John Vukovic couldn’t believe his luck. Here he was, about to plunge his turgid cock between the wide-spread legs and into the cunt of the girl before him on the bed. A girl like no other he had ever had. Flashing through his mind were the events that led up to this moment.
She was the United Package Express driver who regularly delivered various parcels to his front door. He sometimes had to sign for some of them, so he had gotten to know her a bit. It turned out that they both went for coffee at the same shop in the morning as well. At first, it was just a wave, then, it was friendly chit-chat.
Her name was Tracy. She was tall, slim, and athletic, with long, dark brown hair. She tended to wear tight tops that showed off her small but firm tits. She wasn’t what you would call gorgeous, but she was nice-looking nonetheless. She had a low, sexy voice and wasn’t afraid to talk a bit dirty. She was different in a way that John couldn’t put a finger on, but he still was sexually attracted to her.
The incident that started it all happened one morning. John was engaged in one of his favorite pastimes—that is sexting with another guy on a porn site. They swapped cock pics and some pics of their wives and talked about how they would fuck the other person or couple in a bi-three or four-way. John’s cock was rock hard as he sprawled naked on the bed stroking his dick.
Just before he was about to cum, there was a ring at the doorbell. Knowing he had a package coming that he needed to sign for, he quickly grabbed some shorts and a muscle shirt. Slipping on his shorts as he made his way to the door, John realized that they were quite tight and showed his massive hard-on quite plainly. With no time to change into anything else, he just had to make the best of the situation.
Sure enough, it was Tracy at the door, holding the package and the signature device. John apologized for the delay, saying he was busy as he signed for the delivery. As he did so, he was aware that Tracy’s eyes had lowered and taken in his cock bulge. The look in her eye was different when she looked up. It was unmistakably a knowing look. Her parting comment confirmed her awareness of his stiff dick.
“Thanks!” then Tracy added with a slight smirk, “I hope you have fun. I won’t keep you.”
Embarrassed, John stammered something about, “I hope I see you at the coffee shop,” and shut the door.
Sure enough, two days later, Tracy was at the coffee shop. It was her day off and she was wearing jeans and a tight, white top that clung skin-tight to her torso. No bra. It looked like the top of a one-piece exercise outfit. Whatever the case, he could see the prints of her nipples. And sure enough, she waved him over to her table.
“Hi, John! Glad to see you! I hope you have a minute to talk,” she began.
“Yeah, sure. I’ve got some time,” he replied, slightly embarrassed.
Her friendly smile disarmed him and made him more comfortable, nevertheless, John felt obligated to apologize to her.
“Sorry for the other day. I was…well…busy and couldn’t find any decent pants,” he told her.
“Oh, that’s okay with me. We see all sorts of stuff on this job. I thought maybe I’d interrupted you and your wife or something, but I didn’t see her car there,” Tracy explained.
“No, she wasn’t home. It was just one of those wake-up-in-the-morning guy things,” John said, telling a half-truth.
Tracy put her hand on top of John’s and looked him in the eye, saying, “I get it. I saw the size of your package, and if I hadn’t been at work, I would have joined you.”
John was momentarily stunned. He hadn’t expected this! Finally, he recovered enough to answer her.
“That would have been fine with me. Do you date much?” he asked the brunette.
“Not really. But I like the variety of several men. I probably should let you know that I do have a thing for older men,” Tracy admitted.
“Oh really? I like that!” admitted the fifty-year-old John, enamored with the thoughts of this athletic small-titted girl sharing his bed.
My wife is gone tonight. Would you like to come over?” John asked hopefully.
He figured he had read the signs right and now was the time to be bold. But Tracy got a funny look on her face. She didn’t answer immediately. Rather, she fidgeted with her napkin.
Finally, Tracy answered with guarded eyes, “There is something you should know about me, John. I’m not your regular sort of girl.”
John, missing the gist of the reply, blithely answered back, “Oh that’s okay. I like every sort of girl.”
With a very serious expression on her face, Tracy answered back, removing all doubt, “I mean, I’m not exactly all girl. I have a cock.”
John, staring at her tits, was stunned but recovered enough to reply, “Uh..well…actually, that is okay with me. I don’t mind.”
Now it was Tracy’s turn to be surprised, “You don’t? Really? I mean I feel like a girl, and I’ve got the boobs, but I haven’t done anything to my cock. It’s still, uh…natural.”
“Listen, Tracy, the truth is, I’m Bi. So cock doesn’t bother me. But I would like to see those tits of yours in a…uh…private way,” John admitted.
