What’s your gender? Woman
How old are you? 39
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Ontario, Canada
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Massage Therapist
What’s your current relationship status? Dating casually
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? Heteroflexible
How many sexual partners have you had in your life (including oral sex)? 17
How many hookup stories have you here posted before? None
Fill Me Up Before You Go
How long ago did this hookup happen? 2 days ago
What was your relationship status at the time? Dating casually
How would you best classify this hookup? Friends-with-benefits
How long did you know the person before this hookup? For less than 6 months
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? Neil (fake name) and I met a few months ago upon the suggestion of a mutual friend. She thought we would get along beautifully and be well suited as sexual partners. She was right. We’ve been creating a friendship and mutual trust alongside a steamy sexual relationship for a few months. Neil is so handsome; he’s quick to smile, has beautifully shaped lips, dark brown laughing eyes, soft and smooth dark brown skin, has big strong hands with the most divine fingernails, is just shy of 6′ and well built/muscular/fit, and has the loveliest little round ass. I have the highest regard for Neil because he’s always so great with every person he interacts with. This alone makes him one of the sexiest men I know, then add on his joie de vive and his utter enthusiasm for everything.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? This experience began with a planned date the night before. It had easily been a couple of weeks since we saw each other and were eager to feast on one another as much as possible. Neil let me know that he would have to leave around 9 am to attend to work and clients.
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? Around 8:45 am we were lying side by side in my bed, on our backs, lamenting how he had to leave. I said “one of these days I’m going to ask you to stay all day so that we can play with each other for a full 24 hours.” The thought of this alone began to turn me on, so I turned to Neil and said “before you go I need you to do one thing.” He asked me what. I moved my face down to his semi-hard penis and spit on it. He looked at me curiously but his willingness was apparent when his cock grew hard.
Neil has a beautiful cock. As a side note, the first time I saw it I was worried he wouldn’t fit inside me. He’s above average in length by a couple of inches at least, but above average in girth by a lot…all the way tip to hilt. I’m a petite woman with a smaller pelvis.
Getting back to the story, Neil’s cock was hard and the tip covered in my spit. I straddled him, slid him deep inside my pussy and said “I want you to cum inside me, fill me up before you leave, and leave me with your cum in me.” I started riding him, first slowly, then faster. The look on his face was pure pleasure and excitement. I could tell he was turned on by my request. Especially since the night before I shared with him that one of my kinks is being filled up by a man. He was stroking my hair, my breasts, my ass, and watching me fuck him. He said “you’ve taken me all in, every inch.” Feeling him inside me, hitting my cervix was making me even wetter. Then he grabbed my hips and began to control the rate and depth. I felt his cock swell even larger inside my pussy. He said “turn over” and physically turned me, positioning me on my belly with my legs straight and my face pressed into the bed. He lifted my ass up enough that he could slide his engorged dick back inside my cunt, saying he just loves the sensation of my ass pressing into his abdomen in this position. He then plunged in and out, deeply, gaining in momentum until his enormous cock began to pulse. He came long and hard, moaning and quivering for over a minute, filling me up with his ejaculate.
How sexually satisfying was this hookup? Very
Did you have an orgasm? No, but I was close
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 snuggled for a moment afterwards but he really had to leave. He got up from bed, started collecting himself, and went to the washroom to clean up. While he was there I began rubbing my clit and fingering the wetness of Neil’s cum. I hadn’t orgasmed while we fucked and I knew I’d finish myself off once he left. He returned to the bedroom, got dressed, and kissed me goodbye. He admired my exposed pussy, as I was lying supine on the bed, uncovered and spread open. If I could have put a plug in myself to hold all of his cum I would have. I got up to let him out and returned to my bed, grabbing my dildo and vibrator along the way.
When I slid my dildo inside my pussy I was excited at how slippery I was. I turned on my vibrator and rubbed my clit while fucking myself with my dildo. I wanted to shove Neil’s cum back up inside me as deep as I could go. With increasing intensity and speed I came hard, cumming all over the dildo, totally spent.
I am thoroughly enjoying my time with Neil. For however long we play this game of lovers, I expect it will be hot, steamy, and a lot of fun.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization
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? To the mutual friend who set me up with Neil. She’s one of my best friends. She was so thrilled to hear of my pleasure and my new willingness to make a request like I did.
How would you best summarize people’s reactions about this hookup? Relatively positive
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? Having Neil be able and willing to fulfill my request and leave me full of cum.
What was the WORST thing about this hookup? He had to leave and I would have loved to have him shoot another load in me. I love love love watching, hearing, feeling him orgasm.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This experience was another step in my quest for my own freedom in sexuality and expression. I practiced sharing a kinky desire and asking for it, all skills I am finally employing after being prudish earlier in my sexual life.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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’m becoming more and more comfortable with casual sex. I was raised to believe it was wrong, which is silly. What I’d like to see is great safer sex education on a mass scale, and the removal of the stigma of shame surrounding casual sex. Sex is normal, and fun, and something we’re wired for and not everyone is suited to a life of monogamy in sexual partners. Casual sex is the cure for curiosity, exploration, needs being met, connection, and so much more.
What do you think about the Casual Sex Project? I have loved this project/site ever since I discovered it about a year ago. These stories are one thing I turn to for erotic pleasure, knowing the contributors are real people out living their lives.
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