The Teacher

by Starr

Age: 27
Race/ethnicity: Caucasian
Location: USA
Highest education received: Some college (not currently in college)
Occupation: Customer Relations Supervisor
Religious affiliation: None
How religious are you? A little
How many hookup stories have you here posted before? 0

The Teacher

How long ago did this hookup happen? 3 years

How would you best classify this hookup? New friend-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? Jay was pretty cute, a couple inches taller than me and a gorgeous body. We met through a mutual friend, and he was actually the friend-of-the-friend. We had all hung out as a group, gone to a movie, went to a festival, went to dinner, a few times that first week that we met. I was actually originally interested in the friend, but Jay was interested in me.  After a couple of days, I figured out the the friend was not interested in me, and shifted my gaze to Jay who was pretty cute. He was sweet, handsome, a total gentleman, down-to-earth, funny. We discovered through conversation that he (a school-teacher) and me (a karate teacher) had a student in common and bonded a bit over that.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One day we were casually chatting and decided to go out to dinner, just the two of us. We had both been up-front about not wanting a relationship, but being open to whatever else happened. After a lovely dinner, we went back to his place and he invited me inside, which I accepted. We started out laying on the sofa to watch a movie, but with the closeness and both of us being single, we didn’t make it far into the movie before we started making out. We eventually took it to his bedroom, partially because we knew it was heading there, and partially because he was expecting his roommate to be home at any time.

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? Jay was an incredible lover. He was attentive and all about pleasing me. He ate me out for like 45 minutes and was so totally into it! He did it some more every time he wanted a break to last longer. I came twice before we even got to his dick! I felt so appreciated. He kept complimenting my body and my skills, and we had sex in just about every position we could think of. He LOVED it when I was face down with my legs together and he was on top, entering from behind! He kept saying, “You have the PERFECT little ass for this!” I felt so confident and sexy.

After it was over, he was very sweet – I started to get dressed and he said that I was welcome to take a shower if I wanted and if I wanted to stay, that was okay – I didn’t have to just take off. I did stay, and it was the best night ever. We had sex like 4 more times between falling asleep initially and getting up in the morning!

We got together for another “movie night” a couple weeks later…that time I stuck a toothbrush and extra panties in my purse! Spent the night again, it was mindblowing AGAIN, and he was so amazing; he even took me out for coffee in the morning!

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? He would not even undress without having a condom ready – definitely took no chances, even though I was on the pill and very good about never missing a dose. We were both clean as far as STIs, no history.

What were your REASONS for having this hookup? I was newly single after eight and a half years with an abusive man who almost killed me. I was healing emotionally at that point and finally feeling confident and proud of who I am, and he was an amazing gentleman through and through, a very kind soul, and we found in each other a great outlet for sexual tension in a comfortable environment.

Were alcohol or drugs involved? If so, how much? We probably had 2 glasses of wine the first night we spent together, but none the second. No drugs.

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? Not much happened between us after the hookup. I felt grateful for such a positive experience and a kind soul. Soon after, I started actually dating someone and am happily married to him now! Jay moved to another state and is teaching there I assume – we have not kept in touch. I hope that, if he hasn’t yet, Jay finds happiness like I have found, remembers me as fondly as I remember him, and realizes how truly wonderful he is.

To whom did you talk about the hookup? How did they react? I have only told two friends about Jay, and they both were very impressed by how amazing and friendly the whole situation was.

Was this a consensual and/or wanted experience for you? For your partner? It was completely consensual and wanted for both of us.

Do you regret this hookup? If so, why? I absolutely do not regret one moment of my time with Jay. We were both unattached, consenting adults looking for companionship without the pressure of a relationship, and that’s exactly what we found. We had some things in common aside from just sex, I even helped him finish a project for his class one day, and it was honestly just amazing.

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 best thing was how incredibly kind and sweet Jay was to me and how comfortable we were with each other. Because of that, it was SO much fun and such fond memories. There really wasn’t a worst thing – nothing negative comes to mind. It has definitely solidified my belief that for myself, I need to have an emotional connection to some level with a person before I can be sexual with them. It lacked the emptiness that I’m sure it otherwise would have for me. It has also helped my confidence level, of course, being so praised for our compatibility in bed.

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

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

What did you think about this story? Tell us in the comments!

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