Transexual Surprise & Delight

When a new bar opened up in town he decided he would go check it out. He wasn't much into bars, never had been, but single, nearing 50, and having wasted too much of his life being the "good" boy. He figured it was way past time he started to experience a little of what life had to offer.

He got to the bar about 9 that evening, and it was hopping. People were packed inside, Crowds of gorgeous women were standing outside smoking, chatting with the men that were there.

The music was thumping and gave him a mild headache, but he pushed through ignoring it. The dance floor was a mass of writhing bodies. In short it was way outside of his normal experience. However, the dark lighting and loud music pretty much made anyone alone invisible.

He made his way to a small table in a very dark corner, and before he could even sit down a harried waitress appeared and asked for his drink order. Not being a drinker he just ordered a soda. She nodded and before she could run off to get it, she looked up and asked, "And for the lady?"


He blinked, but then turned and saw a tall, elegant black woman standing just behind him. She placed her hand on his shoulder and leaned forward and whispered huskily in his ear, "I'll have a rum and coke."

"Rum and coke," he said automatically to the waitress, who then hurried off.. The woman then guided him into the booth and slid in next to him, "My name's Monique, honey, how bout you?" She looked to be in her mid-30's, taller than he was, but She was beautiful, Her skin a dark chocolate, slender, with large, round breasts contained in the tight red dress she wore. Her legs were long and perfectly formed, he could only imagine how beautiful her ass was not having gotten to check it out.

By contrast, he was older, nearing 50 with graying hair, a slight paunch in the middle that he just couldn't seem to make go away. He wasn't in horrible shape, but not the greatest either. Though a niece of his told him once he had a "dad" bod, whatever that meant.

"John, nice to meet you Monique," He replied.

She leaned in and gave him a kiss on the cheek an whispered once again in his ear, in that same erotically husky tone she had used earlier, "very nice to meet you, John." The way she said his name, a very common, not at all sexy name, sent thrills through him.

The waitress then appeared and sat their drinks down, and he paid her, tipping her generously, then they were alone. Sipping their drinks, listening to the music, talking about different things, hobbies, work, home life, kids, neither one had any. Monique's hand would sometimes stray to his and her fingers would lightly graze the back of his hand and sometimes up his arm, which sent shivers of excitement up his spine.

After a couple more drinks, She leaned over, and this time, before she whispered in his ear, her tongue wetly flicked out and flicked his ear lobe, something that always drove him wild, "How about, you and I get out of here and go back to my place?"

He was shocked, and honestly didn't answer right away, not sure he even heard her correctly, but then he turned and looked into her eyes and nodded.

She stood up and took his hand pulling him up out of the booth. She was strong, stronger than him and taller than him. She was just pushing all his buttons this night.

As they made their way out of the bar, he saw her pull a pack of cigarettes out of her purse, and he couldn't believe his luck. He had always had a thing for women smoking, and if she lit up, he was certain he would do anything she wanted.

She stopped for a second as they got out the doors, and did indeed light up a cigarette, which he watched with wide, hungry eyes, and as she exhaled she smiled at him, and offered him a cigarette. He didn't accept, politely declining and she then asked if he minded her smoking to which he quickly and eagerly said not at all.

She smiled again, a dazzling smile showing her two rows of perfect white teeth, took his arm in hers and they walked to his car.

A short time later, they were in her home. A modest little 2 bedroom house and he was on the couch while she fixed drinks. He told her just tea or soda would be fine and she had nodded. Then smiled as she brought the drinks over, another freshly lit cigarette dangling from her lips.

Sitting down next to him, she handed him his drink, took a drag and exhaled towards his face. Not directly at him, but just in his direction, almost as if she were testing to see if what she suspected were true. The sharp intake of excited breath told her everything she needed and she raised her glass and smiled saying, "To new friends!"

He toasted and drank deeply, suddenly very thirsty. She sipped and watched him, watched as his eyes widen. Reaching up and holding the bottom of the glass she whispered, "Drink it all up, baby."

