeans. He had a gentle touch but would also turn up the intensity.He opened my jeans and put his hand on top of my pussy and rubbed my clit. He would occasionally slip a finger in and get it wet before going back to my clit. He took his time and it was driving me crazy. I came pretty quickly but he didn’t stop. The rubbing got more intense and he started fingering me more. I had never been fingered so well. I don’t know what he did but he was rubbing the inside of my pussy very gently and I came over and over.
We both got naked and I finally got his cock in my mouth. In general, D had a very pleasant and mild fragrance on that he later told me was vanilla and tobacco. It was intoxicating and while I had his cock in my mouth I was very present and taking in every sense. He made me cum so hard with his fingers so I wanted him to see my appreciation. I swallowed his cock as much as I could. Then I spit out the precum and jerked him off before going down on it again.
He eventually pulled my head up and kissed me more. In between kisses he asks “are you ready to get fucked?”- I almost came just from hearing that.
D put on a condom and positioned me at the edge of the bed. He stood in front of me and slowly slip his cock in. It felt so wonderful. He started slowly fucking me. I came very quickly but, as I now understand where he was taking me, I continued to hold on while he turned up the heat. D is very sweet and funny but when he said things like “you like getting fucked by a stranger, don’t you?” it seemed authentic and not corny. He fucked me in that position for about 15 minutes as I had orgasms one after the other.
Another element that added to the thrill and excitement was D’s concern to make me feel sexy. He would blurt out things like ” Oh my God! You are so fucking hot!”

At one point I thought he was taking a break but he just wanted to reposition me. He turned me sideways and continued fucking me. His cock was hitting my pussy in an unusual yet highly-satisfying way. A long, low orgasm started building up but it was like none that I have ever experienced. As it came to a head I couldn’t breath and I had the most intense orgasm of my life. It reached its peak and stayed there for over a minute. It was electric!
When I settled down he turned me over once again. I thought we were going to fuck doggy style but he started fingering me again from behind. Then he began licking my asshole. It surprised me but I let him continue. It was so hot. I figured he was going to suggest fucking my ass next. And even though I didn’t want to do that with a man, I was going to let him. Sexually, I trusted him with my life. He actually did not try to fuck my ass. He pounded me doggy for a bit before taking a break.
During our break he was very tender but also funny. It was really incredible to be with someone who treated sex as something intimate AND fun.
We kissed and went down on each other some more and then we got on top of me and fucked me so well. Our faces were buried into each other’s and our hands were everywhere. I couldn’t get enough of him and we were soaking wet with sweat.
I was on my back and he was kneeling near my face. He was stroking his cock and I was licking his balls. He asked where I wanted him to cum and I said in my mouth. I don’t think I’ve seen anything as sexy as looking up at this man as he started to cum. I took most of it in my mouth and swallowed it enthusiastically.
We hang out for another hour before he left. There was nothing weird about it. And we left it that we would possibly do it again.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? My one-night stand with D was incredible. I started thinking that if he was that good, and he was the first guy I met, how much more is out there? I went on a little slut-streak and had a few more one-night stands but they were all disappointing. D was special. We were a great fit. I’m actually afraid to see him again because I don’t want my memory of our time together to get clouded.
The truth is– and I don’t expect many people to believe this– but this experienced really made my marriage stronger. Seeing how D could be so laid back about sex made me realize that it’s so not a big deal.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting

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? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I haven’t told anybody.

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? Realizing that wanting sex doesn’t make me a bad person and I’m proud of myself for trying something so crazy.

What was the WORST thing about this hookup? Going too far with the other guys.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Definitely. I think casual sex can be incredible.

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!