by Craig

Gender: Male
Age: 37
Race/ethnicity: Caucasian
Current location: CA
Highest education received: College degree (eg., BA, BS)
Occupation: Information Technology
Relationship status: In a relationship
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 60
How many hookup stories have you here posted before? 0

Surprise Visitor

How long ago did this hookup happen? 2 months

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Fuck Buddies

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? Riley is a gorgeous brunette, 30, 5’10”, large D cup breasts and legs for days
Stephen is 6’2″, 42, 8″ cock and trim
I met Riley a few months before.  She contacted me on Fetlife and asked that I train her to be the perfect submissive slut.  She was so stunningly beautiful and eager to please it was impossible to refuse.  We had many training sessions before this and felt it was time to push her boundaries a bit.
I met Stephen a few years before and knew of his interest in group sex.  Recruiting him for the occasion was not difficult.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? During our negotiations, Riley and I discussed her desire for group sex, particularly DP and DV.  This was something she had never tried. Once we had built a level of trust I decided to push her boundaries and show her off to my friend.
I planned a session with her as usual but didn’t tell her of my intention to have a threesome.  Stephen was to arrive at my house 15 minutes before and stay out of sight.

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? Once Riley arrived, I had her strip naked, put on her collar and get on her knees.  I blindfolded her while she was sucking my cock and turned up the music to muffle any sounds.  Then I instructed her to wait and I left to grab Stephen from the other room.  I whispered in her ear that I had a surprise and for her to open her mouth.   Much to her astonishment, Stephen then fed her his cock.  I removed the blindfold and we took turns fucking her face, sometimes forcing both of us into her mouth at once.  I noticed Riley was literally dripping wet and I figured it was time to give her some pleasure too.  I slid underneath her and licked her pussy while he fucked her face.  It was an amazing view!  Then she started riding me and Stephen eased into her ass.  Riley instantly had what she described as the most powerful orgasm of her life.  We tried various DP positions and then got into my favorite -King of Clubs. She sucked us both in this position and crouched over us and put both our cocks in her tight pussy.  What a feeling!
We ended the encounter with a huge double facial.  She was completely covered with cum and looked like the most happy and beautiful girl I had ever seen.

Did you have an orgasm? Did your partner(s)? I had a huge orgasm as did Stephen.  We lost count of Riley’s orgasms, but it was well over 5.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Riley and I had STI screens well before any sexual activity.  We thoroughly discussed our history beforehand as well.  Stephen also produced a recent STI screen to me.

What were your REASONS for having this hookup? There were many reasons.  I like group sex. I also wanted to introduce Riley to double penetration and to give her a safe and exciting experience.

Were alcohol or drugs involved? If so, how much? None

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I still have sessions with Riley.  Since this occasion I have also set up a gangbang for her and accompanied her to an orgy.
I am very fond of her as her trainee and have only had the best experiences with her.  One day I will have to set her loose and hopefully I can find her a good Dom who will treat her well.  I will always look back on these times fondly.

To whom did you talk about the hookup? How did they react? I’ve told two other girls I am training.  I’ve asked them to contact her as a reference to my reliability and ability.  They reacted positively and wanted a similar experience.

Was this a consensual and/or wanted experience for you? For your partner? This was consensual for both of us and was discussed in our negotiations.

Do you regret this hookup? If so, why? No

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best part of this experience was watching her have the orgasm during DP.  She shook violently and broke out into a sweat because of the intensity.
This hasn’t changed me or my viewpoint at all, but I think she has been changed forever.

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

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

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