Never Expected It To Happen

by Emi

Gender: Female
Age: 25
Race/ethnicity: Caucasian
Current location: Ontario, Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Social Work
Relationship status: Single
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Hetero but willing to fall for whoever
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? 0

Never Expected It To Happen!

How long ago did this hookup happen? 2 months

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One-night stand –> fuck buddies?

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? I met “Dave” at my friend “Sara’s” birthday party. Sara had mentioned Dave a few times and had told me a little about him. I knew he was divorced, three kids, in his 40’s. Sara thought I would get along well with Dave, but I doubted I would fall for an older, recently divorced man/father of 3. At the party we ended up playing board games and somehow Dave and I were partners for one. Turns out we got along really well, ended up talking and laughing quite a bit throughout the evening. At the end of the evening, Dave offered to drive me home. Nothing happened this night. We ended up keeping in touch via text occassionally, sending the off message now and again, but nothing ever came of it. Dave was a really nice guy, smart, well educated guy. He was also pretty cute, tall and broad, dark hair with a bit of grey. I was surprised that I actually kind of found the grey to be pretty hot. His smile was amazing. I actually found him really sexy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Dave suggested we get together for coffee but I blew him off at first. Being only in my mid twenties, his life felt too different than my own life. He messaged me a few times, but I got nervous and didn’t message him back. I fantasized about being with him, but really never thought it would ever happen. I hadn’t been with many guys and I was so inexperience compared to him. I started dreaming about him quite a bit and wondering what it would like to be with an older man. After many months without talking to him, he messaged me out of the blue one day and asked if I felt like meeting up. Surprisingly, I built up some courage and said sure. I went to his house for some wine and after about an hour of chatting he leaned in and kissed me. I completely froze at first, I had never had any kind of random hook up so I was a little nervous. He asked me if it was okay if we kept going. I thought about it for a minute and at first almost stopped. I felt I shouldn’t continue, knowing it would probably lead to sex. But I really wanted to! So in that moment I just leaned in and passionately kissed him back.

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 ended up kissing on his couch for a while and then things got intense. He took off my shirt and bra and then I pulled off his. His hand went down the front of my pants and he started rubbing me. Then started fingering me. After a little bit of this I suggested we move to the bedroom and he was eager to go. We both pulled off our pants and underwear and jumped on his bed. He hovered over me, kissing my face and neck. I put my hand between his legs and felt him. He felt so big and hard, which made me a little nervous because it had been a while since I had had sex. I told him it had been a while and he went down and licked me for a while. I was definitely getting into it and getting very wet. He clearly had a lot of experience because he was so good! I had never had oral like that before. After probably 10 minutes if oral I came, which was very fast for me. I was so into it I pulled him back into me and thrust myself up toward him. Before he went in he grabbed a condom from his bedside table and put it on first. Thwn he slowly moved into me. It took a bit of time because I was so tight. He asked a few times if I was okay. I kept saying yes, but to just go slow. He was respectful and took his time. It actually was painful at first, but he moved slow, and soon he was all the way in. We moved together in that position for a few minutes and then flipped over. I was on top for at least 30 minutes, humping him and moving with him. I would lean over and kiss him as his hands moved up and down my waist and my boobs. We then flipped back over and he started humping me in missionary. He started moaning and moving faster and faster until he came. It was actually really good. I bled a little bit after. Even though I was a little sore, it was great.

Did you have an orgasm? Did your partner(s)? Yes – we both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condom. No discussion of STI history, which maybe should have happened.

What were your REASONS for having this hookup? Not sure – it had been a long time since I had had sex. I had dreamed about having sex with him and wanted to try it. I felt very inexperienced and was ready for some good sex.

Were alcohol or drugs involved? If so, how much? Small amount of alcohol

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We lay together for a little while and talked a bit. He kissed me a little bit more. Eventually I got up and left, because I had to work in the morning. I wrestled with it a bit afterwards since it was my first hook up, but I felt okay with it. We continue to hook up for sex. I don’t have any expectations that we would ever be together, but I enjoy having sex with him. We have turned into friends and seem to get along well, but nothing more than friends (with benefits).

To whom did you talk about the hookup? How did they react? Told my best friend. She asked me if we were safe and if he treated me well. She was a little worried at first, because it was so out of characters for me. But when she realized we were safe and that I, too, really enjoyed it, she was very supportive.

Was this a consensual and/or wanted experience for you? For your partner? Yes.

Do you regret this hookup? If so, why? No.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The sex was good and I have been able to learn more about myself sexually. Nothing really has been the “worst” maybe that I wish I was actually dating someone and having this sex experience with someone I actually love and care about? But otherwise, I’m happy it happened. I have learned that you CAN be a woman and have casual sexual experiences when your motives are right and the expectations are clear. Doesn’t make me a bad person. Just a life experience I am choosing to have and enjoy while I can.

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

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

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