He did, swallowing every drop of the liquid. She had mixed in a little alcohol, but it was the other item she added that she needed to work. Things would go much better if he were relaxed. Not that she was worried, he wanted her, and she suspected he wouldn't much care about the surprise she had for him, but better to be sure.

As he visibly relaxed and looked at her, feeling light-headed he asked fuzzily, "that wasn't soda was it?"

She smiled and shook her head and kissed him softly on the lips, exhaling small clouds of smoke around his lips as she did so, "Just something for you to relax, baby, and help get us in the mood for the fun I am sure we are both wanting."

He nodded, he had wanted to try new things, and Monique was certainly helping out with that. His mind wasn't impaired at all and as he gazed into her dark eyes, he looked at her and said, "I want to experience everything."

She smiled brightly and kissed him harder then. Her soft lips pressing against his hard. The contrast of his pale skin, to her dark skin was mesmerizing whenever he noticed it, and he savored the taste of her smoky lips the feel of her breasts against his chest. The feel of the....

What was that? His mind raced as he felt her straddle him, felt her press up against his belly. Felt the hard, thick lengthy bulge in her dress? His mind thought maybe the drug was playing tricks on him. Maybe She was a Dominant woman into strap on play? Not odd that is where his mind went first, he was more submissive to women than anything else.

As her tongue explored his mouth thoroughly, she felt him yielding to her kiss, yielding to her completely. She did feel his surprise when she pushed her pelvis up against him and knew he had felt her excitement. She was not going to hide what she was with this man, but the reveal was delicate, and she whispered against his lips, "Do you like it?"

He looked into her eyes and slowly nodding his head, whispering breathlessly, "Um..yes...Mistress?"

How cute, she was a top yes, but no one had ever called her dominant before and she giggled, "You don't have to call me Mistress silly boy." Then it dawned on her what he thought and she leaned in placing a finger against his lips she pushed it into his mouth. He did begin sucking it as he looked into her eyes she whispered, which some trepidation, this was always the hardest part, "I'm transexual."

He blinked, but he didn't stop sucking her finger and she begin to work it in and out of his mouth, feeling his tongue flicking over the underside of her digit. Her eyes searching his for some approval, acknowledgement, hatred derision for her luring him here and giving him some drug.

She saw none of that in his eyes. When she pulled her finger from his lips he looked up at her, and in a soft, very submissive voice she thought whispered, "I've never done that before, but...do you...do you want me to ....."

She placed her finger over his lips and said, "I am a top. So yes, I want you to do everything for me. I will take care of you though as well."

He nodded and whispered nervously, "I'm..willing to try, but...but I am very...tight...in the past...I've messed around some with plugs, but never big ones, and that was a long time ago."

She nodded understanding and eased his mind, "I am very patient, baby, don't worry, I will be quite gentle, until you say you don't want me to be." She said the last with a coy smile, maybe she could be a bit dominant after all, at least with this sweet man.

He smiled back at her and then said, "You lead, I'll follow.....Mistress." The way he paused and said that, she realized it was his way of surrendering to her, and offering his full consent.

She stood then and helped him, grabbing her cigarettes and leading him into her bedroom. She helped him undress and sat him on the edge of her queen-sized bed. Reaching back behind her, she unzipped her dress and wiggled out of it.

His eyes marveled as her dress stopped at her hips. He focused on her large round breasts. She was quite proud of them. The hormones had done their part, and only one enhancement was needed and she had large sensitive dark brown nipples, topping the beautiful mounds that he stared at hungrily.

She pulled his head to them, and he kissed and licked at her flesh eagerly. Flicking his tongue over her nipples, then suckling them gently in. She took a deep breath and shivered with lust as she held his head to her. Her other hand pushing the dress down until it dropped to the floor. That's she she felt his hand. His slowly, tentatively touched her cock. His fingers exploring the length and girth. She was thick and quite long. 8-9 inches, but she hadn't measured in some time. She had been very well endowed before transitioning, and had lost maybe 2 inches off her original size. She felt his fingers fondle her balls, and all around her pubic region. She was shaved smooth, and he seemed to like that.

