The Anti-Valentine’s Day



What’s your gender? Woman
How old are you? 37
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Lawyer
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 18
How many hookup stories have you here posted before? 0

The Anti-Valentine’s Day

How long ago did this hookup happen? Last week

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

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? I met him online. We had sexted and hooked up twice before this evening. Both in-person encounters involved little to no talking, so other than sexting and sexing, we didn’t know each other at all. Matter of fact, pretty sure he had never even taken his clothes off. He solely pleasured me both encounters. But it was unreal, truly mind-blowing stranger sex, so I was very excited to see him again.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It happened to be Valentine’s Day. But this had absolutely nothing to do with the holiday. The night before, I asked if he’d be able to come see me, and told him I wanted to see him. We spent the night sexting and I sent him some photos. He had been priming me for this evening–which I did not realize at the time–since the first meeting. I showed interest when he got a little rough with me and he liked that interest. There was definitely some power play when we got together and in our sexting, but nothing beyond some gentle requests and him twisting my nipples. So day of, we both had to work. But we were still texting throughout the day. He told me he got some surprises for the evening and I would have to send him photos of various parts of me to get a return photo of the surprise he got for that part of my body. This was a super fun game. Good foreplay can start hours before the main event. As the day progressed, I got photos of under-the-bed restraints, a double-ended slapper/feather tickler, and nipple clamps. Serious planning on his part and this was way outside of my past zone of sexual activity. I was both excited and nervous. He tells me to make sure I have ice cubes and candles ready for when he gets there. I left the door open for him and when I got out of the shower, he was in my bedroom.

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? When I walked in to my bedroom, he gently rubbed his hands from my neck down my back, to the back of my things and then up the inside of my legs, to my stomach and my breasts. So gentle. Then he pushed me down hard onto my bed, ordered me to put on a blindfold, and strapped me to the bed. I was super turned on, and was shaking by this point with the excitement. I felt so vulnerable, so exposed. But once I was restrained, he was gentle again, lightly kissing my body, caressing me. He went down on me and started finger fucking me. In this man’s hands, this particular combination will get me to orgasm in 20, maybe 30 seconds once I’m already excited. And I was so excited. He gave me a few orgasms in quick succession. But he had barely gotten started. I was very relaxed now and was starting to settle into the blindfold and restraints. My sense of touch was heightened beyond anything I had felt before. He started to play with that….the feather tickler up and down my side, and then the slapper right on a nipple. Searing pain that sent shock waves through my body. This man knew how to apply the perfect combination of sweet caresses with searing pain. (He later proudly recalled that he gave me 15 sharps smacks on my right nipple with the slapper before topping it off with 20 on my left). Then he finger fucked me more and got me to come at least 4 or 5 more times before he got out the ice cubes. Him rubbing the ice cubes on my nipples, which were still humming from the slapper, was excruciating and delicious at the same time. He gave me a bit of a break then and rubbed the ice cube up and down my legs, my sides, and my neck. I started to relax again and he gave me the rest of the ice cube to suck on. An incredibly sweet gesture at the time. He was ready to start amping me up again, but started slow and sensual. Kissing my ice-cooled skin with his warm mouth, his beard gently tickling every inch of my body. He started at my neck, went all the way down to my feet, sucking on my toes, massaging my body, back up my body… it felt like I was floating. He does this thing when he finger fucks me. I don’t even know how he does it, but he hits my g-spot just perfectly and he gets me to come multiple times within just a few minutes. So he finger fucked me to multiple more orgasms…5? 7? I don’t know, a lot. I had just enough wiggle room in the restraints to twist my body so I could almost lay on my side. He arranged my body for the best strike and gave me a downpour of hard spanks and slaps interspersed with gentle rubbing on my ass. I was in ecstasy. Every sting felt better than the last and every gentle caress was just a tease. My entire body was pulsing with raw sex and pain and lust. Seriously indescribable. He helped bring me back down to earth by turning me back over onto my back, and gently rubbing my clit. Just slow, gentle rubbing. Once I started coming back, he took the restraints off, gave me some water, and slid his fingers back up inside my pussy. I fucked his hand for a while and had a seriously powerful squirting orgasm. I was still craving his touch and settling back into the real world outside of the cuffs and blindfold. For the first time, he took off his clothes when I begged him to fuck me, and he did, and it was great. First with him standing at the edge of my bed with me on my back and legs in the air, then I think a quick missionary, and then he asked me to go down on him. Yay! Finally! I did, and he kept both hands on the side of my face/back of my head to make sure I went deep enough for him. That feeling of his hands on my face with his cock way down my throat was incredible. He was strong and confident, but not forceful. It was tender and sensual, not what I usually think of when taking a cock down my throat, honestly. Then I got back on top of him and rode him until he came. All in all, he came once and I say I came upwards of 30 times. I lose track with him…. There was one orgasm near the end that just kept going and going…..not like waves, like one thrumming vibration radiating through my body for what felt like hours, but he said lasted about 2 minutes. I cleaned us up a bit. Then we laid on the bed and talked about what we liked and how the experience was. He left shortly thereafter and I had the best night’s sleep of my life. So awesome!

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? I basked in the glow….Felt absolutely awesome about it the next day. Super excited that I was learning about some play that I had never tried but totally enjoyed. I honestly couldn’t stop reliving the night all the next day and probably the day after too. It was some seriously earth-shattering sex. It’s only a week later now and our dynamic has already changed a bit. We’re playing with more power exchange, it makes things that much more exciting. The sexual chemistry is off the charts and we are having a lot of fun.

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

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Submission / Relinquishing power

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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 haven’t told anyone.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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 experimentation. Sensory play, bondage, submission. This is all totally new to me. And I am discovering it fits me really well. The best part is just knowing all these ways that my body and mind work. This guy really gets the mental aspect of sex….how to draw out the tension, how to tease, how to elicit desire, how to bring me up and then back down. That is seriously fucking sexy.

What was the WORST thing about this hookup? There was no worst thing….maybe that it didn’t happen sooner?

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This encounter helped me explore my sexuality and discover some new things that are super erotic for me.

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

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

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