Busting my Casual Sex Cherry with a Black Beauty

by Bigbadandugly

What’s your gender? Man
How old are you? 47
What continent do you live on? North America
What country and/or city do you live in? SF Bay Area
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Legal exec
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Nornal
How many sexual partners have you had in your life (including oral sex)? 21
How many hookup stories have you here posted before? 4

Busting my Casual Sex Cherry with a Black Beauty

How long ago did this hookup happen? SEPT, 2014

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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’s an African American with a very low fat, extremely toned body. about 5’7″ or 5’8″. Was currently working her love as a Samba dancer while in between real jobs. Her skin tone was probably about medium of slightly darker for an AA, but she was tanned due to her jogging. Until she showed me her tan lines, I never new black people tanned! Her boobs were a bit droopy which was the only downside to her stunning body, and she just had a little runway shaved in her pubic area until she shaved that off for me.

I had just moved to a new city in California to start a new job and my company put me up in a brand new, furnished 1 bedroom condo downtown. My spouse was not relocating with me. We were going into the Labor Day weekend, and, knowing I was new in town, a work colleague suggested I check out the Community section in Craigslist for activities to do over the long weekend.

I check it out on Friday night and noticed the “Personals” section and started rifling through a few of the sections. Given I’d only ever been with my wife prior to this, I was shocked at the openness exhibited in the Casual Encounters section. I came across one post with the title “Black Beauty” where a woman was looking for temporary accommodations. Given I had a big apartment, I responded and she responded back immediately. We continued to e-mail each other for the next 20 minutes or so and her story checked out (she said she was doing shows in Sacramento and SF the coming weekend and I checked the Internet and the story checked out.) She was flying out to her parents’ place in Florida in two weeks and needed a place to stay. Ironically, as big as the Bay Area is, she was currently staying in a single room occupancy hotel just a block away!

The next morning I cleaned my place and met her at her place and brought her and her luggage to my place.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Once we got to my place we sat down on the sofa and had a short chat. After a half hour, she mentioned she was dying for a bath since she had been staying in the SRO which only had shared showers. After about 30 minutes she walked out of the washroom stark naked holding a little bottle of body cream and she seductively asked me if I would like to help her apply it on her back.

Having only been with my wife up until now, I was absolutely stunned that this woman was standing naked in front of me! I felt like I was a deer caught in the headlights of an oncoming car! Being as naive as I was, I wasn’t sure if she was initiating sexual interactions or if she legitimately just wanted help applying the cream to her back (like I said, I was extremely naive). Either way, I was willing to please and suggested we go into the bedroom when she could lie down.

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 we got into the bedroom, she lied tummy down on the bed and I started applying the lotion on her back as requested. While doing this, I couldn’t help but ogle at her beautiful ass. After a couple minutes of rubbing cream up her back, I started to work my way down to her waist and the small of her back. At this point I was still uncertain of her intentions, but I decided what the fuck, I’m going to start to apply the lotion on her butt cheeks to see what kind of reaction I got.

To my surprise (and relief), she did not react as my hands started applying the cream to her wonderful ass cheeks. I applied the cream in circular motions before starting to lightly knead her cheeks. All while doing this I am still extremely tense as this is the first naked woman I’ve been with other than my wife. I recall feeling like members of the FBI or Navy SEALs were going to rappel down from the roof of my condo building and smash through the glass windows and take me down!

After kneading her cheeks a bit I built up the nerve to ask her to turn over. After she rolled over I noticed the big grin on her face so I decided it was time to drop the pretense of applying lotion and slowly and gently spread her legs to reveal her sweet, dark pussy lips. She had large inner lips which were already swollen and extending out of her outer lips. With both hands on her thighs holding her legs open, I started licking her lips in a repeating upward motion before taking one of my hands to spread her lips to give me better access to her vaginal opening and her clit. I continue to work her pussy until I stopped for a brief second to rest my tongue and tell her “I have a vasectomy”.

Her response was “Those are the magic words!”

I returned to eating her out until I suddenly heard a long drawn out moan come from her. I continued to eat her out for a bit after her orgasm until I couldn’t stand the intense throbbing of my cock. I climbed aboard her and fucked her like a crazy man until I busted a nut inside her. It was the most intense orgasm I had had in a long time!

My wife had trained me to quickly grab a tissue to capture my jizz leaking out of her immediately after I came in her, so I dutifully did the same with my Black Beauty. She seemed pleasantly surprised at my consideration and voiced her appreciation (later on in life I realized the overwhelming majority of men leave it up to the woman to deal with the dripping jizz).

We laid there and chatted for a bit before cleaning up in the washroom. That evening we had dinner, watched a movie and fucked again.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? She stayed with me for ten days and we fucked 2-3 times a day for the duration (except for the weekend she had to perform her two Samba dances – given the costumes they wear, she didn’t want to have my cum leaking out of her vagina while she had to wear the very revealing but beautiful outfits. We spend many hours together when I wasn’t working, talking about many things. Despite having very little formal education, she was a very worldly woman and was very interesting to talk to.

On the morning she left I rented a car to drive her to the airport and gave her $200 for the trip as she was dead broke and I felt her luggage was soooo heavy I felt she would be paying an overweight luggage fee. I dropped the car off at the rental agency and walked to work. When I returned to the condo at the end of the day it felt so empty without her or her stuff there. It was such a great ten day period that I literally cried when I got back to the empty apartment.

I have not seen her since that day, but we text and e-mail every three months or so.

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, Thought it was an important experience to have, I was feeling lonely

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? A little bit

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? My two former work colleagues and two women I recently met in California that I talk openly with.

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 sex with only the second woman in my life, and having the shot fling last ten days

What was the WORST thing about this hookup? That she had to fly out to Florida to end things

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I popped my casual sex cherry with this lady. It dispelled any notion I may have had that casual sex is bad, and has opened the door to much more casual sex over the past 3.5 years,

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!