The Sleepover Pt. 01

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A night out leads to new experiences with old friends.
6.1k words
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Part 1 of the 2 part series

Updated 06/08/2023
Created 03/19/2017
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I am a married black man, early 50's. This is my story; a reminiscence of real thoughts, feelings and events of my life. My decision to write it was born out of a private personal need for erotic expression - an outlet for sexual frustration. My decision to share it is an extension of that expression, but not an invitation for anyone else to use it in whole or in part without permission. By the way, my name is NOT Roy Williams, nor are Rick and Tammy my old friends' real names, for obvious reasons. But hey, you can call me Roy if you like. Thanks for reading.

*****

PART 1

Chapters 1 - 5

Chapter 1

Sexual Self-Assessment

In the first two years after my divorce I had a few hook-ups, a few girlfriends, nothing serious though. The frequency of sex was fairly regular, unlike it had been in my marriage, and the sex was pretty good most of the time, also unlike my marriage. Experimentation and eroticism, although somewhat limited, slowly became a part of my sex life, and liked it.

My job involved a great deal of pressure and stress, so the unwinding that came with sex was a mental and physical necessity. As a mid-thirties black man, highly energetic, educated and professional, fit and attractive with light tan skin and a rock hard 7.5-inch circumcised cock at the ready, I was rarely long between women, or the occasional adventurous couple. Although I enjoyed the hook-ups and booty calls (after all who doesn't like a casual fuck), the sex became somewhat routine and lacked variety. I wouldn't say I was sexually bored by any means, just less than content.

In general, I found the black community to be homophobic, condemning and quick to label a man as either straight or gay; one or the other. There were various historical, cultural and religious reasons for this, but regardless, failure to express extreme disgust and physical repulsion to any sexual contact between men was cause to be socially condemned as gay, and possibly an outcast.

The absolute worst thing to be was on the down-low or DL. Then you were not only gay, you were a liar as well. Even being raised Catholic, I have never encountered more animosity, guilt and condemnation about any social or sexual issue as that of the stigma of the DL 'gay' black man. It was for me, however, only a passing thought at that time and of no real consequence because I was absolutely NOT gay; I loved sex with women of all shapes, sizes and races. In fact I had, and have to this day, a particular sexual attraction to good-looking full-figured women; women with more of everything that makes a woman a woman physically.

I explain that, so that you may understand the internal conflict I experienced when I discovered that I was not disgusted or repulsed to be naked in the presence of the husbands of the few couples I had the opportunity to play with. Three of the couples were my age, two were older. One of the older guys would remain clothed; focused only on the cuckold experience of watching his wife with another man - especially a younger black man. Other guys would get partially or completely naked, either masturbating off to the side, or taking turns with me fucking or getting sucked by their wives. Usually this happened in a tag team fashion with one of us moving completely aside before the other would join in with the wife. In a few instances, we would play with the wife simultaneously - me eating or fucking her while she was sucking him, or vice versa - her reverse cowgirl grinding my cock while she sucked him, or vice versa - you get the picture.

On a handful of occasions, the imaginary 'straight' line was crossed in the heat of the encounter. For instance:

- While rubbing, caressing or squeezing her body, ass or tits, my hands would touch the husband's hand or body

- While switching positions in close quarters, one or both of our cocks would momentarily touch the body or a leg or arm of the other guy

- While alternately sucking both of us, she would allow our cock heads to rub together when switching back and forth

- While one of us was fucking her missionary style, face to face, she would alternate between kissing him and sucking the other's cock in close proximity

- While engaging in double penetration, there was an occasional touching of condomed cocks, and an almost unavoidable rubbing of balls

- And once, during a particularly energetic cowgirl fuck with a deliciously plump wife, she was leaning far forward with her huge breasts swaying above my face, supporting herself while holding my wrists above my head, when my cock popped out of her pussy. I felt a hand guide it quickly back in place, and she continued furiously rocking back and forth, up and down without missing a beat, still holding my wrists. Whether I was hypnotized by the swinging of those beautiful tits, or overwhelmed with the feeling of her soft ample body desperately working itself to orgasm on top of me, I didn't give it a second thought.

