Hooking Up With An Older Guy

by RedheadedCagirl

What’s your gender? Woman
How old are you? 22
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 (currently in college)
What’s your occupation? Student
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)? 3
How many hookup stories have you here posted before? First one

Hooking Up With An Older Guy

How long ago did this hookup happen? A few weeks ago

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

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 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? To start, I’m a fourth year university student. For last 2 years I’ve been renting a room with a divorced single mom. There’s a divorced dad who lives a couple floors above us. He has split custody of his two kids. A few times I’ve watched the kids for him while he has gone to work and such. I make a little bit of extra cash for school, plus it gives me a quiet place to study. So I’ve had the chance to get to know him a little over the last year. He’s tall, like 6’5″, 36 years old, and has been divorced for 4 to 5 years. He’s of average build, with brown hair and blue eyes. He’s a real decent guy, and is friendly and outgoing, and helps others in the building. He’s very popular with some of the women in the building, although it seems like no one has ever dated or slept with him. I’ve always found him really attractive, but I figured it was just what they call puppy love. I’ve always been shy, never daring enough to try anything. I’ve only ever had 2 boyfriends/sexual relationships at this point. I’m short, 5’0″ maybe 5’1″, about 135 lbs…so not skinny but not fat either. I have reddish hair, am a bit of a geek and tomboy at times. Besides, I’m only 22 and he’s 36.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A couple of weeks ago, it was a Saturday afternoon he calls my place. He was in a jam; work had called and there was an emergency, and he was wondering if there was any chance I could watch the kids for a little bit. I was studying for midterms and had no plans, so I agreed. A few hours go by, I get the kids to bed and get the chance to study in a quiet environment. Around 10 pm he comes back home, thanks me etc… He goes into the kitchen and comes out with a beer for each of us. I really don’t drink, but took it anyways. So he started talking about all the problems at work and how stressful it was, and he was happy to have it over with. So I said I knew the feeling, stress from midterms. He then tells me not to let stress take over or I’ll get old fast. Take some time to have fun. So I said you also. He then said he plans to, he’s going to have a hot shower, have another beer and watch the sport scores. I said, hey that sounds like a plan. So he laughs and says if I wanted to join him in the shower and watch tv after that’s fine with him. I laughed and said I was talking about watching sports scores and another beer. He replied with a laugh, “I don’t think you want to join me in the shower.” When I asked why not, he said because I don’t think you want an old guy like me trying to fuck you. We both laughed. I was sure I was blushing at this point. So he says, he’ll be a few minutes. I quickly grabbed 2 beers, put them in his bedroom. There’s a bathroom off his bedroom. He had the door slightly closed, I could see him taking his shirt off. I had my hair tied back. I started to take it down as I walked into the bathroom and closed the door behind me. He turns and sees me, saying I was hoping you weren’t going to be shy on me. I asked what do you mean. I was hoping you would join me. I was kind of thinking to myself “holy shit, what are you doing?” But also thought he seemed to be into me joining him, so here’s my chance.

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? So he turns around and is starting the shower. I’m so excited and basically striping down as fast as I can. He turned back around and I was pulling my jeans/panties down, as he smiles and says nice…I like. He then takes his pants off, and floop, out comes one hung cock. I guess it’s true, cut guys do look more hung. He holds out his hand and I grabbed it. He leads me into the shower first, my face was towards the shower head. My hair got wet in seconds, and the water was hot. My nipples got hard fast. He stepped in behind me. I was going to turn around towards him, but he put his arms around me and started kissing my neck and his hands were rubbing my body all over. As his hands made their way down between my legs, he commented how he like that the carpet matched the drapes. Then he started fingering me. I let out a few moans before I had to turn around. I just had to kiss him. I started playing with his cock a bit. The shower was relaxing, that’s for sure. We got out and dried each other off. He wrapped a towel around himself, but I figured why bother. I sat down on his bed, and then realized the bedroom door was open. He was over there fast to close it.

He turned around and dropped the towel, his cock bounching all the way over. I grabbed a hold of it and started playing with it and giving him a bj, but that didn’t last too long. He pushed me back and grabbed my legs and went down on me. Of the two previous guys I was with, one didn’t like doing that, the other did. As I was lying there though, I never realized how good oral was until then. I was trying not to be to loud, but I was having a hard time. I had a one of the best orgasms that I didn’t have to give to myself. He stopped for a minute and took at drink. I was about to sit back up and continue giving him a bj, but he grabbed my legs and turned me over. Next thing I knew I was letting out a huge moan as he slid his dick right into me and started thrusting hard. He alternated from slow and gentle, to hard and fast. This went on for a bit. It was getting hard not to be too loud. After a bit, he turned me over onto my back. I wasn’t sure if he was done or not, but then he got on top on me in missionary and we started that way for a bit. It was more of a slow, gentle, passionate thing with lots of kissing. I was really enjoying this. Finally, he made a couple of hard thrusts and let out out a huge moan, I could feel him cumming. We kissed a few more times before he got off of me. I was thinking, should I go get dressed, but he put his arm around me and cuddled with me. First time for that. This was amazing.

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? The next morning, I got dressed early and got out of there because I didn’t want the kids to catch me there. He took this as me being upset about what had happened. So I went down later on in the evening to talked to him. I told him that I wasn’t upset. I admitted that I had a little bit of a crush on him and was happy and excited it happened. He admitted he finds me attractive, but didn’t want to seem like he was taking advantage of me. I said I know that a relationship isn’t likely with the age difference, but I was more that interested in doing it again. I’m okay with a fwb type thing. So we’ve gotten together a few times since then.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, 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? Small amount of alcohol or drugs, not enough to feel it

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

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? My roommate kind of figured it out when I didn’t come home that evening. I said I had fallen asleep on the couch before he got home and just let me sleep, but she knew better.

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? I guess I came out of my shell a bit and was more daring than normal. Had great sex with an attractive guy.

What was the WORST thing about this hookup? Can’t think of anything.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Honestly, there’s a guy in a few of my classes I like. I’ve got a little more confidence to try something with him. lol, We’ve been talking a lot in class and online. He commented on a picture of me in a bathing suit from the summer.

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

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

What do you think about the Casual Sex Project? Cool. I love reading the stories people post. That’s why I added mine.

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