Denver, Colorado
Twelve years ago

At 25, I believed myself invincible and couldn’t believe my luck when I met an 18-year-old high school cheerleader. I’m talking super petite, five feet, with small tits, a thin waist, and a tight, tiny round ass. As you’d expect, it displeased her parents when she dated a man as old as I was.

We promised her folks we wouldn’t make love until she’d graduated high school. We knew the promise would be hard to keep, but we’re determined to stay strong. Still, doubts lingered about whether I’d taken on too much with this task. My girlfriend, Cyndi, however, had no reservations. She assured me I wouldn’t be fucking her. Despite her determination, after a month or two, we made do with mutual oral sex. When she was on her period, she sucked me off. And, notwithstanding my love for her, I fucked other girls because I can be a hound dog.

When I met Cyndi, recognizing she was the boss didn’t take long. Her casual demeanor, often cruel jokes and belittling comments, sometimes her attitude actually scared me. She’d be kind and funny, but in a flash, Cyndi would do something wicked, say or do something without considering the consequences of her words. I realized she had a certain spontaneous callousness, which she didn’t intend to hurt, but was, in fact, quite dreadfully painful.

When she first touched my penis, it brought up feelings inside me. Emotions I couldn’t explain — a mixture of anticipation and fear. It wasn’t what I expected, yet I wanted more. As she caressed my small dingus, my body suddenly turned icy.

While I wanted her attention, at what price did it come? How could I keep my distance, keep our promise to her parents while yearning for her touch? Out of nowhere, she blurted out the cruelest comment while rubbing, stroking, and exciting me.

“Goodness, I thought you’d be bigger,” she said, shrugging her shoulders. “Beggars can’t be choosers.” In a matter of days, she made no less than 30 comments about wishing I was more of a man where it counted than I was.

One night, in my car, parked at our favorite make-out spot, other than my apartment, once she got me off, she cut me to the quick.

“It isn’t very cool that I can get your entire dick and balls in my mouth. I’m not sure you’ll even break my cherry when we fuck. I guess as long as you get me off with your tongue will be good.”

Tears burst from my eyes, and I blabbered, “If you want to break up, I understand.”

“Don’t be a fucking baby,” she said. “I don’t want to break up. Damn, Jeffery, you’re a pain in my rump. I love you, and that means something. I’ll put up with your shortcomings just like you’ll put up with mine. Don’t be so thin-skinned.”

“I’m sorry.”

“Stop it,” she said. “This conversation is done.”

And our argument for the night ended. However, my shortcomings would continue to be a topic she picked on often.

Flash forward four months, and it’s January. Only five months and she’ll be out of school, and we can make love, of course, with protection. While we were in love, she had a big crush on a buddy of mine. I’m talking about a super handsome, six-foot-four-inch black guy, a 28-year-old chick magnet, packing an enormous lady pleaser in his britches.

Cyndi and I were at this party, and a friend of hers, Patty, hooked up with Tavon, and they fucked in one bedroom in the house. Patty turned out to be a screamer, and everyone heard how much she enjoyed Tavon. After two hours of lovemaking, fucking, rutting, whatever, she staggered back to the party, visibly shaken, not stirred.

Afterward, Patty prattled to her, day after day, about how great it was. How physically dominating he was, and how wonderful he made her feel.

At that point, my beloved Cyndi developed an obsession with Tavon. She watched interracial porn on my computer at my digs. Constantly she spoke about Tavon and told me he was a real man and said the coldest and cruelest thing, not meaning to hurt me.

“You know, baby, I want Tavon to be me first. I really, really do.” Cyndi destroyed me.

The waterworks exploded.

“Damn it, Jeffery, it’s only sex. What have I told you about these stupid issues you have?”

“I’m too sensitive.”

“You’re like damn tween girl.”

“But people that love each other...”

“Want the other person to be happy. You want me to enjoy my first time, don’t you?”

“Yes, but I thought...”

“I’ll never enjoy it with you, so let me have this.”

Within a few minutes of the argument starting, it ended with my enigmatic, utter defeat.

“So, we’re agreed on Tavon. You call him, tell him what we want, and set it for your place Saturday night. Remember, baby, I must be home by midnight, so say six o’clock, okay?”

“But you promised not to have sex until after graduation.” Gentilly reminded her.