Then his hand wrapped around her shaft. He had large hands, which was one of the first things she had noticed about him. As he gripped the based of her shaft, gently, but firmly, she sighed in pleasurable anticipation of what was to come. He stroked her as he suckled at her breast. The tip of her cock touching his chest as he did so.

Then looking up at her his eyes almost pleading, She nodded and said softly, "Yes Baby, I want you to suck it for me."

He didn't respond just kissed down her belly, then his lips and tongue touched the sensitive head of her cut cock. She leaned her head back and breathed deeply as he licked all around the head, seemingly a bit nervous about taking it inside just yet, but she was content to let him explore.

And that he did. He thoroughly explored every inch of her cock, he explored her balls thoroughly. She had had great blowjobs from men before, but this was different, this was someone totally inexperienced at this, trying something new for the first time, and wanting to thoroughly explore it all.

Soon though, lust and need outweighed exploring and she reached down cupping his head gently but firmly and guiding him, until the head of her cock was poised at his lips, "Open wide, baby," she softly commanded him.

He obeyed and soon her thick, veiny shaft was sliding across his tongue, and poking at the back of his throat. She eased up a bit when he choked and started to gag a little, and stroked his head whispering, "relax, baby, take your time, adjust....you'll get the hang of it. She let him just suckle on a couple inches, getting used to it. She knew it would take some time before he was able to truly deep throat her, but with this man, she wanted to make the time, and teach him just how to do it right. She wanted to truly fuck his throat one day, and she would patiently help him adjust until she could do just that.

So she let him go at her own pace, then slowly pulled his head off her cock, almost reluctantly, then leaned down and kissed him deeply, one hand pulling a large pillow to the center of the bed.

She then guided him to lay over the pillow, adjusting him until his sweet, cute ass was pleasantly raised. She spread his legs slightly then grabbed her lube. She rubbed his bottom softly, firmly, squeezing his cheeks. He had a nice round bottom, and she leaned down and kissed it softly.

"I want you to fully relax baby," she said softly again as she poured lube into his pale ass crack, and begin to massage it in, circling his tight little hole. "Just relax, Monique's gonna take good care of her sweet boy." He sighed and moaned and she thought actually wiggled his bottom a bit for her.

Slowly, very slowly, she eased her finger into him. Oh, was he ever tight, she felt him grip her finger, and tense up, and she used her other hand to rub his back soothingly, murmuring softly, "relax, baby, relax, it's OK." For several long moments, she just held her finger there, just into the first joint, and let him adjust.

She felt him relax some then, and ease a bit more in, slowly adding a bit more lube, and working that finger in and out. Once she was able to move it fluidly in and out of his sweet tight hole, she slowly introduced a second finger and started the process over.

She continued until she was comfortably working three fingers in and out of his ass, and instead of clenching, tensing and groaning, he was moaning in pain and actually writhing a bit.

How she loved it when a good bottom writhed, so sexy. He was a natural, even for this being his first time, and she almost wanted to plunge into him right then and there, but patience was the key. If she hurt him now, she would scare him off and she would lose this sweet, cute little man. That was something she didn't want to do. She genuinely liked him, and felt that he was just the man she had been looking for, a man to accept her for who she was, and perhaps even fall in love with her.

She imagined them getting married. His family may have an issue with accepting her, but that was something they would cross. Her family certainly wasn't all that accepting, and if they found her with a white man, they'd shun her completely. But she was past caring about all that silliness. It was just as wrong of her family to not accept him for his whiteness as it was of them not accept her for her transition. As for his family, she would deal with that when it came up.

For now, she just eased her fingers in and out, twisting them slightly with each new penetration until he was fully writhing and moaning, and her other hand finally reached under and grasped his cock, stroking it. She should have been doing that all along she realized, but so lost in the joy of his sweet little ass she had forgotten that, and she heard him moan with lustful intensity when her soft hand closed firmly around his hard shaft.

He wasn't as long as her, but she could tell he would be a very pleasant mouthful for those times she would orally please her man. Then she shook her head and thought, not her man, her boy, yes, she thought he would prefer that. She didn't want him to cum yet though, she soon she stopped stroking him and worked her fingers out of his ass leaning down, kissing his ears, whispered hotly, "are you ready, baby? Are you ready for me?"

