Transexual Initiation

At 50, he was alone. He had had relationships in the past, but none had never lasted more than a few years. The longest had been five. He had pretty much given up and resigned himself to spending the rest of his life alone as a bachelor.

He had a home from his last marriage that his ex wanted no part of when she left. He had his dog, a cat, three bedrooms, a belly that no matter how hard he tried he just couldn't seem to make smaller. He wasn't huge or anything like that, just a pleasant pot belly. He wasn't insanely tall, slightly above the average for a male, though at his age, he noticed that instead of standing taller, he was actually a bit shorter.

There were other things that due to some minor health issues, didn't work quite the way they had used to. He hadn't truly taken care of himself all those years of misspent youth. Misspent in that he only discovered many things later in life that had he known when he was younger, may have changed the course he took entirely.

One of those things was fetish. Oh, how the internet had opened his eyes to the fetish world. Sure, there were some things that he just couldn't fathom, but others, others would send him madly into the masturbatory world that he had lived in since his early teen years. Smoking, golden showers, domination, submission, bondage, so many things to explore. The problem was he explored them all from the safety of his own home, alone, and unfulfilled. Life, he decided was dull.

Oh, not to say that he didn't splurge for the occasional "working girl." They were generally kind, and some didn't even try to rush him to orgasm and out the door. Some took their time with him. Some seemed to genuinely like talking to him. They enjoyed his little request that they just lay naked next to him and smoke for him, while teasing his nipples, or sucking on his neck. He never asked for sex from them. Though that did happen once or twice, and was quite magical. He just always seemed to find his own hand better than anything else. Really, it was about the companionship.

He couldn't afford to do that often, though, and for the most part, he just lived a lonely life reading erotic stories online and viewing the "hub" searching out those videos where he could imagine a fantasy scene and talk himself through a mind blowing orgasm.

This all changed on one magical day. He was surfing one of his many fetish sites he enjoyed when an instant message popped up. Curious he opened it to see a picture of an insanely gorgeous woman with long, dark, brown hair, a curvy figure, with full round breasts. She was wearing panties and he could only imagine how her pussy must look. She looked very tall in the picture and indeed in her profile it announced her height at 6'3". Her stats went on to say she was a heavy smoker, and had a fetish for men who loved her smoking. She didn't discuss her weight, as she put it, "a lady doesn't discuss such things." He liked that about her. Her profile stated she was in her early 30's.

The message he received simply read:

"Hi, how are you? My name is Annette, and I just read your profile and think that you and I could be quite compatible. It says you are in (insert state of choice here), and I am, too! I think we may be close enough to actually meet! Would you like to get coffee sometime?"

He took a moment to respond, as the picture he had posted only showed his face, and he was always quite nervous about sending a full picture to anyone, as he had been laughed at in the past. A shame how some people can treat others, when a simple, "I'm not interested" would suffice.

So, he wrote back and said simply, "Yes, I am there, and I would love to have coffee sometime." He hated coffee, but he could drink something else and would happily buy this lovely woman coffee.

She sent back a smiley face emoji and then they discussed a day and time when they could both be free. He checked and re-checked her profile and re-read their discussions many times over the next few days in preparation for the first date he had truly had in over 5 years. They chatted a few times prior to the meeting time as well. Mainly, just to say how excited they were that they were actually close enough to meet.

The day finally arrived, and he took care in his grooming. Something he usually didn't care too much about. Working from home had made him quite lazy in that regard. But for this, he dressed casually, but not too casual. He had got a hair cut, shaved carefully and brushed his teeth twice.

He arrived at the small coffee shop about 5 minutes early, and saw her sitting already at a table over by the window in a corner where they would have some privacy. He smiled and waved, and she stood. As he neared the table, he realized that she was every bit of the 6'3" she had described in her profile, and they shook hands. She had large hands. He thought that was odd, but then dismissed it, and they sat down. A waitress took his order and refilled Annette's coffee, and then they just sat and stared at each other.

Annette broke the silence first, "So, did you wake up with butterflies in your stomach this morning? I sure did." She chuckled softly, and he actually loved how deep and sultry her voice was, he figured from the smoking, but didn't care. It was sexy.

"Yes, I did, very much so, I truly haven't felt this way in years." He responded, relieved that she sounded easy to talk to.

She then reached over and laid her hand atop his, and held it there, her eyes looking at him as the waitress brought his order and again topped off her coffee. Once the waitress had left, she frowned, and lowered her eyes a bit, taking a deep breath, she said softly, "I kind of nervous about what I need to tell you next, because I am not sure how you will take it, though, if I am reading you right, and you seem like a kind man, then I think it will be fine, but I can't be sure."

Oh, God, he thought, she was married? She was just wanting money, and this was all a scam...the possibilities went through his mind rapid fire as he just stared back at her, not feeling it appropriate to talk at that moment.

She finally looked up into his eyes and leaned forward, almost conspiratorial, and whispered, "I...I am transexual."

