by homealonewithasmartphone

Gender: Male
Age: 28
Race/ethnicity: Blatino (Black/Latino)
Current location: New York, NY
Highest education received: College degree (eg., BA, BS)
Occupation: Banker
Relationship status: Married
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 25
How many hookup stories have you here posted before? 0

Dick Pics And iPad Cameras

How long ago did this hookup happen? 2 weeks ago

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…)? One-night stand

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? Black girl, late 20s to early 30s, 5″2′ 125 lbs c-cup breasts curvy brown bottom mostly flat tummy, permed shoulder length hair, glasses, super cute face, no tattoos, belly button piercing. We never met before. She answered my ad on CL. The ad contained a picture of my dick. Yes dick pics work. I was incredibly nervous and skeptical prior to meeting her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I posted the ad on CL around 7pm. She replied to my ad at 10:30. This hook-up did NOT take place in NY so my ad was probably still on page 1 of m4w casual encounters. She sent 3 nude photos that did not include her face. She asked for my face pic and another dick pic which I obliged. We emailed/texted back and forth for an hour before speaking on the phone…
Her: Hi how are you?
Me: I’m good just a little tired
Her: Well I’m a swinger so if you’re too tired we can reschedule
Me: wha??
Her: I know sometimes guys can’t perform if they have something on their mind or if they’re tired. Don’t come over if your dick don’t work. 
Me: Don’t worry that won’t be a problem. I’ll be on my way over soon.
I showered and took a $50 cab via uber to her hotel that was 40 min away in no traffic. I chugged a red bull and knocked on her door at 12:40.

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 answered the door in a towel and I was just blown away. Her body looked way better in person and her face was very pretty. She had soft r&b playing on her iPhone…and she had a web cam connected to her iPad that was pointed at the bed.
Me: (staring in bewilderment) what is that? 
Her: (laughing) like I said I am a swinger and normally my boyfriend is here with me but he’s 500 miles away so he wants to watch on cam. Are you down?
I looked closely at the iPad screen and I saw a shirtless bald black guy in a dark room with his shirt off. He looked to be in his 40’s and he was taking pictures of the screen with his phone. I couldn’t fucking believe it. After I laughed the last of my nervousness out I agreed and took off my clothes.
I sat the edge of the bed and she stroked my cock while standing in front of me. I squeezed her ass and kissed her breast and body. She made her rules clear before I came over: no kissing on the mouth, no anal and if I want a bj from her I have to bring flavored condoms. The stupid gas station by my hotel didn’t have any of those. She looked really good and she smelled good too. I complimented her non-stop as I enjoyed her body. I just couldn’t believe her boyfriend was cool with this shit. I also felt a ton of pressure to perform since her boyfriend was watching us on camera but I still managed to get hard despite that and no blowjob.
She agreed to ride on top first and she was just great. She was the perfect mix of baby fat and toned muscle. I asked her to lean in towards me and I started to pound it from the bottom. Her boyfriend yelled at me “yea nigga fuck that pussy!”. Weird. We later switched to missionary and then to my disappointment I came. I must have lasted a good 15 minutes and she made it clear she was ready for round two. 
I usually don’t cum this fast and most of the women I’ve been with don’t have the energy to go a second round. I honestly don’t know how much time I need to get hard a second time. I explained this fact to her and her swinger lifestyle started to show itself. She was calm and patient with me as we spoke about things like traveling for work and etc. I asked her how she got introduced to being a swinger and she told me that she and her boyfriend have been “playing” for 2-3 years now. The whole concept of it is alien to me really.
I got hard again and we started missionary and things were going great but then her boyfriend started yelling into the camera. “Babe….BABE!! You’re not at the angle we discussed.” She did her best to remain calm and patient as they semi-yelling at each other back and forth. I started laughing hysterically and lost my erection. She then told him to please be quiet so I can focus.
At this point I could tell her patience was starting to wane. I looked her in the eyes and said “I’ll fuck you good, I promise”. She let out an exasperated sigh and said “please, thank you. I’m doing this for myself, I’m not worried about that nigga right now.”
The third time was the charm and we went at it for a good hour with minimal talking. At one point my dick actually went a bit numb inside the condom which made me worried as I could not tell the fullness of my erection without looking at it. I gave her every ounce of energy and strength and I had and she took it like a champ. In missionary she would let her hands and eyes wander around my body as  I went to work which was great for my ego. At one point she did a full split and arched her pelvis upward. I’ve seen this in 100s of pornos and here it was right in front of me and I didn’t even know what to do with it.
My body was dripping with sweat by the time I realized my dick has no idea what’s going on. Her boyfriend actually fell asleep and missed all of round 3. As I dried myself with a towel they spoke:
Him: that nigga was wack
Her: No hunny he was good. He did a good job.
Him: whatever he didn’t do shit. He was mad fucking boring. I’m going to bed
Her: Ok hunny. Goodnight, I love you.
She turned to me explained he’s drunk. I remarked he could always go back and watch it later and she explained that they weren’t recording it. She said this with no hesitation so I believe her. I put my clothes on, thanked her for everything and wished her a good night. It was after 2am and I had to be at work 8am. I waited in the hotel lobby and watched the news for about 20 min as I waited for my ride from Uber to show up. I didn’t go to sleep until 4am.

Did you have an orgasm? Did your partner(s)? I had one, she had multiple.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We did not discuss STI history. We used condoms all three times.

What were your REASONS for having this hookup? The sex life in my marriage is damn near dead.

Were alcohol or drugs involved? If so, how much? No.

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 e-mailed her the next day thanking her yet again. I told her it was the best and most bizarre experience of my life (which is true). I gave her my e-mail and told her to please contact me if she’s ever in NYC. She replied and said she had a great time as well and that she’ll look me up if she’s ever in NYC.
In about a month or so I think I’ll send her a follow up e-mail just to wish her well and to remind her to keep my e-mail on file. I doubt I’ll ever see her again but who knows?

To whom did you talk about the hookup? How did they react? I told my big brother. He enjoyed hearing about it.

Was this a consensual and/or wanted experience for you? For your partner? We both wanted it.

Do you regret this hookup? If so, why? Not a damn bit.

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 thing about this hookup was her. She is the most competent sexual partner I’ve ever had despite her rules (no oral and no kissing). 
The worst thing is not feeling like I’m not in control of my erection as much as I would like to be. Had there been another subtle negative element added to the mix it’s possible I would not have been able to perform after round 1.
I am now open to having sex with a woman as people watch on camera. I’m not open to threesomes with 2 men and 1 girl or having a man in the room observing us. I feel like I did ok and that there’s room for improvement on my part. My workouts are now more focused than they were before.

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

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

Anything else you want to add about this hookup or anything else? Posting in CL casual encounters is a crap shoot. Most of the time I do not get any responses. I know I’ll never get this lucky in life ever again.

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