“No, I didn’t. Our exact words were we wouldn’t make love until after my graduation. I didn’t promise shit about anyone else. Are you trying to make me mad?”

“No,” I said, my last protest as futile as the rest fell on deaf ears. “I guess I’ll head to the movies once Tavon’s there.”

“Well, you assume wrong. You’re going to stay and watch. After all, I wouldn’t feel safe without you there.”

Cyndi plopped beside me on the couch and seductively ran her fingers across my chest. Slowly, she moved down my chest, over my belt, to my crotch. The love of my life squeezed me, coaxing my little-finger-dick to stiffen. She buried her fingers in my hair, played with it like a harpist plucking just the strings to tug at my desires, and whispered into my ear.

“I realize you want to watch,” she said. “You want to see that big fat black meat cocksicle open me up and have a front-row seat to Tavon making a woman out of me, don’t you?”

As she stroked me through my khakis, my ding-dong jerked and twitched, turning it into a hungry beast trying to escape its prison. Slowly she rubbed me, saying nasty things. My movements were slight initially, but they built on each other until I squirmed like a worm impaled on a fisherman’s hook.

“Yeah, you want his huge, niggar fuckpole busting inside me as much as I do, right, Jeffie? Want to see him defile your pretty virginal girlfriend, turn her into a white whore for a black man, right?”

The spell she wove sucked me in like her mouth hoovering my prick. Soon, all too soon, I flooded my pants with seed. And, of course, she chuckled on cue, a bitter, taunting giggle. She taunted and teased me about being less of a man. Carving me up, tempting me, and thrilling me simultaneously.

“Baby, you need to understand. I’m the boss.”

“I get it,” I said.

“Tell me, say it, go on, say it.”

“You’re the boss, sweetheart.”

“Make the call.”

“Yes, ma’am.”

Tavon was my oldest friend, and my girlfriends fucking him was nothing new. This wasn’t his fault, not something he set out to do. It was unfair to blame Travon. This was something that had happened. Of all the fellows she knew, it had to be my best friend, Tavon. Events conspired against me. Having an older friend who protected me as a kid, growing up to be such a hunk, was a viciousness of fate.

While Cyndi would be my fourth girlfriend to fuck Tavon, it would be the first girl I loved to do so. In fact, she was my first and only love. Also, Cyndi would be the first girl who fucked him before me. The first virgin I dated wouldn’t be deflowered by me but by him.

My relationship with Tavon had been a constant friendship for many years, yet here we were again. Growing up around Tavon and knowing him as an adult, I realized how attractive he was. How women viewed him as a sexually appealing man and that yet another of my women found him so very appealing only added salt to my wounds.

Who might have predicted he would become such an attractive figure and a thorn in my side? The irony of my situation, while not lost on me, gave me no comfort.

This damned unpleasant development upset me. Still, I had no choice with our relationship set in stone. After all, Cyndi was the boss. There was yet another first in this dreadful situation. This was the first time I’d have to watch my best friend fuck my girl.

With one swift, violent stroke, Cyndi essentially castrated me, emasculated me, and I understood my place. My presence at her meeting with Tavon had nothing to do with her protection. Seeing another man deflower my woman was to humiliate and degrade me. Cyndi’s ruthlessness was not casual, innocent, or unintentional.

Cyndi was a malicious mistress, a ruthless taskmaster, and I was hers, not the other way around. If I were to be with her, marry her, as planned, life would be on her terms. I desperately needed her, and Cyndi used my necessity as her control.

Tavon was more than receptive to the idea. Admitting he’d wanted to fuck her since he first laid eyes on her. When he discovered she was a virgin, he laughed and said, “NICE.”

“No,” I said, “it’s not nice.”

“Well, why the fuck are you calling me?”

“She wants you to take her virginity.”

“Yeah, I’d love that, but why? What’s wrong with you?”

“I can’t.”

“Why the fuck not?”

“She wants you, and I love her.”

“You love her? She’s not your wife yet, man.”

“I know that,” I said.

“She’s a virgin, so be gentile.”

I’d forgotten about his fetish for taking a girl’s virginity.

“No, I’m never gentile.”

“You need to be gentile,” I said.

“Shut the fuck up,” Cyndi barked. “He can fuck me how he wants.”

Tavon chucked, “You her pussy, bro. But she gonna be my bitch, at least this Saturday.”

