What’s your gender? Woman
How old are you? 42
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Boston, USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Librarian
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 0

He Begged Me to Peg Him (Spoiler: and I did!)

How long ago did this hookup happen? yesterday

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Play Partner

How long did you know the person before this hookup? For less than a month

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? We met on FetLife. I have been a member for about a month, I took the BDSM test and came out as a switch – equally capable of taking on a Dominant or Subversive role. He reached out to me in part because I noted pegging (giving) and he had picked pegging (receiving) as an interest/fetish. I had purchased a feeldoe knock off dildo and harness on a whim, hoping to find someone to use it with.

We chatted for a few days before deciding we wanted to meet. We met for drinks, and he was as cute, funny and charming as his online profile and conversation indicated. He’s 6′ tall with warm, brown eyes and neatly trimmed facial hair, lean with long lanky legs. We hit it off, and the next week I invited him to come over. We shared some fantasies, and the evening ended with a hot make out session on my couch. We continued to chat, and I invited him to come over to try my new toy. Before the hookup, I viewed him as a potential play partner and possibly a friend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We both have kids so logistics are a huge issue. We were in agreement we wanted to get together again. My FwB decided last night he did not want to continue our sexual relationship, and I needed to be wanted, and my new friend was there. That afternoon, I invited him to come over We decided I would sneak him in after everyone was asleep – risky, but it worked. We agreed on 10 and there was some back & forth about whether the kids were asleep and if it was safe to do so.I did a little advance planning to make sure I had what I needed (condoms, lube, baby wipes, dildo & harness) stashed away in the basement, as my kids bedrooms are close to mine, and I wasn’t comfortable having him upstairs.

We ended up having a beer and a shot, and sitting on the living room couch talking to get comfortable for almost an hour and a half; a mistake, we should have jumped right in, because it was so late. I mentioned my toy, he asked to see it and we retired to the basement rec room.

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 did some kinky stuff. I showed him my toy and it turned him on, which turned ME on. There was some kissing and cuddling. He was submissive, and waited for permission to touch me, so I had to tell him what to do; kiss me; touch me; lick me. He kept telling me I could do whatever I wanted to him. We agreed to simply use stop as a safeword. He let me take his pants down and smack his ass–I’d never spanked anyone before.

He touched my crotch and it was SOAKED. And when he touched me, it was one of the most pleasurable things I’ve ever felt, just a trail of exquisite sensation in the wake of his fingers. I told him to go down on me and he immediately complied, and it was really good, started out gentle then increasing speed and pressure… it usually takes me a long time to cum and I often can’t cum at all with a new partner till I really feel comfortable. I didn’t orgasm, but was very turned on. He made me feel safe, sexy, and desired. He was a good lover–generous, a good listener and for this scenario, obedient.

I told him if he made me cum, I’d suck his cock, play with his butt, and fuck him with my strap-on. He didn’t, but, I did it anyway. I have never been with someone who let me play with his ass, so that was a lot of fun – I like it and think everyone should, and his reactions: groaning, stuffing his boxers in his mouth, leaking cum, writhing… were an incredible turn on.

I did ultimately pull out the toy, and he enjoyed me using it on him, but wasn’t able to cum, either. He used poppers before I penetrated him, which was another new experience for me. I didn’t really know what it was and had to go look it up online after he left. I didn’t try it.

Even with the harness, the dildo didn’t stay in very well. I was very concerned about hurting him and thankful he spoke up about how he was feeling.

He wanted to be spanked, and I’ve never hit anyone, and complied. The more I did it, the more we both liked it. More feedback could have been provided. It made me want to get spanked, myself; never have been.Most of the conversation was of the “How does that feel? Tell me what you need. Are you ok/Is this ok?”

It ended with it being 2:15 in the morning and him feeling a little sore/uncomfortable. I curled up behind him and held him for a little bit — walked him out and he gave me a hug and a kiss goodbye.

We discussed testing/disease and sexual history briefly beforehand. We didn’t use a barrier for oral, and skipped a condom for the silicone dildo because it was new – I sterilized it ahead of time. He took precautions (diet and cleansing) to make sure he was clean beforehand. We didn’t have PiV sex or anal sex (him on me) so we need the condoms.

First times are always a little nerve-racking. All in all, this was a very good experience.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

Did your partner have an orgasm? No

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? He texted to let me know he got home safely (left t 2:30 in the morning, and it was a school night!). I texted him first this morning and we’ve been talking off and on all day.

Ultimately, I felt good about it the next day. I know he wasn’t just after One Thing, we are more comfortable with each other and I feel sexy, desired, and confident.

My hopes were that I would overcome my shyness and feelings of inadequacy and be able to give him what I wanted. I also wanted to be able to cum, but feel like I will be able to get there. I expected to be able to make him cum, and was a little disappointed I was not able to.

My expectation is that we will continue to be play partners. I don’t see him as a long-term potential partner, but someone to help me over a rough patch of a couple of failed relationships. I have been a serial monogamist most of my life and casual sex/ethical non-monogamy is something I have believed in, but believed was not right for me, and I’m open to safely experimenting. I do feel like I can trust him, and he is a very non-threatening person. I’m interested in switching it up in the future and letting him spank me and make some demands.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, To feel better about myself, To feel more desirable, To feel more confident, Power / Dominance, Submission / Relinquishing power, Making new friends

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol, Poppers (Amyl Nitrate)

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? Very

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 mentioned it in passing to a male friend, and he winced, and made it clear he was not interested in any such thing.

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

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The best things about the hook up were that we clicked, he turned me on, we have some amount of chemistry, he was happy to go down on me, and we talked to each other and communicated well throughout. I really liked sucking him and playing with his ass. His reactions were my favorite part. And I liked that the end goal was not to have an orgasm, but just to play and have this experience together, so it took a lot of pressure off… that said, it would have been awesome to have an orgasm.

What was the WORST thing about this hookup? The timing/location was the worst part – dating is a challenge with kids, so we had to meet late and be really quiet. I feel like I’m a teenager again, sneaking around. It turned into a really late night.

And, I wasn’t expecting him to have drugs (poppers) and that freaked me out a little, wish we’d discussed it beforehand.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I am more capable of casual sex than I thought; I think this is the shortest amount of time I have known someone before becoming intimate. My nerves turned into a hum of interest as soon as he cupped his face in my hands and kissed me, and by the time he slid a finger into my panties, any inhibitions disappeared in inverse proportion to my desire.

I don’t really think of myself as a Dom, but it was a turnon to have this big guy submit to me. (I’m 5’2, and he’s at least 6′).

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? I’m really glad I did it, and it makes me want to not just see him again, but embrace my sexuality and libido. It also makes me want to explore D/s more.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I have generally looked down on casual sex, and thought of myself as “not that type of girl…” but it felt so good, I really have no regrets. I have unnecessarily repressed myself. No more!

What do you think about the Casual Sex Project? It’s enlightening and sex-positive.

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