Location: Pacific Northwest
Highest education received: College degree (eg., BA, BS)
Relationship status: Single
Religious affiliation: Christian
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? Two
How long ago did this hookup happen? August 2013
How would you best classify this hookup? Booty Call/Friends With Benefits
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? “Heidi” and I had gone to High School together. Back then she had short brown hair and was a three letter athlete and a good body on her, I can remember checking her out more than once in Math Class. I had liked her in High School and she was always friendly to me but nothing had ever happened between us.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I need to set a few things up here. I went to an ultra conservative Christian High School that foolishly taught abstinence over sex ed. We had the usual clicks, jocks, cheerleaders, nerds and bullies. I had friends, would have described myself as a nerd, and was a bit of a loner by choice, however I was never bullied due to the fact I had helped the jocks prank a rival school more than a few times so I was always on good terms with them. Now it was the same as every other high school with drugs and alcohol and sex, just all behind closed doors. I knew of a few students sleeping together, cheerleaders with reputations as sluts, etc. For example the first girl I ever had sex with was Susan, Heidi’s best friend and President of the Abstinence club. In High School girls had always made me very nervous.
Fast forward ten years. I am still a nerd but been financially very successful and been intimate with a few women and had two very serious relationships. A few months before I had gotten an email from another girl I had gone to school with about my 10 year reunion. I debated going, honestly High School was something I have really worked to leave behind and I did meet a few people that had clearly never left. However there were a few people I wanted to see so I decided to go.
It was a weekend-long event, Friday night was a dinner and a meet and greet. I had checked in and caught up with a few friends and that was when I saw Heidi and she looked incredible. She still had the body of an athlete, but had grown her hair out and had a tribal tattoo on her shoulder. I hadn’t seen her since the end of our senior trip a week after graduation. We spoke briefly at first but ended up seated next to each other at the same table for dinner and talked for a long time and even flirted a bit.
I had thought about Heidi over the years, maybe as the one who had gotten away. The second day was a family friendly day with activities for kids, I had brought my daughter for two reasons. First I don’t get to spend as much time with her as I would like and the second was pretty shameless was that my daughter had worked for me to pick up women in the past. There were a few inappropriate questions about where her Mom was (See Why I Don’t Date Coworkers), this was a conservative group but there were a lot of single parents and divorces, but my daughter was a hit with a number of the women there including Heidi. All Heidi asked me was whether me and her Mom were still together and I said no.
There was a break for a few hours in the afternoon and I took my daughter back to her Mom and went to my hotel. I was between apartments at the time and living on the road anyway so I had booked a room for the weekend. I saw Heidi swimming in the pool in a bikini and thought I was back in high school from the staring I was doing. Her body was very toned.
I went to the dinner that night for my reunion, dancing was strictly frowned upon at the high school so for the reunion it was the same. Heidi sat with me again, this time in a tighter and a bit more revealing dress. We talked for a bit and then went out into the hall for privacy and I pulled her into a kiss. I told her I had been wanting to do that since High School and Heidi smiled a bit and kissed me back. She told me I had had a shot with her in High School but never taken it and she had also known full well I had nailed her best friend early in our senior year but she said Susan was not here. She then asked me back to her hotel room.
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? Heidi unbuttoned my shirt and then asked me to help her out of her dress. I like undressing women so I unzipped her dress and kissed the back of her neck and did it slowly. She was standing there in her bra and panties and I noticed a number of scars on her right arm and side and asked about them. This upset her a bit, I had forgotten she had been in a car wreck that had killed her grandmother junior year. Still it didn’t completely kill the mood.
We started making out and I worked her back to the bed. Her bra did not stay on long and I pulled her panties off shortly after and finished undressing myself. I licked and sucked her breasts, I like boobs and will not apologize for it, and Heidi liked it. Heidi then said she wanted me inside her.
I put a condom on at this point and penetrated her. We were in missionary which is difficult for me due to a back injury I suffered a few years back. Heidi could tell I was struggling and asked if we switched positions would that help. We switched to girl on top which is my favorite and Heidi brought my hands to her hips and then rode me. Heidi was eager, enthusiastic, and a bit more experienced than I thought she would be.
I orgasmed a few minutes later and ejaculated and Heidi rode me another two minutes or so before stopping. She then leaned forward and kissed me, climbed off me and we settled in to cuddle for a while. Heidi told me it was very difficult for her to orgasm.
About an hour later she gave me oral and I came again but we fell asleep soon after. The next morning we awoke early and I was determined to give Heidi an orgasm. She said she was not fond of receiving oral so I fingered her a bit and then mounted her and ignored my back but Heidi did orgasm this time. She is truly a great lover.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I used condoms to be safe, even though Heidi said she was on the pill. After knocking up a woman who was on the pill I know that doesn’t work all the time.
What were your REASONS for having this hookup? Heidi was someone I had wanted to be with since I was 15.
Were alcohol or drugs involved? If so, how much? Not at all. Since my High School was so conservative we were both completely sober.
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? Heidi and I hooked up the next night too and have a bunch of times since. She lives on the coast eight hours from me but her Mom is not in good health so I do see her when she is in town. I also work all over the Western States and try and see her when I am in her town or within a few hours. I worked in her town recently and stayed at her place the entire time and my daughter and I spent spring break at her house this year.
These past ten months have been different for me. I have only slept with my daughter’s Mom three times, someone I have not been able to keep my hands off of for years, and had one brief morning with another woman. I find myself thinking about Heidi a lot. She is good with my daughter and I think she would like a relationship with me. A few problems though, first is the distance and second is how much I travel for work can be prohibitive to a relationship and it did so in a serious long term relationship I had. Still I have slipped and called Heidi my girlfriend a few times and she did pose as my girlfriend at a recent family dinner. I really care about her and should my work circumstances change I would like to pursue a relationship with her.
To whom did you talk about the hookup? How did they react? No one knows, Heidi has asked that unless we are actually dating not to share the details of our relationship. Still it is not something I am ashamed of so I decided to share it here.
Was this a consensual and/or wanted experience for you? For your partner? For both of us very much.
Do you regret this hookup? If so, why? Not at all
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? Great sex with someone I had fantasized about and wanted to be with since I was fifteen and it was almost everything I dreamed about. Worst part are the difficulties of perusing any sort of relationship with Heidi. This has changed my behavior a bit, I am hardly even looking at other women at this point.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? A little negative
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