When these things happened, I felt no repulsion. If my cock was already hard, it did not go limp. If my cock was soft or semi-erect, it would stiffen. It was a bit awkward at times, but I actually found it arousing in the context of the entire experience. In the strict world of straight or gay, that would be considered gay. But I wasn't. So, what the hell was I?

I went in search of an answer to my dilemma where else? - the internet. The articles, blogs and commentaries of so-called 'experts' were useless and contradictory. But the erotica served to at least provide some context to my evolving sexual interests. Straight porn was hot, in all its common forms. Some fetish porn aroused me, and some absolutely didn't - no surprise there, that's why they are called fetishes. I found gay porn of no real interest, and man to man romantic kissing, and emotional affection or intimacy were sure turn-offs.

Bisexual porn however, was particularly arousing. Both FFM and MMF threesomes were hot, as was group sex with bi activity. Even MM with the two men focused more on the 'act' than each other held some erotic interest for me. In general, I enjoyed my sexual self-assessment research. Between the internet sites and the adult cable TV channel movies I watched, I began to subconsciously classify the various sex acts as one of three categories: Naughty, Kinky, or Nasty.

Naughty involved mainly heterosexual activities with incidental, or limited intentional bi contact between women or men, all playing at the same time. Massages, caressing, rubbing, tickling, teasing, hand jobs, etc.

Kinky involved situations with bi activities that were overtly intentional, and done for the specific purpose of satisfying the erotic physical desire of one or both same-sex partners in the threesome (or more-some). Body contact, embracing, light bondage, wrestling, pinching, spanking, genital frottage, oral contact, licking, sucking, etc.

Nasty involved uninhibited bisexual contact between two (or more) same-sex partners, involving activities similar to heterosexual sex, driven by the intense or insatiable need for sexual gratification. Nasty was lust-driven and wanton, and either without any consideration at all of gender, or very purposefully focused on the same-sex aspect of the interaction. Full-on hand jobs or blow jobs to completion, orgasms, cum, D/s, BDSM, toys, digital penetration, humping, grinding, fucking - you get the idea. Nasty had few limitations.

I was only in the fantasy stage of my interests, without much serious thought about actually doing anything. I considered 'Naughty' to be tame enough to consider someday, maybe, given the right circumstance. What the 'right circumstance' was, I had no idea; but I knew it was definitely a long shot.

During one of my research sessions, I was surfing through erotica, straight and bi content mostly, when a string of links led me to a local personal ad for a bisexual couple. I clicked the ad link and a second later I found myself staring at a photo of my former brother-in-law and his new fiancé.

"Holy shit!"

Chapter 2

The Long Shot Right Circumstance

"Holy shit!"

I said it out loud a second time to myself as I sat there with my mouth open studying the photo of the couple on the screen. They had discreetly blurred their faces, and their background was fairly generic. I suppose that would have been adequately anonymous for any viewer other than me. But I had helped them do work on their house and helped them move in, so I was familiar with the room and the furniture. I also recognized my housewarming gift to them on a shelf behind them. I deliberately backed out of the browser and then carefully retraced my steps to be sure that I really saw what I thought that I had seen. Once again, the very same picture filled my screen. There was no doubt about it; that was Rick and Tammy.

I had known Rick for over ten years at that point. We first met when we were each engaged to a pair of sisters at the same time. He got married first, then me. We had the usual brother-in-law relationship: interacting at family gatherings, watching sports, engaging in friendly competition on the basketball court, touch football field or in the pool hall. And we eventually connected on another level while bitching and complaining to each other about our own and each other's wives. Years later he was the first to get a divorce. He introduced Tammy as his girlfriend a year or so after his divorce was final, and before long, they were engaged.

Rick was five years younger than me, white, with brown hair worn in a somewhat preppy style, blue eyes, trim and a decent athlete. Not a pretty boy, but admittedly handsome. I had stayed in shape, and had no trouble keeping up with him, except at 6'1" tall with his extensive basketball background, he kicked my 5'8" butt up and down the court whenever he got the chance. Tammy was a 5'5" green-eyed brunette knockout with perky medium sized tits and a perfectly rounded ass. Her face was truly stunning, with flawless skin framed by her shoulder length dark hair, killer smile and full sexy Angelina Jolie lips. I came to look forward to the cordial brief embrace and peck on the cheek from her when we'd all see each other every few months or so. Rick was a lucky man, and he appeared to know it judging from the smirk he always gave me each time I mouthed the word "Wow!" after greeting his hot fiancé.

