Late Night Anal Play

by cupcake

What’s your gender? Woman
How old are you? 19
What’s your race/ethnicity? Native American / Alaska Native
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Some college (currently in college)
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Finally starting to get comfortable sharing it with others.
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

Late Night Anal Play

How long ago did this hookup happen? 1 day ago

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 3 years

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? The guy I’ve been hooking up with for the past few months invited me over to his place. I’m on my period and we’re not to that point in our relationship where we’d feel comfortable with period sex which I’m totally fine with (I’m not sure if I’m ready to bleed all over him yet anyways). I went over expecting some cuddling, making out and giving him head (which I love doing) and I was pleasantly surprised. He’s a mixed guy (super sexy, soft skin, dreads, ugh) more than 10 years older than I am but we’re super comfortable with each other because we were good friends before we started seeing each other intimately.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We’ve been friends with benefits for a few months now and he asked me to come over after I got off of work. I went home, took a quick shower and went.

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? I laid down next to him in bed and we cuddled, talking for a while and absently watching the movie that was playing. He was already only wearing shorts and he began to take my t shirt and leggings off, leaving me only in panties. I had told him a few weeks before that during one of our hookups I was so turned on and hot for him that I would have let him do anal if he had asked (he didn’t) but he said he would keep it in mind. He started playing with my booty a little which is something he normally does because he loves my ass and I’ll admit, it’s pretty nice. He knew I was on my period already, but he slid down my underwear to just underneath my ass cheeks and began touching my asshole, lightly. I’ve done anal play before with a previous boyfriend years ago but we tried anal but it was too painful and I haven’t tried since. He was massaging it and pressing in a little and it felt so good (I can honestly feel my asshole tingling right now re-imagining it) and he moved behind me and I arched my back to provide better access. He spit and used it to lube it up a little, and he began pressing the head of his cock in just slightly, enough for me to tense up but he was super gentle and was purely focused on me and if I was okay. He kept caressing my back and telling me how sexy I was and he pushed in a little bit more which made me moan in pleasure and he was stroking just a tiny bit but it felt so good. He only pushed in when I relaxed and he kept telling me how good it felt and how hot and sexy all of it was which just made me hotter. At this point, I reached my hand in between my legs and began rubbing my clit and he was floored by that and he started to moan more and I was clenching my asshole around his cock because I was close to cumming and when I did it was amazing. I hadn’t had an orgasm like that since I’d done anal play before and I even had a second one less than 2 minutes later. The thing that was so special about this was that I felt so close to him while he was in my ass and it was incredibly intimate. It was such a good feeling. After this, we laid in bed for a while and I gave him a slow handjob which lead to me giving him head, and I kept it going for 35-40 minutes. I know that sounds like torture but when I suck dick I’m in charge and I didn’t want to stop, I love giving him head and could do it for hours. When I made him cum it went straight into my mouth and on my face, and it was amazingly satisfying.

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? We laid in bed for a while and talked, and eventually, I went home and went to bed.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting

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 told my best friend that I had gone but I didn’t give her any details because she’s very vanilla and would think it was gross or something worse.

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

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 closeness I felt with him was amazing and it made me feel even more comfortable with him.

What was the WORST thing about this hookup? The fact that we didn’t have any lube so we couldn’t keep going.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m definitely open to anal sex now, I was a little hesitant before but willing to try with him.

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!