All Weekend Long

by Jay

What’s your gender? Man
How old are you? 59
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? New Orleans Area, USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Public Service
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? Too many to count
How many hookup stories have you here posted before? 0

All Weekend Long

How long ago did this hookup happen? 20 years

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

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? Angela was 16, with blonde hair and blue eyes. She was 5’5″, a little chubby but very sensuously curved, and had a very cute face. I met her on an IRC chat channel and we talked for about 2 weeks. We learned a lot about each other, and a friendship developed. I learned she was in my metro area, and in fact lived less than about 2 miles from my house, though at the moment she was staying with an aunt who was close in age and about 45 minutes outside of the city while her parents were out of town.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I got off work for the weekend on Friday morning. I had been chatting with Angela, who said her parents were coming home Sunday evening, and she wanted to come on home but didn’t have a ride. Her aunt was working and couldn’t bring her. I told her I would pick her up and bring her if it was okay with her aunt, which it was. I went to her aunt’s house to pick her up. She was dressed in a pair of cut off shorts and a white top with spaghetti straps. It was obvious she wasn’t wearing a bra. Angela didn’t have a cell phone, and there was no phone at her house. We stopped at the convenience store where her aunt worked and I gave her my cell number. This way she could get in touch with Angela, and if she wasn’t with me, I would go to her apartment and get a message to her. I also assured her that I would see to it that she ate and that she got home.

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 headed back into town. We talked about it heading up. I gave her options. Since I had worked all night, and she had been up all night talking to me, we were both going to have to get some sleep before we went out to dinner. I could take her to her apartment and come get her when I got up, or she could come crash at my house and we could get up and go eat, and I could take her home as needed to get stuff or change clothes. Angela said she really didn’t want to go to the apartment as she would be there by herself. Instead, she said she would rather come crash at my house.

We got back to my place, and we kicked back and chilled. I had some coolers in the fridge, and we both drank one as we sat on the sofa and chatted. We were both getting tired. Angela jumped in the shower and I took the clothes she had with her and threw them in the washer. I gave her an oversized t-shirt that I had, and a pair of my boxers to sleep in. She got out of the shower and I jumped in. I normally sleep nude, but with her there, I couldn’t, so I wore a pair of boxers. I told her she could sleep in my bed, and I would crash on the sofa. My bed was a California King water bed, and she said that it was plenty big for both of us. I got on one side, leaving plenty of room for her to get on the other side and not have to be near me. She crawled in and slid right up next to me, saying that she normally cuddles a teddy bear at home, and since she didn’t have her teddy, she would cuddle me if it was okay. I couldn’t tell her no and I also didn’t want to.

She lay with her head on my shoulder, and her arm and leg thrown casually over me. We were on our sides, facing each other, and talking. It became apparent she was not wearing the boxers I had left her, and the arousal on me was becoming obvious. She pushed herself closer against me, with my erection against her belly, and I felt the warm, soft, fuzz of her pubic hair against my leg. Of course, the talk got risque and she reached inside my shorts and began feeling and stroking my hard cock. We talked about what it would be like the first time. She told me that she had only been with two other guys, one, 14, who came in her hand before they could ever do anything, and one, 16, but she wouldn’t let him put it in her because they didn’t have any condoms. She asked me if I did, and I told her no, but that I had a vasectomy and couldn’t get her pregnant. She seemed very nervous, but her eyes lit up to that. She grabbed my hand and slid it up under her shirt. I rubbed and squeezed her breasts, which were quite firm. While I was playing with her nipples, she reached up, and pulled my hand down between her legs and began rubbing it on her pussy, pressing my fingers into her. I could feel she was very hot and quite wet. She kissed me and I worked my fingers into her. As she worked her hips against my fingers, she worked my boxers off. I pulled the shirt up and over her head. Her nipples were erect, with areolas about the size of silver dollars and the prettiest shade of pink. I rolled her over onto her back and put my face between her thighs. I proceeded to lick her slowly, sliding my tongue over her clit. With each stroke over it, her hips rose, and she let out a little gasp. I licked her, working my tongue into her, for a good twenty minutes, feeling her cum under my mouth numerous times. Finally, I slid up above her and began rubbing my cock up and down her slit, slowly pushing my head into her a little at a time. She tensed up with a little pain but continued to pull me into her. I moved slowly and gently, and within a short time, I was buried completely into her. I began to slide in and out of her. She began to move with me, and I could feel her anxiety rising as she began to buck faster. I matched her pace, pumping in and out of her. When I felt her start contracting on me, and her body quivering, I released and squirted my thick hot cum into her. We collapsed next to each other and fell asleep holding each other.

We woke up later, went at it several more times, then showered together, got dressed and went out to eat. She stayed with me that night, all day Saturday, and Saturday night. We stayed in bed, except for the times we went out to eat, then came back to the house and fucked more. Then I took her home.

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? I took her back home when she had to be there. We continued to talk and we saw each other several times over the next year. We drifted apart when she got a boyfriend. After that, we didn’t have another sexual encounter for nearly 3 years. We are friends to this day. She is married now, but we still occasionally hook up when we have the chance.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Didn’t want to disappoint my partner, Just happened, I don’t know why, just went along with it

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? 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? The sex was phenomenal and my partner was one of the best I’ve ever been with.

What was the WORST thing about this hookup? That it couldn’t continue and lead to something serious long term.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It increased the positivity I feel toward casual sex.

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? Nothing

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? Sex has always been important in my life. I believe that love and sex are distinct and separate and you don’t have to have both, you can have one or the other. I think that too many people have hang-ups when it comes to sex.

What do you think about the Casual Sex Project? I think it is great. It is a place where people can share their stories and experiences.

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