“I don’t want her hurt,” I said, realizing how brutal he could be.

“Not your choice,” the two said simultaneously.

Saturday at six o’clock arrived far too fast. She made me take her to a sex shop, where she bought the sexiest black lace teddy, matching stockings, and black spiked heels. She dressed in private and wore a long robe to cover her. It was apparent Tavon would be the first to see her in the outfit.

She purchased a black leather choker collar. The thing looked like a plain-jane dog collar, complete with a ring, to attach the tag or the accompanying leash. All afternoon, she pranced about my apartment, cleaning, teasing me, and not letting me touch her as she prepared the pad for the night. Candles were everywhere, small ones, long ones in candelabras, in the living room, dining room, the bedroom.

At a quarter of six, she lit every candle and sat in an armchair, waiting for him to arrive.

At the stroke of six, without knocking, Tavon entered the room. He dressed like a thug, a white sleeveless t-shirt stretched tight, barely containing his massive chest. Loose jeans with no belt hung so low, only his enormous meat-stick held up his trousers. He wore no underwear. His shoes were Air Jordans without socks.

A fine mist on his body glistened in the candlelight. His dark skin would make him almost invisible if not for the candles burning in the room. His handsome face held a demanding glower as he gazed at Cyndi.

He slammed the door shut with force, shaking the walls, held his right hand into the air, and snapped his fingers, calling her to him. His motion was sharp, demanding as though she must jump at the snap of his fingers. A dull thud resonated when the door hit the jam, like the first dirt thrown on my casket. This was when I realized Cyndi would be the death of me.

Cyndi stood, slipping free of the robe. It fell to her feet, revealing her hot, sexy body for him.

A sharp pain pricked my heart.

She strutted toward him, hips swaying, as one foot swung in front of the other, a model showing off on a catwalk. With seductiveness, she moved to him, holding up a small metal tag in one hand and the leash handle in the other. Offering herself to him.

Taking the tag, he chuckled, “Bitch, yeah, that’s your name.” he looked at the back, “Property of Tavon.” Smiling, he clipped the tag in place. Taking the leash, he tugged it, pointing to the floor.

She dropped to her knees.

He seized her hair and jerked her toward him until Tavon pressed her lovely face against his privates. The closeness of his manhood pressed against her mouth made her blush.

“We should put this off,” he said, with a hard edge to his words.

“If I have to wait, I will, sir. I’m sure you make everyone wait. How long do I have to wait?”

“Ain’t no telling,” Tavon said. “I don’t know, you ain’t even made me hard. Ya want to give that a try, bitch?”

“Of course, I do, so want to make you hard,” she said.

With intimidating, demanding tugs, he dragged her to her feet. Another jerk pulled her body to him. She ran her fingers under his T and rolled the fabric over his belly. She kissed his tummy. Working her way up to his pecks, she suckled on one nipple, then the other.

He tossed off the shirt.

“That better. Thought you were some Barbie doll, someone cut the tits off of. Brother, don’t she look like a flat-chested Barbie to you? Tell you straight-out, Bitch, it’ll take more than sucking my titty to get me hard.”

He pushed her to her knees again.

“Tell me, little Jeffie, y’all comfortable with this shit? Cause if you ain’t tough shit. Bro, I’ve always loved fucking your bitches, and this a virgin you marrying and having to watch me fuck her, me busting her cherry, is really nice.”

The statement had a betrayal to it, but I understood he was being honest.

“Don’t stress out. Cyndi doesn’t mean shit by this. It’s just about your little weenie. Come on baby, has Jeffery got a tiny prick?” he said.

Looking up at him, pawing his jeans-clad crotch, she lifted a pinky finger.

“Thought so. Cyndi, take it out and get hard, or we done.”

Unbuttoned his slacks, she pulled the zipper down, and Cyndi moved back as his pants fell. His flaccid Johnson hung there, over seven fat inches, curved, a massive snake ready to consume prey. While it was limp, it twitched and bobbed.

She ran her hand over it reverentially, and the meat swelled, stretching a few inches and plumping some. With her other hand, she cupped one tennis-ball-sized nut, then the other.

His Donkey-Kong continued to grow, and the head peaked out of the foreskin. Cyndi kissed it. His one-eyed snake stretched and swelled, and the python was free. The whole thing stuck out straight as a board and appeared angry, needing something to calm it.