“Seven at your house? I’ll be there!” Tracy said with a smile.
John had enjoyed sex with other men, but never one with nice tits that looked like a girl. Hell, for most purposes, she was a girl, right? And for that matter, did it matter? The thought made him very hard.
True to her word, Tracy showed up at his house at seven. She was wearing a short skirt that went above the knees and a form-fitting top that showed off her bra-less cleavage and some jiggle. With her makeup done, and the natural androgynous features of her face, a guy would have a hard time guessing she had a dick.
John had to admit this was a whole new world for him. Although he had looked at pictures of sexy “chicks with dicks”, he had never had any close contact with a trans woman. He realized that he did have some old-fashioned ideas on whether “she” was a girl or boy, but realized that “she” would be the best. After all, except for her penis instead of a vagina, she seemed to be a woman. And, of course, Tracy, herself, identified as such. Not that he was particularly prejudiced before, but meeting someone as sexy and interesting as Tracy went a long way to full acceptance.
His only conundrum was how to get the party started. With a guy, they would likely watch porn until they got hard and decided to stop stroking their own cock and stroke each other, starting the fun. With a girl, it was usually a more subtle and lengthy process to get her into bed. Despite considering himself bisexual, John didn’t particularly like to kiss another man. It was a hang-up he couldn’t get over. The fortunate thing with Tracy was that looking at her didn’t trigger that hang-up. She might have a penis, but she was a woman to look at.
John invited her in and they sat together on the couch, making small talk. John offered Tracy a drink and she accepted. Gradually, they both began to loosen up.
“I’ve got to come clean and admit that I thought you were good-looking long before I saw your cock bulge. That’s why I flirted with you. So tell me the truth, was it just morning wood, or had you been jerking off when I rang the doorbell?” Tracy asked with a grin.
“Okay, I admit it. I was on a porn site reading the stories and looking at pics. And I was sexting with a guy on there, swapping pics. So yeah, I was jerking off,” John told her.
“Looks like we have that in common. I like looking at porn and masturbating too. Guys and girls both. I’m kind of more attracted to guys, but enjoy girls too. Weird, huh?” she admitted.
“Not really, I get it. And I admit that I’m very attracted to you,” John said as he put his arm around her.
Tracy looked him in the eye and said, “Show me.”
Moments later, their lips touched in a kiss. A minute after that, the kiss became passionate. And shortly after that, their tongues were in each other’s mouths. As Tracy reclined on the sofa, John began to feel her tit. Her bare leg also excited him. He ran his hand slowly up her thigh to her crotch, judging her reaction. And he got one. She was hard.
“Let’s take this party to bed, If you don’t mind?” Tracy cooed in a deep, throaty voice.
“Oh fuck yeah!” John responded as his hand rubbed up against her panty-clad package.
John led the way and pulled down the bedspread, gesturing to Tracy to get on the bed. There was no doubt that Tracy didn’t mind getting down to business. She was his kind of sex partner. But first, she pulled off his shirt and undid his pants as she sat down on the edge of the bed.
“Nice chest! I like my guys to have some chest hair. I know… I’m weird. Now let’s see your delicious cock,” Tracy said, smiling and running her hands over his chest and pecs.
Stripping his pants and shorts off until they were around his ankles, As Tracy got down to it. John’s nice-sized prick sprung out, erect and proud.
“Ooh, honey! That’s a nice-sized one! I don’t want to spoil the surprise, but it’s a lot like mine,” Tracy informed him.
“Take off that top. I want to see your tits, Tracy,” John commanded her.
“Whatever you want. As long as I can suck your cock, I’ll do whatever you want,” Tracy repeated in her sexy voice.
Slowly, tantalizingly, Tracy took off her top, exposing her small, firm, naked breasts. They were exquisitely topped off with dark nipples. They were perfect tits that looked oh so delicious! John’s member became even harder.
Tracy cupped her boobs and asked, “Do you like it?”
“Oh hell, yes! I’d suck on those all night long!” John truthfully replied.
“Good. I like my little titties. Sometimes I think they are my best feature. They make me so pretty. But now, I’m going to suck your delicious cock,” Tracy replied.
Leaning over, Tracy began to lick his balls, then worked her tongue up his shaft. Finally, she was licking his glans. Next, she slowly took his cock deep into her mouth while her hands played with his nuts and lower shaft. Slowly and expertly, she blew his dick, while John placed his hands on her shoulders. It was amazing! Even if only this had happened between them, it was all worth it! Much more of this and he would burst, filling her mouth with cum. But that was not to be.