He nodded his head almost eagerly, and then said what she wanted to hear, "Yes...yes, please fuck me..."

She rose up and straddled his legs. Squatting down, she spread his cheeks and got the head of her cock position against his slick hole. She added more lube and rubbed it into her shaft and a bit more to his hole, then pushed. She met some resistance, but she had done her job well loosening him up and soon the thick head was sucked in by his anal ring and she heard him gasp. Yes, this was different than her fingers, but she let him adjust and soon he relaxed again and she pushed in deeper.

Inch by inch, taking her time as she savored the sweet tightness of his virgin hole, marveling at how hot it was. It had been a long time since she had been a virgin, and a long time since she had been with a virgin. Tonight had turned out far better than she had hoped when she got ready to go to the club. She wasn't sure he knew that it was an LGBTQ club, but it seemed he probably wouldn't have cared either way.

Then she felt it, felt herself bottom out inside him, felt his hole grip around her shaft tightly, and she leaned down over him, pressing her breasts against his back as one arm wrapped around his throat, not choking him, but holding him, her lips kissed his ear, her lust making her breath hotter as she whispered, "Hang on, baby, we're going for a ride."

He moaned, and she felt him actually press back with his ass as he whispered back to her, "I'm yours, Monique, please...take me."

That was all she needed, she begin to thrust into him, her hips rising and falling as she stayed laying down on top of him. No need to be rushed or urgent for this first time. There would be time enough later for the hard pounding fucks she truly loved to give. This was about easing him into it, making him want more, need more, and that seemed to be working.

Soon she was rocking against his body, in and out, plundering his sweet bottom. Both their lust-filled moans filled the darkened room, lit only by the soft, subdued lighting of her bedside lamp. Her hips mashing against his round ass each time she bottomed out in him.

Her hands exploring his hair shoulders neck and face, until she could hold back no longer and raising up slightly, her hands on his shoulder, she did begin to thrust harder, deeper. Gripping his shoulders more forcefully now, she was bouncing on his ass, thrusting deep. The sound of their bodies slapping together was insanely hot to hear ears. His white body beneath her black one was beautiful in the simple blending of colors. She thrust harder and faster. Her breathing more ragged now as she neared her climax.

It happened suddenly. She slammed into him, and tensed up, she heard him moan loud as her cock expanded inside him, stretching him even more, then she saw starts, explosions rocked her body as her cock erupted inside him. She ground her thick shaft deep inside his clenching hole, flooding him with her seed, breeding him. She savored every tingling pulse through her shaft into him, until soon she was spent and lay down on his back breathing deep and kissing his ear.

"That was amazing, baby," she eventually breathed into his ear. He nodded and wiggled under her. She rose up, letting her cock slip out of him with a pop, followed by a very sexy to her eyes glob of her cum bubbling around the opening. She helped him roll over and discovered why he had wiggled. The silk pillow case had a large, wet dark spot right where his cock had been, and she realized he had cum while she fucked him. Cum quite a bit. She rubbed her finger in it and tasted him. Closing her eyes and savoring his taste.

She then lit a cigarette, toss the pillow aside and lay down next to him, cuddling him to her and giving him a deep smoky kiss and whispered, "I hope we can do this again sometime."

"His eyes were half closed and she realized his was drifting off, but he whispered sleepily, "I hope you never stop doing this to me..."

She hugged him tight and held him close the rest of that night. The next morning saw a repeat performance, and this time she sucked him off and swallowed his load.

They took a shower together, and had breakfast. Then holding hands went out on her deck and sat in the morning sun, side by side, his head leaning on her shoulder as she smoked a cigarette. Soon, he was in front of her sucking her cock, and now eagerly trying to take every inch into him.

She laughed and said, "easy boy, you'll get there, take your time..."

She trailed off and sometime later, she let taste her cum straight from the source.

The spent that entire weekend together. And the next weekend. Soon, she sold her house and moved in with him. Yes, the trouble she anticipated with her family arose and she just ignored it. His family was cautious, but they seemed to accept her, even if they didn't understand her or him for choosing her.