Bareback Sex Within Three Hours of Just Meeting

by Dan

What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business development
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Late bloomer
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 2

Bareback sex within three hours of just meeting

How long ago did this hookup happen? around 2000

What was your relationship status at the time? Single

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

How long did you know the person before this hookup? Just met that day

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? Before online dating, there was a telephone dating service called Telepersonals. You called it up to listen to ads from people seeking relationships or casual encounters. The women’s ads seeking casual encounters were very explicit. While there were no photos, listening to the women describing in detail about what they wanted was enough to get me excited. There was one ad that was quite ordinary. It sounded authentic, with no mention of anything sexual. I figured I stood a better chance of getting a response from this ad than from any of the more explicit ones. I responded to the ad without any sexual hubris and left sincere sounding details about my background, career, and interests. That strategy worked. “Anna” got back to me. We spoke by telephone. Apparently, she seemed to like what I said about myself to be sure she wanted to move things forward with me, whatever that was. When we made plans for a dinner date the next evening she added, “don’t forget your toothbrush” just before I hung up the phone. I couldn’t believe she was already convinced that she wanted us to have sex so soon.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I picked her up at her apartment. Once I saw her, I was disappointed. She was wearing an old-fashioned winter coat and heels that looked more suited for older ladies, even though we were both 32 at the time. She was 5′ 5″ with brown shoulder length hair, about 135 pounds, and looked older than her age. She was a smoker and started smoking in the restaurant. She was good humored and friendly. But she was also checking messages from her cell phone, most likely to listen to the other responses to her Telepersonals ad. She didn’t do that it a way that was rude. It just looked like it was ADD, or maybe this was all fun and games to her. The conversation was okay over dinner. Nothing exceptional. We both humored each other, keeping things friendly and positive. It was snowing that night, so after dinner, I held on to her so she wouldn’t slip as we made it back to my car. When we got back to her apartment, she invited me up. We started having drinks, and then out of nowhere she started kissing me aggressively. Her teeth were banging into my teeth. It felt like she was an inexperienced kisser. Anyway, I just went with it. Within a few minutes, we were both stripping off our clothes.

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? While she wasn’t my type, seeing her in her black panties and matching black bra turned me on. I originally felt she could stand to lose 10 or 15 pounds, but those silky black panties showed off her legs and ass in a very sexy way. That taught me that ever since then, if a woman did not appear sexy upfront, seeing her naked could quickly change my mind. I had a full on erection by now. I took off her bra and panties and we continued making out. I was so horny I pushed the tip of my cock against her pussy, but she whispered, I’m not ready yet. We continued kissing while I fingered her pussy lips. We moved into her bedroom. She kept whispering in my ear how much she wanted me, and then she whispered “let’s make love.” By then, my senses came back. I didn’t bring a condom, as I had not expected we would be having sex. I asked her if she had a condom. She said “no, but don’t worry.” I asked what do you mean? She said she can’t get pregnant. “Why” I asked? She replied “I just can’t.” She kept kissing and fondling me and wrapped her leg around my waist. I was worried about STD’s, especially from a woman who seemed so easy, and what’s this about can’t get pregnant? Did she have Chlamydia at one point? I could smell the stench of cigarette smoke in my hair as I laid there naked, in the bed of a woman I had just met three hours earlier, interested in fucking bareback. It was all so slutty. Then I thought, but this was what I always fantasized about in all my sex-starved younger years. I want this!! I wanted to be a slut now. With that thought, I was in! I started kissing her again, I quickly got really hard again, and I penetrated her. She let out a moan of satisfaction. Her pussy felt hot and tight. I started thrusting. She lifted her legs and pulled her knees towards her, allowing me to penetrate deeper. I pushed my body forward to allow me to take longer and deeper strokes. Feeling the wetness and warmth wrapped around my cock felt so good. Her moaning encouraged me to pound harder and deeper into her. I remembered all the times I heard neighbors having sex, the woman moaning loudly, keeping me awake with jealousy, making me horny, and now here we were doing that to the neighbors around us. I loved it! At the same time, I was still worried about catching some STD, and I think that worry was what kept me from climaxing, despite the intensely pleasurable feeling in my cock. She was enjoying the prolonged sex and this was also fine by me. She finally yelped, “I’m coming.” Since she already orgasmed, and we were fucking hard for a satisfyingly long time, I was ready to climax, but I still couldn’t. So I grabbed her calves, pushed her legs above her head and pounded into her harder like a jackhammer, hoping the intensity would bring me off. Anna loved this even more. By now, she was moaning very loud. I was sure the neighbors all around the apartment could hear us. It felt great, and with that, I had an intense orgasm. It felt so good as my semen shot inside her with each ejaculating pulse.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? We laid in bed to rest for a bit. Then I started freaking out about catching some STD. At the same time, I was still enjoying the sleaziness of the moment. I was torn. I slept over. We were about to have unprotected sex again in the morning, but by then, I lost the feeling. She was upset that I would not have sex with her again. We left on good terms. She tried to call me a few times after that, left a few messages on my answering machine, but I never returned her messages. I also got tested and I was okay, thankfully. About a year later, after a rough patch at work that was resolved, I realized I should take life easier, so I called her up. She was in the process of moving back to her home town, because life was not happening with her here. That’s how we said good-bye.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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 didn’t tell anyone.

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? A little bit

Do you regret this hookup? Somewhat

Why do you regret this hookup? I was worried about STDs. Thankfully I was fine. I also regret using her for sex, even though she gave enthusiatic consent and initiated it. She was needy and wanted a relationship, and was using sex to get it. She was a good person, and I regret if I hurt her in any way.

What was the BEST thing about this hookup? Many things. Feeling slutty by fucking someone I just met three hours earlier. It wasn’t just the emotional feeling. The sensation of unprotected sex combined with the emotional feeling of being slutty was powerful. I also learned how to fuck aggressively, which served me well with later partners.

What was the WORST thing about this hookup? Possibly hurting her feelings.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It increased my sexual self confidence. I also learned that even if I was not sexually attracted to a woman on first sight, I could change my mind after seeing her naked or in her panties. I used to think sex was best with a relationship. This experience changed my outlook to feel that it is okay to have sex earlier and see where it leads.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? No.

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? I gave my comments in an earlier story.

What do you think about the Casual Sex Project? I gave my comments in an earlier story.

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