What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Some college (not currently in college)
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 1
Switching Places In The Affair
How long ago did this hookup happen? 3 years
What was your relationship status at the time? In a relationship (monogamous)
How would you best classify this hookup? Affair/Fuck-Buddies
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 was 24 years old with brunette hair and blue eyes. She’s 5’1″, average weight, 32F breasts, and a nice bum. She was recently divorced with 2 kids. I’d known her for roughly 10 years and for the past 2-3 years, we’d been involved in an ongoing on again off again affair. She’d married at 19 because she got pregnant and her husband turned out to be an alcoholic prick.
I can’t recall how we reconnected, but we exchanged numbers and began texting frequently. Within a few months, the texts had taken on a very sexual tone and it had come out that we’d both been very attracted to each other in the past. She confessed she’d gone so long without sex she was ready to have an affair, and things progressed quickly after that. We met up one day and had a very hot make-out session that she cut short in a panic. However, within a week we’d made arrangements and had sex for the first time. The sex was explosive, the best blowjob and pussy I’d ever had, and she was glowing with pure satisfaction. Our affair carried on for several years. The sex was always amazing and we admittedly had feelings for each other, but given the affair, we couldn’t trust each other. I ended up getting a girlfriend around the time she started going through her divorce and we saw less of each other.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It all started on a Friday night, I was out for a friend’s bachelor party, jumping from bar to bar with strip clubs in between. We were hanging out at our second bar when I got a text from J, asking what I was doing. I told her I was out at a bachelor party. She asked what time I’d be back, and I told her I had no idea and asked why. She responded with “Because I’m out with the girls getting drunk and I’m already horny.” I was a little caught off guard and asked how she expected me to help with that. Her response, “Well, I was hoping you’d come put that big beautiful cock in me later tonight.” I was speechless. Me coming out to this bachelor party had resulted in a big fight with my girlfriend and on top of that, the relationship was already getting stale. I’d been the other guy countless times, but I wasn’t sure if I was ready to do the cheating. It didn’t matter though, we’d taken a limo downtown and if I were to take a taxi it would be an easy few hundred, so I told her I didn’t think I could make it. The texting continued though, and she was practically begging for it. Then she started sending pictures. I was getting hornier by the minute, but I simply couldn’t make it work that night.
Saturday rolled around and my girlfriend was still bitchy about me going out with my buddies and she wouldn’t come over. I was still pretty horny from the night before, so I started looking at the pictures J had sent and I decided to text her and ask if she still needed help with what she had asked last night. She responded by apologizing and saying she shouldn’t have done that and I’ve got a girlfriend now and so on and we left it at that. Later that night, I was still insanely horny. The slightest sexual thought was getting me hard, and I knew she wanted it, but she just needed more of a push, so I pulled my hard cock out, snapped a pic, and sent it to J. About 15 minutes went by and I was starting to think maybe she wouldn’t respond and I’d just have to rub one out, but then I got a response “Pick me up at the end of my parent’s driveway.” After the divorce, she’d gone back to her parents who had a farm out in the country. It was a quick 5-minute drive, so I rushed over and there she was waiting for me. She hopped in and immediately started kissing me as she reached into my sweatpants and started jerking my cock. She instructed me to go to a park down the road, but there was now a gate so I continued driving and looking for a spot. I was so horny I just ended up pulling over next to a field. I figured out here at this hour no one would see us.
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? We both looked at each other and said it was good enough. She went down and started giving me head. I leaned my seat back as she did her thing, and a few minutes in though it occurred to me I’d forgotten to bring condoms. When I told her, she gave me a kiss, smiled, and said “Well I’m not married anymore so we don’t need to worry about anyone finding your cum inside me.” With that said, I rushed to the passenger side of the truck and peeled off her pants and her thong. She spread her legs for me and I pulled her to the edge of the seat. We’d always used condoms and her pussy was still one of the best I’d ever had so when she grabbed my cock and lined me up we both let out moans of pure satisfaction as I pushed inside. I started fucking her as she told me how much she’d missed my cock and how good it felt. I hadn’t had sex in two days and now I was fucking her bareback. I knew I wouldn’t be able to hold out long. Luckily it wasn’t taking her long either. She started clawing at my back begging me not to stop as she wrapped her legs around my waist, then she squeezed me tight and let out a long moan as her orgasm hit. Her entire body trembled and her pussy began squeezing me as I delivered my final thrusts. My cock throbbed as it filled her.
We were both sweaty and panting. I didn’t pull out for several minutes, and then we got dressed and I drove her back to her parents. Our kiss goodnight quickly turned heavy and her hand was back on my cock. She pulled it out and told me to lean back. I did and she went to town on my cock. She was truly skilled at sucking cock, and she never complained about how long it took. Sometimes I think she enjoyed giving head more than I enjoyed receiving. She gave a lot because her husband hated blowjobs. Despite having already cum that night, it only took about ten minutes before I was shooting another load in her mouth. We kissed again and called it a night.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, more than one
Did your partner have an orgasm? Yes, multiple
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? The next day I didn’t feel guilty. My morals are a little messed up anyway. I’d fucked this woman for years while she was married so I was just concerned about covering my tracks. J got wetter than any woman I’d been with, and our late night hookup was no exception, as there were obvious signs of her pussy juices dripping down the side of my passenger seat. A quick detail dealt with it though. I broke things off with my girlfriend shortly after that night as things continued to be rocky between us. I had no expectations, but J and I continued on as we always had. She started dating again all the while we continued fucking. We finally ended things for good and she got married again, we still maintain a friendship, however, given our history, we keep our distance to prevent our affair starting up again.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection
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
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? Finally fucking her bareback.
What was the WORST thing about this hookup? Still having to be cautious.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The whole affair in general has in a way changed how I look at things. We’d known each other since we were 15 or so, then we hooked up in our early/mid-20s, and after that, we literally fucked every time we were alone together regardless of relationships. The sex is explosive, however, given how we went about it, we can’t trust each other, so casual sex is as far as we take it. Even though we said enough is enough and we haven’t had sex in years we still know if we are left alone, odds are, we will fuck.
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!