There they were, on the internet, the two of them; Tammy in a matching black silk and lace bra and panties, and Rick bare chested in a pair of snug navy blue briefs. I could picture in my mind Tammy's full sexy lips behind the blur that covered her face, and I could clearly see that I never appreciated the true size and shape of her tits, even though I had seen her in a swimsuit on occasion. The silky black undercups of her bra looked full and heavy, and cast a healthy shadow just above her pale flat tummy. Her panties traced the flare of her hips on either side of the perfect ass I knew was hidden behind her. The photo cut off at her hips, about the same level as Rick's mid-thigh just to her left. His lean muscled legs contrasted the dark blue briefs, and I could see the outline and bulge of his semi-hard dick laying to one side, trapped by the fabric. Rick's torso and chest were well-formed with good muscle tone and minimal hair. Behind the blur covering his face I knew he was wearing that same damn smirk he'd give me whenever I drooled over Tammy.

So, Rick and Tammy had a secret. Now what? I could just keep this to myself. That would be easiest; no drama. But it would be unbearably awkward the next time we met. I could just come out and tell them I knew their secret. But that would give away the fact that I was online looking at such things, and the embarrassment on both sides might damage our friendship.

The fact was, Rick was a long-time friend who I just discovered was "newly bi" as his profile described, which just so happened to be my new area of curiosity. On top of that, his sexuality was accepted and apparently encouraged by his fiancé, who listed herself as an "experienced bisexual woman." I liked Tammy, and I was attracted to her in a half platonic, half lustful way, but always respectful of her relationship with Rick. If there ever was a long shot 'right circumstance,' this might be it. I just had to figure out what to do next without screwing everything up.

Face to face was no good. Too awkward. A text or phone call would require a response - too confrontational, so that was out. And formally responding to their ad through the personals site was no good. Too weird and impersonal. So, I decided that a plain old email to Rick was the way to go. It took me three drafts, and a day of second guessing and sitting on it without hitting [SEND] ... but I finally did it.

SUBJECT: Keep This Between Us

Hey Rick, how's it going?

Man, I've got something to tell you, but I need to start out with a condition. Here's the deal: If you never mention this email again, then neither will I. We can carry on like I never wrote it. I want you to know that I'm cool either way, and I consider us friends no matter what.

So, here goes. I saw you and Tammy's profiles and personal ad online. I've recently been surfing some bisexual stuff online, and I ran across it unintentionally. Well, I did intend to surf bi stuff, just not find your ad; You know what I mean. Nice pic by the way! ;-)

So, there you have it. I was surprised; probably about as surprised as you are reading this email right now and me telling you I've got some curiosities of my own. Obviously, Tammy is included in "Between Us" if you choose to share this, but no one else for obvious reasons. Just know that I am good with however you two want to deal with me knowing.

I hope this isn't too awkward. Take care man.

Roy

I must have checked my email a dozen times that night; nothing. I checked multiple times a day for a while; nothing. Had I blown it? Were they just being private? Did I cross a line? Was there a 'bro-code' for this type of thing that I violated? Shit! Damnit! Nothing. Two months of absolute silence. I didn't dare follow up, didn't text, and certainly didn't call. This was bad.

Then, finally, a response. It was a pretty generic email like many Rick had sent me before.

Hey Roy,

Nice to hear from you(blah, blah, blah...) long time no see, what's new? (yada, yada, yada...)Hey, we should get together sometime, you me and Tam. We can hit a bar and I can kick your ass at pool.

Let us know. Talk to you soon.

Rick

There was no mention of my email. No acknowledgement at all about the whole bisexual personal ad thing. Not a word. But then I remembered, I had given him an out. The deal was if he did not bring it up, which he didn't, then neither would I. I re-read the entire email to make sure I didn't miss anything. I hadn't. So, that was that. I had been nervous, and now I was both relieved and disappointed at the same time. It seemed we were still friends and he wanted to get together, so at least that was a good thing.

