A Friendly Shoulder to Cry On

by Cee

What’s your gender? Man
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Some college (not currently in college)
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)? 15
How many hookup stories have you here posted before? 3

A friendly shoulder to cry on

How long ago did this hookup happen? 1 week

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

How would you best classify this hookup? First of many

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? She had light brown hair, blue eyes and was very cute, about 5’3″. Average weight, maybe a few extra pounds, she had great legs for her short size and an alright bum, a little flat but still good. Her breasts were amazing, nice full C cups. She was my friend’s ex-girlfriend, but we had become pretty good friends and so we still kept in contact. We had previously had a drunken heat of the moment hook-up about 6 months prior that, but neither of us brought it up after it happened. Despite being my friends ex, I definitely had a thing for her. There was just something about her…she had that innocent girl next door good girl personality with a kinky sexual side.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had been texting all day and I could tell she was still in a slump from the breakup. I asked if she wanted to hangout that night, but she turned me down at first but later changed her mind.

She came over with a bottle of wine and we played some board games while talking and finally sat back for a movie. She was a few glasses of wine in and I was a few beers in, when she grabbed a blanket and snuggled up to me. We couldn’t have been any more than 10 minutes into the movie when she surprised me with a kiss. I returned the kiss and we made out for a bit. I wasn’t sure what to think of it but didn’t really care. Finally she broke the kiss and came right out and told me she hadn’t had sex in over a month, and she was insanely horny and seeing as we had hooked up before there wouldn’t be any of that first time awkwardness.

There was a little hesitation in the back of my mind because she was my friends ex but having a beautiful horny woman in my lap made the decision a little easier. We started making out wildly as we undressed each other, and thanks to her workout routine she looked even better this time around.

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? She was so horny that we didn’t spend much time on foreplay. She was grinding against my cock as we made out and she got lined up to take me when I stopped her and told her I’d grab a condom and she just smiled and said “You don’t have to, I’m still on the pill, and I’m single now.” I just smiled and grabbed her hips and pushed her onto my cock. As she rode me for her own pleasure, I sucked and nibbled on her beautiful tits, and her pussy felt amazing. It was incredibly wet, hot and tight, and luckily she rode me for a while at a pace where I was able to hold off.

She eventually needed more and told me she wanted to be man handled and fucked really hard, and I was happy to oblige. I tossed her down on the couch, put her legs on my shoulders and and fucked her hard and deep. I could feel her bottoming out but she pleaded for me to continue. Then her next request totally caught me of guard — she told me to choke her while I fucked her, but I was unsure but she insisted saying it made her orgasms better.

I grabbed her throat lightly as I fucked her, and she instructed me to get tighter and I found myself strangely aroused. I knew I was close so I pulled out in order to prolong things for a while and we made out for a a bit but soon she was begging for me to fuck her again. I bent her over the arm of the couch and started fucking, I pulled her hair and drove my cock as hard and deep as I could as she rubbed her clit. Soon she was incoherent as she began to moan and scream before losing all control and was a mess. I couldn’t take it any more and erupted inside of her. It felt so good I didn’t want to pull out but we both eventually fell to the floor where we caught our breathe and talked some more. She asked if she could spend the night and I knew that meant we would end up fucking all night so obviously I was okay with it.

In the past on a couple occasions, my friend had made comments about her being wild in bed and liking rough stuff but until that night I never really believed it. That night she let me fuck her as hard as I could, she begged to be choked and have her hair pulled, and she deep throated me until she was gagging.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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 felt great the next day especially since it started with her handling my morning wood with a blowjob. I don’t really have any hopes or expectations, feels kind of shitty cause its a friends ex, but we did talk and we both are sexually attracted to each other and she said she isn’t ready for a relationship this soon but when she has needs to be met she would rather get fucked by me than randoms, which is something we have agreed to keep quiet about. She certainly isn’t the innocent good girl I thought she was.

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, Attraction to partner(s), Emotional intimacy, closeness, connection, Intoxication, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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

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? Somewhat

Why do you regret this hookup? friends ex, the sex is great but that’s all it will be

What was the BEST thing about this hookup? her level of surprising kinkiness

What was the WORST thing about this hookup? nothing

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

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

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