tagTranssexuals & CrossdressersPleasantly Surprised

Pleasantly Surprised


It was Friday night and Robert was sitting at home alone. His roommates were both out on dates, and his girlfriend, correct that ex-girlfriend, had moved all of her things out three weeks ago. It had been one of the dullest months in his adult life; four weeks of sitting in front of the television, eating pizza drinking beer and watching absolutely nothing had him going stir crazy. He needed to get out and do something.

A man can only sit at home flogging the dolphin for so long, he thought.

"Fuck it," he proclaimed to the empty house. "I'm going out. There's nothing wrong with that right, Mikey?"

The small brown and white dog in his lap cocked its head to the right and looked at him questioningly.

"That's right. I knew you'd agree."

After a quick shower and shave Robert hit the road, not knowing exactly where he was going to go. He bounced around town for a while before finally parking his car downtown and continuing on foot. He wandered aimlessly through the milling sidewalk crowds until he spotted a little blues club that didn't look overly crowded with teenage kids breaking in their fake ID's.

The club smelled of old cigars and old whiskey, lending a very soothing subdued feel to it. The lighting was low, with most of the ambient light being thrown by candles adorning each table. The band was just warming up for their set, so he quickly grabbed a seat and ordered a drink. While patiently awaiting his Captain and Coke, he surveyed the room. There were only thirty or so people populating the tables in the center of the room and the bar along the far wall, mostly couples or groups of friends conversing in hushed tones.

From the front of the club the melody BB King's "Sweet Little Angel" filled the air; the band was starting. For the next twenty minutes his world was filled with the soulful sounds of a blues guitar. The band was surprisingly good, only covering a few songs with the majority of the set filled with original songs; it didn't take long for him to become lost in the music.

As the band broke for a short intermission, he noticed that the place had really filled up during the first set. The bar area was packed, and nearly all of the tables were full. As he scanned the room for a waitress he noticed two women standing near the door, scanning the crowd, presumably for a place to sit.

One was tall, with long slender legs and a nicely toned body adorned with a perfectly round and firm set of C-cups. Her companion was a shorter, curvy brunette; thick legs, bubble butt poured into a pair of tight jeans and a heavy set double D's. Both were absolutely gorgeous in their own right. They were standing close, the brunette's arm draped lightly around her friend's waist. After a moment she locked eyes with Robert and pointed, whispering to her friend before they started to thread their way through the crowd toward his table.

"Do you mind some company?" The blonde asked as they walked up.

He eyed the women up and down, making no effort to hide it.

"Be my guest." He smiled and motioned for the two to join him.

"I'm Vicki," the blonde introduced, extending her hand, "and this is Natasha."

Robert took her hand. "Robert. Nice to meet you."

Natasha just nodded and offered him a quick little smile. She seemed a little nervous.

As the band returned for their second set they sat there, drinking and talking, just having a good time. A little flirting was going on, but Robert was beginning to think the women were a couple.

Great, just my luck, he thought, the one night I actually go out, the only women I meet are lesbians.

He excused himself for a moment and made his way to the restroom, feeling like there was something off with him tonight. He checked his reflection in the mirror and saw nothing amiss: his short blonde hair was lightly gelled in place as always. Below his brow, icy blue eyes, which he thought of as his panty dropper eyes, peered back at him.

Satisfied that he looked fine, he returned to his table. He found that the women had moved seats, leaving an empty chair between them. The forth chair surrounding the little round table was missing.

"Have a seat," Natasha patted the empty chair between them.

Robert sat and the two beauties quickly leaned in close to him. After a moment's consideration he put his arms around each of their shoulders. Both gave him warm, reassuring smiles.

Hmm, maybe this night won't be so bad after all.

Halfway through the band's third and final set, Vicki leaned in close and asked Robert if he'd like to go hang out somewhere a little more private. He quickly agreed, trying not to sound too eager.

It turned out that they shared a place just down the block near the river in an old converted warehouse, so the trio walked over from the bar. As they rode the elevator to the sixth floor Robert gloated about his good fortune.

Wait until Jimmy or Drake hears about his. His eyes scanned the two women he shared an elevator car with.

Vicki was in a short black leather skirt that was tight, showing off her firm high ass and miles of leg. Her strapless white top left the top third of her breasts delightfully exposed. He was pretty sure they had cost her a pretty penny.

Natasha on the other hand was in a pair of dark, hip hugging jeans that seemed to be painted onto her round bottom and thick thighs. Her top was charcoal grey and covered her entire bust; tying around her neck, save for a large diamond positioned right over her cleavage.

He tore his eyes away as the elevator came to a stop and they pushed open the metal guards. The apartment was a loft; the single open space broken only by a bar at the kitchen area, and a raised platform at the far end that seemed to be a bedroom without walls. A bathroom was tucked into the corner as well.

Robert sat on a long, low couch while Vicki fixed them all drinks and Natasha lit some candles and put on some music. They girls finally joined him, taking places on the love seat opposite the couch.

As they sat talking, the conversation gradually shifted to more sexual topics.

Feeling uninhibited by the alcohol, Robert asked, "So, have you two ever, uh, slept together?" Their shared look was all the answer he needed.

"I have an idea," Natasha announced, "let's play truth or dare."

Vicki quickly agreed, looking at Robert for approval.

"Sure." He nodded.

"Great, I'll start," she squealed. "Truth or dare Robert?"


"Have you ever had anal sex?"

"Easy, yes several times with my ex-girlfriend."

"Okay, your turn."

He looked at Natasha. "Truth or dare?"

"Truth...this time."

"Same question then: have you ever had anal sex?"