Then something, subtle but obvious, occurred to me that started the nervous butterflies again. It was not anything Rick had written in his email, but the fact that he had replied directly to my original email without deleting my original message, leaving the title of his response "Re: Keep This Between Us" He could have easily changed it, or simply written a separate new email. But he didn't. I kept that in mind as I responded to his invitation and traded follow up text messages setting up our night out a week later, all the while honoring the deal not to make mention of 'you know what.'

Chapter 3

Date Night

We ended up settling on Friday night. Rick said that he and Tammy had not had a date night in a while, and asked if I would mind driving. Tammy's mom was visiting and was going to babysit, and they both wanted to go out, drink and have some fun. Rick knew I didn't drink, so if the two of them wanted to let loose for a night, it was a logical choice that I should drive. We lived about 45 minutes apart, but it would be good to see them again, and certainly worth the drive to catch up and have some fun out socializing.

I figured I'd swing by their house and pick them up early in the evening. I had not seen their kids in several months, and I had only met Tammy's mother, Samantha, once at their engagement party. She was a very attractive middle-aged fuller-figured version of Tammy; kind of my type. I remembered her to be quite the flirt and insisted on me escorting her around on my arm and dancing with me several times during the party. I teased Rick that it was too bad that she was stuck babysitting and couldn't join us for a double date. He called me a dirty-minded bastard and we confirmed a pick-up time.

Midafternoon on Friday, I got a text message from Tammy

"Hi Roy. Sorry for the late notice, but change of plans for tonight. I need to check with Rick, but I'll text you back later."

I wondered what that was about. We were all divorced parents with shared custody with exes, so kid issues were the usual culprit with things like this. I hoped everything was ok. That evening I got another text from Tammy.

"Don't bother driving all the way to our place."

"Well shit, that sucks," I thought. But a second later another line of text came through.

"We're heading your way. There's a new place not far from you that we REALLY want to check out. We'll park at your place and you can drive us. XOXO."

A half hour later, they were at my apartment door. A handshake from Rick, and that hug and peck on the cheek from Tammy that I'd been waiting for, and we jumped in my car and headed out. The place they picked had a sports bar theme, and it was huge. Screens everywhere, two bars, dining area, darts, pool, shuffleboard, diverse group of patrons but not over-crowded ... this was a good choice. I got a wristband as a designated driver, and the bar policy was that I would not be served or drink alcohol, but my non-alcoholic drinks and all appetizers were on the house. I liked this place, it was definitely a good choice.

We sat, ate, talked, threw a few darts and then moved to a standing table near the pool tables. Rick and I looked like brothers from another mother both wearing blue jeans and polo shirts. Both of us were underdressed compared to Tammy, who wore a silky sleeveless off-white blouse, which draped down diagonally from each shoulder across her breasts, leaving a deep "V" of cleavage. Her ass-hugging black leather skirt was stylish, and a bit scandalous whenever she bent over to reach for a shot at the pool table. As she walked around in her black heels that made her calves flex and her hips sway, she certainly had the attention of every guy near our area. Rick seemed to enjoy the attention Tammy was getting. She would shoot her turn, chat, flirt with a guy or two, sometimes with a girl, and every so often walk over and give Rick a peck on the lips for 'luck', then go back to playing and flirting again. Rick had that tell-tale smirk on his face and Tammy was eating it up. They were having fun, and I was having fun watching them.

After a couple of beers, Rick excused himself to the restroom. Tammy was lining up a shot when one her flirt buddies decided to make a sly move and came up close behind her, placing his hands on her waist with the pretense of helping her. She didn't pull away, and she didn't jab him with the cue as I expected. She was feminine, but she could pack a punch if provoked. Instead, she intentionally pushed her ass firmly back against him and wriggled a little bit as she leaned in for the shot. She turned her head, looked back the guy, and made a perfect no-look shot, sinking the ball easily.

"Nice!" "Whoa!" "Yeah baby!" The compliments erupted from her new admirers around the table. Tammy casually straightened up and walked around the table for her next shot, leaving the surprised 'Mr. Sly' standing there with an obvious instant hard-on in his pants and a grin on his face. Two easy shots and a miss later, Tammy stepped over to our high-top table, took a swig of her beer, and turned to give Rick a kiss.

12