Seducing a Long-Term Friend to Be a Friend-With-Benefits



What’s your gender? Man
How old are you? 45
What’s your race/ethnicity? Southeast Asian
What continent do you live on? North America
What country and/or city do you live in? A large metropolitan city
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Finance
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 14
How many hookup stories have you here posted before? 0

Seducing a long term friend to be a friend with benefits

How long ago did this hookup happen? 4 months ago, this past summer

What was your relationship status at the time? Single

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

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? Meredith and I have known each other for ten years as friends. She is eight years younger than me. She is a nice person with a good job and has her life together, except where it comes to dating and relationships, she hasn’t been doing too well. We definitely get along and see things the same way. While we went out to do things together, we never dated, because she was just not my “type”. She didn’t look bad. In fact, she can be rather attractive. She is 5’8″, big boned, athletic and on the heavier side, while I prefer women that are more petite or slimmer. In fact, I think her heavier build is not appealing to most men, and that has not helped her self-confidence.

Over the years, I’ve seen her go through a couple of relationships that never worked out. The most recent one ended pretty badly. They were about to get married, and then her fiancé turned out to be very abusive. I heard about the break-up a few weeks after it ended. She started running again (she’s a very good marathon runner) and decided to attempt a triathlon to give her life some new focus. Since I bought a new bicycle, we started cycling together to help her train.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On the day of the triathlon, I helped her out by driving her bicycle to the event and taking care of her personal belongings. I waited for her at the finish line, because I knew competitors appreciate this kind of support.

When she came though the finish line, she was ecstatic and overjoyed that she was able to complete the race. We hugged. Feeling her sweaty body through her tight one piece swimsuit was arousing. Looking at her after such an intense athletic event made me think that her body was more athletic than I had appreciated.

She was exhausted and wanted me to drive her home so she could shower and rest.

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? When we got back to her place, she was still on an emotional high from the event. We sat on her living room sofa while she excitedly told me every detail that happened during her race. Our bodies were facing each other as we were talking. She was still wearing her swimsuit which left little of her body to the imagination. Her body looked sexier than I had ever recalled, maybe because of the training or maybe because this was the first time I saw her with so little covering her up.

She was leaning back against the side of the sofa. One leg rested on the sofa bent at the knee, and the other leg stretched out across the floor. With her legs spread out like that, I had full and direct view of her crotch. It excited me to imagine what was behind that crotch panel of her swimsuit. I felt an irresistible urge to eat the pussy between those long legs of hers! As she kept talking, I saw her long flowing dark hair and natural face, She became very fuckable in my eyes. I leaned in and kissed her. She stopped talking and looked at me in surprise. I reached in and kissed her again. We started kissing more passionately. I took off her swimsuit and my clothes as well. She pulled back and said she’s sweaty and should take a shower first. I told her that the smell and taste of her sweat really turns me on. She was hesitant, but also eager and excited. She let me go down on her crotch and I started licking her. She tasted salty and there was a sexy smell. I licked her pussy, thrusting my tongue in and out as far as I could. She was moaning. Her taste became less salty as juices starting flowing out of her. By now, my cock was very hard and I wanted to have sex with her. I got up and as we looked into each other’s eyes, I held my penis and stroked the tip around and around the entrance of her vagina, then pushed it in a little and pulled it out, doing this a few times. I was wondering about condoms, and I didn’t know what she was thinking. We just kept looking into each other’s eyes. Then I just pushed all the way into her and started fucking her. All the while we were fucking, I was telling her how good it feels to be having sex with her, and she was telling me how good it feels to be having sex again.

We switched positions a few times. I wanted to hold and feel her body in different ways and to push my cock into her at different angles to really feel her vagina. As I felt my orgasm coming, I screamed that I’m coming. It all felt so good that I didn’t pull out. We looked into each other’s eyes, but Meredith didn’t look upset. In fact, she was all smiles and said I felt SOOO GOOD.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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 cuddled and talked about what just happened. The relationship question came up. She said she was still getting over the last relationship to start something. I wasn’t sure if this was true or whether she just said this to avoid a relationship with me without jeopardizing our friendship, or maybe she just didn’t know. I was also not sure about a relationship with her and did not want to jeopardize our friendship. I said I understood her feelings about her last relationship. I said the sex was heat of the moment. I really wanted it because I found her sexy and I am comfortable with her. She liked that answer. We both agreed that we can continue to be friends and see whether a relationship can happen in time. That conclusion seemed to be a relief for both of us, but it also seemed to delay something we need to address sooner or later.

With that out of the way, she went to take a shower. We were still touching each other quite a bit and maybe it was the afterglow from the sex and her high from the triathlon: we ended up taking a shower together. Then we went to her bedroom to have sex again. Again, it was unprotected sex. We certainly were not worried about diseases as we knew enough of each other’s relationship history, or lack thereof! As for risk of pregnancy, I already came inside of her the first time, so we said what the heck, since it felt so good to be intimate like that and to feel the wetness and the tightness and the feeling of me cumming inside of her. But we never talked about what if she did get pregnant. I wondered if deep down, she was hoping this will happen. As for myself, it feels like, if it happens, maybe this will be the event that drives me into something long term. She certainly doesn’t have any bad points except that she was not originally my body type. For that moment, we just spent the rest of the afternoon in lust in her bed having sex. I took her out for dinner, and then as I was about to drop her off for the night, she said it’s hard to say good night after such a satisfying day like that. So I slept over at her place and we had sex a third time.

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, Attraction to partner(s), Seeing her in that tight competitoin style swimsuit with her thigh gap and crotch pointed at my face really turned me on and just brought me over the edge of desire.

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? I don’t know / I’m not sure

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… yet, because there will be some explaining to do, as I will describe below.

How would you best summarize people’s reactions about this hookup? Other

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It was the first time I had unprotected sex. I’ve had my fair share of partners, but I always used condoms. With Meredith at that moment, I was just so in lust that I went for it.

What was the WORST thing about this hookup? Fucking my good friend after she was on a rebound, and not even knowing at that moment if I wanted anything long term with her, but maybe that didn’t turn out too bad as I will explain below.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I have always been very picky about who I wanted to date and have sex with. It is actually good to just let my sexual urges take over the doubt and go for it. Fucking someone without thinking about anything long term might just be what I need to progress with my relationship well-being and sexual well-being, as I will explain below.

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? We started to have sex with each other regularly after that hookup. In fact, we were having sex three days a week or more. Some weeks, as much as five times. We didn’t act like fuck buddies. We actually did things together like go out for dinners or go cycling or see a movie before having sex. Despite that, we never said we were dating or said we were a couple. She was leery of another failed relationship, and I was still wary of getting into something long term with her. But all that frequent sex was building an attachment between us. The other thing was that we never used protection. We both really enjoyed fucking recklessly like that. We even did it when she was on her period. Pulling out with her blood on my cock was strangely intimate. We actually enjoy period sex. But alas, that won’t be happening. We just found out last week that she is pregnant! Now we are a couple! I think deep down, I was hoping that something like this would make me make a commitment to someone long term. I’m happy for her too.

What do you think about the Casual Sex Project? I’ve been reading this for a while. Being able to write and contribute to this has helped me work out my own feelings.

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