Age: 35 Now/20 Then
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Relationship status: Single
Religious affiliation: Catholic
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 22
How many hookup stories have you here posted before? A Few
How long ago did this hookup happen? Fifteen Years
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…)? Summer Fling/Short Relationship
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? Grace is the younger sister of my childhood friend Evan. We had all grown up together, our parents had been friends before we were all born. She used to follow me and Evan around as kids, and I had thought of her as a bit of a pest.
Before this I hadn’t actually seen Grace in about four years. I had gone to college early. Evan and I had stayed in touch via email, this was before Facebook and Skype.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Evan got married right out of high school. He had asked me to be a groomsman in his wedding, I said yes. He had also asked me to be backup best man a few months prior, his brother was in the Navy and there was a chance he might not be home for the wedding which ultimately proved true and I was left with Best Man duties.
The maid of honor was also in the service so Grace had offered to handle those duties until she arrived the day of the wedding. I had left for college early and hadn’t even been home the previous three summers, and had not seen Grace in years.
I was back home about two weeks, just out of a relationship (See The Professor) when I saw Grace for the first time. The wedding was at a camp and Grace and I were there all week, bumping into each other. Honestly I thought she was a little plain with curly brown hair she kept tied up in a bun and she dressed very conservatively. However we had spoken at length about the wedding and caught up and actually had stayed up the previous night talking well into the morning. We had flirted a little, nothing serious though but she did kiss me on the cheek and confessed she had had a crush on me as kids. I was twenty and Grace had turned 18 a few weeks prior.
I was considering asking her to dinner after the wedding, but I had gotten a call she wanted to see me in her room. I walked in and Grace was in the bathroom and came out wearing nothing but a black strapless bra and thong, and heels. She had become a rather curvy woman, large full breasts and hips and a great ass. She had strained her hair and put on makeup and in that moment, I really wanted Grace. The heels put her at the perfect height for kissing and I put my arms around her waist and pulled her into a kiss. I let her hair down telling her I wanted to see what that looked like. Lets just say members of a wedding party hooking up is cliché for a reason.
What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I pushed Grace back towards the bed and pinned her, and she unbuttoned my shirt. I can remember her bra popping off rather quickly and she kicked her heels off. I can remember her breasts felt great against my chest. I finished taking my clothes off and pulling her thong down and we made out naked for a long time. She sucked my nipples, first time I had ever had a woman do this and I liked it. I returned the favor and licked and sucked her breasts for a while.
We decided it was time to do the deed and I stuck my cock in her and began to fuck her. I continued to kiss her as we went. Honestly the sex part wasn’t that great, while I was not the first Grace was not very experienced. It’s something I found often happens the first time with someone that the sex is not that great. Grace actually orgasmed rather quickly and vocally, a first for her and something I am quite proud of. I couldn’t finish and Grace after relaxing for a few minutes finished me off by hand gently. She was quite good at that. We fell asleep shortly after cuddling.
We awoke our bodies intertwined, basically Grace fell asleep atop me. She smiled a bit and I rubbed her back, and she moved down and gave be a quick blowjob. After I came in her mouth she jumped out of bed and I gave her a swat on the ass and she laughed a little and said she liked that. I dressed quickly and snuck out of the room, not wanting to get caught leaving her room by anyone.
We hooked up every night until the night after the wedding. That second night was something special, Grace had gone down and hit Victoria’s Secret and bought a red lace bra and panties, and she did a little dance and strip tease for me. Sex that second night was much better, I took her in doggie style this time and we both orgasmed around the same time and I came inside her. Our other nights were good too and eventually the wedding came and we stayed one more night because it was very late.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Those first two nights Grace and I were very foolish, giving into passion and not using any protection since we had no condoms and I did finish inside her once. Grace did have a pregnancy scare about six weeks later, having missed her period but a Doctor’s visit confirmed she was not, I went with her. Grace also went on the pill after that. I use this as a bit of a cautionary tale to everyone out there about the importance of protection, a baby lasts a lifetime and an STD can kill you.
What were your REASONS for having this hookup? I was young and horny, enough said.
Were alcohol or drugs involved? If so, how much? Not by me and not by Grace as well.
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? Things between me and Grace were awkward outside of the bedroom for the rest of the wedding prep and the wedding, inside was something special. We danced together and spent the night of the wedding in my room.
Grace and I were a couple the rest of the summer. Outside the bedroom she was a lot of fun and she got me to do things I never would. A big one was we went skinny dipping in the river near her house. Inside the bedroom she was eager and willing to learn, trust me the guy after me owes me big time.
September rolled around and I had to return to college, and Grace was going to college in a town across the country, something I talked her into. We decided to make a clean break and split up. I think things could have turned serious if we weren’t leaving. I met Lindsay in the fall (See My Son’s Mom) and I didn’t hear from Grace for a while.
We have hooked up a number of more times over the years, a week she visited DC I offered her my couch and it did turn into a week in my bed. However we never were a real couple again. She friended me on Facebook a few months back, I was single at the time so I saw nothing wrong with it. From our chats I get the impression Grace was feeling me out for a relationship but I had heard she had been divorced three times and had four kids by four different men so I kept my distance. However I do look back on my time with Grace fondly, she was my first real girlfriend.
To whom did you talk about the hookup? How did they react? Evan punched me out when he found out, he was that type of guy.. He caught us making out in the parking lot and I was grabbing Grace’s ass with both hands. She did get between us or I would have hit him back at his own wedding. Evan and I actually shared a laugh about this recently when he and his wife visited me. Everyone knew about us since we were a couple for a few months, her parents didn’t care for me though since I was older.
Was this a consensual and/or wanted experience for you? For your partner? For me very much and for Grace as well, it meant time with an older college guy.
Do you regret this hookup? If so, why? Mostly not, but things between me and Evan were tense for a while. We did patch things up months later after Grace and I split.
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? Mostly the best parts between me and Grace were out of the bedroom, however that was the most open and honest I had ever been with anyone and I liked it wasn’t just about sex but I did enjoy the sex too. Worst part was getting punched by Evan, that hurt. As I said. this was my first real relationship so it opened me up to them and I learned a lot.
All things considered, how POSITIVE was this experience? Very positive
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