He blinked, and remained silent for a few moments, until he saw her start to withdrawal her hand and look away, so he reached for it, and held her hand. She looked back at him, and he realized just how startling deep and brown her eyes were, the kind of deep, beautiful brown eyes that he always found mesmerizing, "Don't go, please. You took me by surprise is all, and I am not offended, nor put off in anyway. I am curious, yes, since I have never been with a transexual woman before."

She smiled a bit shyly, which seemed out of place on this confident appearing woman who had boldly asked him out to coffee in the very first chat message she sent him. He leaned forward a bit and said to her, "I'm...actually kind of into the idea."

She withdrew a bit then, and said stiffly, "I'm not a fetish."

He blinked, and shook his head rapidly, "I ...I didn't mean it like that, honestly, that is not what I meant at all. Just...oh bother, why can't I ever form words around a beautiful woman...properly,...I..."

She took pity on him then and reach up and caressed his cheek, "It's OK. I don't think you meant it that way at all. Truth be told, it almost seems we ask to be fetishized with everything seen on the site we met on, and in some sense, it doesn't bother me, but I don't want that to be everything between us. I think there could be more."

Looking into her eyes he could see the truth of that, and he nodded and said to her, far more confidently than he felt, "I would like to explore that with you."

"I'm glad, and just so you know, we did meet on a fetish related site, and I am willing to explore all sorts of things, but I just want more than that, I am not a young woman anymore."

He nodded in agreement, and said much the same thing, that while he would enjoy exploring all sorts of things with her, he was not young either and had no time for games, and an intimate connection was preferred.

After this exchange, they talked about different things and eventually parted, with the firm commitment to a real date the next week. How he made it through that week he would never know. He was nervous, he was elated, he was excited. Many emotions flooded through him throughout that entire week, and he at several points almost talking himself out of it.

The last message he received from her asked him if he still wanted to go out, and he texted back impulsively, "YES!" He was determined by the morning of their date that he was not going to have another "what might have been" moment in his life.

He picked her up from her apartment at 8, and they went to dinner. They ate light, and talked and had a great time. After that, they went down to a local park and walked hand in hand til they came to a small private bench, where they sat to relax under the starlight. When she pulled out a long, white cigarette and placed it between her red lips, he quickly lit it for her and she placed her hand on his wrist to steady the flame, and turned her head ever so slightly, and let the exhale waft over him. She truly did understand him.

He sighed and breathed in the aromatic smoke from her lips, and Then she placed an arm around his shoulders and pulled him against her. In the past, in the same situation, he would have been in her position, and she in his, but with their height difference, this was more comfortable, and he found himself liking that she was taking the more dominant role.

She smoked in silence for a bit, always angling her exhales down towards him, and he just lay with his head against her shoulder enjoying the intimacy of the whole situation. Eventually, she turned toward him, and pulled him closer, leaning down, and placing her lips against his. As her lips parted, he felt her tongue taste his lips, and felt the smoke from her last drag caress his face. He breathed it in as she deepened the kiss and let her tongue explore his mouth.

They made out rather passionately for about 20 minutes, before she breathlessly asked, "Would you like to come back to my place?"

He nodded, unable to speak, and they rose together, walking back to his car. When they arrived at her place, she opened the door, and waved him toward a comfortable looking love seat while she went into the kitchen and poured drinks. He wasn't a drinker, and she brought him iced tea, while for herself she had a glass of wine.

They toasted to a fine evening, and spent a few moments just savoring their drinks, and the closeness they both seemed to feel for each other. When she placed a hand on his thigh, and began to caress it. She then asked him softly to reach over and get her a cigarette.

He reached and got it while her hand continued to massage his thigh, squeezing it, rubbing it, moving ever so closely to the bulge in his pants. He placed a cigarette between her lips and lit it for her. She let it dangle as she exhaled the smoke. He watched it as it wafted from her lips over his face. Then she spoke, softly, sultry and asked, "Tell me, have you ever watched transexual porn?"

The question caught him off guard in that intimate moment, and as she looked into his eyes and took a drag he said simply, "Yes, some. Not a lot, though."

"Why not?" She asked this with a coy, teasingly little smile, little puffs of smoke coming out of the corners of her mouth as she spoke.

"Oh, well, most of it involves men with big cocks topping the transexual, and I tend to go the other way in what I watch."

"I see, so you like the "big cock shemale porn?" Her tone was teasing.

"Oh, doesn't have to be huge no, not even particularly big, I ...I just like to see the woman in charge, and taking the top position."

She nodded and leaned forward kissing him, "I was hoping that was how you felt. We could have made it work the other way, as I am versatile, but somehow with you, I feel more...top."

He smiled and made some off-hand remark about how he just had that effect on ladies. She laughed in that sexy little way she had, and then stood up and held out her hand. He took it and she pulled him up and right against her, his face in her cleavage, as she hugged him she whispered, "Let's get more comfortable."

She led him into her bedroom, and lit a few candles, bathing the room in their warm glow, then walked over to him, almost like a cat stalking its prey. He gulped nervously, but stood his ground as she arrived and began to tug his shirt upwards. Within moments he was standing naked before her.

She kissed him again, then placed her hands on his shoulders and gently pressed him to his knees before her. Softly, seductively she then asked, "Would you like to see?" Of course she knew he would, and he nodded his head eagerly.

Slowly she began lifting her skirt, then just before he would be able to see anything she turned around and bent over, instead now pushing her skirt down over her firm round ass. God she knew how to tease.

As the skirt fell to the floor, she raised back up, and then slipped her panties down, holding her thighs together so he could truly see nothing, as she wiggled that gorgeous ass playfully til letting her panties drop. She looked over her shoulder and down at him, smiling then she lit another cigarette and blew the smoke down at him, and whispered, "Are you sure you're ready for this, baby? It may be more than you bargained for? And once I turn around, there is no going back, you are going to be my bottom for the night."

He loved the dominant tone she used to say that, and he whispered back, leaning forward to plant a kiss on one firm ass cheek, "Yes, please, I am so sure, Please, I want to be yours. Then he said it, the fetish line he had always wanted to say in this situation, hoping it was something she approved, "Please...just make me Your bitch?"

When she smiled, turning around she looked down at him, his eyes were drawn to the roughly 7" of smooth hard cock that smacked his cheek wetly, precum already oozing out of the little slit. Her crotch was smooth, and her balls dangled beneath like two plump grapes in their sack.

"Then my bitch you shall be. Open up, bitch." Her tone was demanding, with a hint of playful seduction and as he parted his lips, she pushed the head of her cock in, sliding it until he gagged, and started to pull back. Her hand on his head stopped that.

"No, no, my bitch will never pull back from his Woman's cock, is that understood, bitch?"

He nodded his head as his eyes looked up to the tall, beautiful woman with a cock that was just slightly bigger than his own. The feelings that rushed through him as he felt that smooth hardened flesh fill his mouth were intense. He had never felt more alive in his life.

She then begin to gently thrust in and out of his mouth. Explaining to him gently that since he was new to this, she would have to train him to be a proper cocksucker over time, but for now, she just wanted to get a fell for his mouth. At one point when he had relaxed with her gently thrusting, she pushed a bid harder and deeper, the head penetrating his throat. He convulsed and choked hard, gagging and she pulled back quickly, til just the head was in his mouth.

"Ok, bitch?" He nodded, catching his breath, then composed himself and looked up at her.

"Ye..yes...just...wasn't ready for that."

"I know, but one day, you will be an expert!"

He believed that she would teach him to be just that.

She then grabbed a handful of his hair and pulled him up on the bed, positioning him on all floors facing the headboard. She climbed up behind him, and picked up a tube of lube behind her on the dresser, then began to work it into his butt. He moaned a bit a first, then gave a small cry as she penetrated a bit deep, and she slowed down, rubbing his back gently, her fingers stopping inside him letting him adjust as she blew her smoke over him. He could see in the mirror how hot she was like this, and he wasn't about to stop her.

So she worked his ass over until he felt stretched and a bit numb. Then she announced, "its time baby, are you ready to get fucked for the first time?

He nodded, again, not able to speak, but wanting to shout it to the heavens that this lovely vixen was conquering him. Then he felt it. The tip of her cock pressed against his opening. She added more lube, then pushed. He felt the pressure, felt his hole yield to her. It wasn't hurting as bad as he feared, and he let her continue, until she pulled back.

She then began, fucking him back and forth. Her cock soon was in balls deep and she was thrusting madly. He found himself holding on to the bed with all his might as she plundered his tight, once-virgin hole. His entire body felt more alive to him than it had since that first magical moment he had discovered just what an orgasm was. She simply continued thrusting, laying down on him, he could feel her breasts mash against his back as she ground inside him, and reached around, her arm taking his neck, and pulling his head up toward her, and hissed hotly in his ear, "Your mine bitch..." He could only nod as she continued, "But for this one time, I will let you decide...where I cum...your tight little manpussy? Or you mouth? Decide now, my bitch...or I will decide for you."

His response was simply, "Please...please cum in my mouth...?"

His plea was heard, his wish granted. She pulled slowly out of his clenching hole and using his hair, jerked him around until he was again facing her cock. He opened his mouth and she slid the tip in. Closing his lips around it tightly, she gripped her shaft and stroked it. After several moments of stroking, she then pushed further in, and told him to work his tongue. He did. He was soon rewarded with one of the biggest cum loads he had ever experienced outside of watching porn. It seemed to go on forever with her moaning and just holding her cock inside his mouth. He swallowed as fast and as much as he could. A few drops dripped down his chin, and she smiled and as she lit a cigarette, scooped up the escaping drops and when she pulled her cock out of his mouth, she shoved her fingers in, making him lick up ever drop.

They slept cuddled up that night. They had a third day, a fourth. Eventually after a few months she moved in with him. They now live happily exploring their fetishes together. So many wonderful fetishes to explore, in the privacy of his own 3-bedroom home that he now shares with his Transexual Top Lover, who loves to dominate him in bed.