She leveled her gaze at him and playfully slapped her ass. "This ass is far from a virgin honey. Now my turn: truth or dare?" She was still looking at him intently.

"Truth," he repeated.

"Okay, have you ever had sexual thoughts about another man?"

"Um no." He quickly answered before turning to Vicki. "Truth or dare?"

"Dare," she said firmly.

Robert thought for a moment. "Take off Natasha's top and suck her nipples."

"Come on, I thought dares were supposed to be something you wouldn't normally do," she laughed as she moved next to Natasha. She quickly undid her top, letting her heavy jugs fall free. Her golden eyes locked onto his as she lifted one of the globes to her mouth and slid her tongue across the fat, erect nipple.

"My turn again," she said finally," truth or dare Robert?"



"Truth," he repeated.

"Fine. Have you ever had sex with more than one partner at a time?"

"No. I have with other people in the room, all having sex on their own, but never like a threesome or anything. Now, truth or dare Natasha?"


"Take your pants off and finger your pussy."

"I thought you'd never ask," she sighed. Natasha stood and shimmied her pants down, revealing that she wasn't wearing any panties. She ran her hands down her tummy and over the mound of her pussy with its dark landing strip of pubic hair above her protruding lips. She dropped back down to the couch and spread her legs, revealing her glistening pink snatch and slipping a finger inside.

"You like what you see?"

Robert's cock was an iron rod pinned against his thigh by his jeans. "God yes."

"Truth or dare?" she whispered as she continued to play with herself.


She slid to her knees and crawled across the six feet separating the furniture, heavy tits hanging to the floor and swaying back and forth. Vicki sat back and watched her ass retreat, a look of intense desire on her face.

When she was in front of him she looked up and met his gaze. "Let me suck your cock."

She didn't wait for a response before rubbing her face into his crotch. He could feel the warmth of her mouth on his erection through the heavy denim as she kissed and sucked him through his jeans. She wrestled with his belt for a moment and finally pulled his pants down to his ankles. His engorged penis immediately sprang free.

"Mmmm," she purred. She gripped his towering cock and painted it with her tongue. Natasha's eyes, which were a piercing blue much like his own, bored into him as she slid his cock into her mouth.

"It's my turn again," he said. He let her continue bobbing on his cock for a few moments before leveling his gaze at Vicki. "Truth or dare?"

"Dare big boy."

"Let Natasha eat you out."

A mischievous smile flickered across her face. "Natasha dear, do you want to eat me?"

"Yes darling I do," she mumbled around Roberts cock. The pulled off of him with a pop and crawled across the floor.

She moved between Vicki's legs and pushed her skirt up around her waist and pulled a little black thong down her legs. She looked back at Robert and gave him a knowing look before burying her head in Vicki's crotch.

The moaning, slurping, sucking sounds coming from across the room were driving him crazy. His hand slid along his shaft as he anticipated how these women would taste. Vicki was staring intently at him, eyes shifting from his face to his cock hungrily. After a moment Natasha shifted to the side and Robert's hand stopped in mid stroke as his jaw hit the floor. She wasn't eating her out at all! She was sucking on a hard cock nearly as big as his own!

Slowly it dawned on him...the beautiful blonde sitting across from him was a shemale! He was surprised to find that his cock was harder now than it ever had been before as he watched Natasha greedily gobble Vicki's meat. He saw that they were waiting for his reaction and stood up. He casually strolled over to the love seat and sat beside Vicki. He reached over to grab her cock at the base and started to stroke it while Natasha proceeded to give her a nice wet blow job. With her free hand Natasha reached up and resumed stroking Robert's swollen meat.

Vicki leaned closer, lips parting slightly, and kissed Robert then. There was a moment when his body stiffened before finally relaxing as Natasha shifted the focus of her mouth from Vicki's cock to his own. He began to return Vicki's kiss in earnest, their tongues exploring each others' while Natasha alternated sucking their throbbing cocks.

After a few minutes Vicki stood up beside him. Her erection swayed just inches from his face as she stared down at him. Gently she put her hand on the back of his head and pulled his face into her crotch, rubbing her cock on his face. Tentatively he opened his mouth and let her slide her thick meat in.

He never in a million years dreamt he'd be doing this, but it was really turning him on; his cock was throbbing with its own detectable heart beat as Natasha continued her oral attention. He relaxed his jaw and took as much of her cock as he could. Seeing that he's enjoying it, Vicki started to fuck his mouth. Robert responded by grabbing her ass, pushing her deeper into his throat.

The need to penetrate one of the sultry vixens was immense. He pulled Natasha up off her knees and stood up in the loveseat in front of him to grind her beautiful little pussy into his face. His tongue snaked out to lap at her dripping slit. The taste and smell of her pussy was pure ecstasy. She grabbed his head and pressed it into her crotch as he continued to lick and suck at her

Vicki was standing in front of them now, stroking Roberts cock and spreading Natasha's thick saliva all over it. She slowly turned around and lowered herself, grabbing his prick and guiding the head up to her ass.

It was so tight. He felt her muscles clamp down hard as the head popped into her and she slowly sank down his shaft until every inch was buried inside of her. She held him there for what seemed like forever, and then slowly started to grind up and down his dick.

Natasha quickly resumed her position on her knees in front of the loveseat and started licking and sucking her friends' hard cock while it bounced and wagged in front of her, taking turns switching from sucking Vicki's cock to licking Robert's swollen balls.

"Mmm you like that tight ass big boy?" Vicki prompted. "You like how it feels around your cock?"

Robert grunted in response.

"I think it's my turn for some cock," Natasha decided.

Vicki stood up, letting his meat fall from her gaping ass hole, and pushed Robert onto his back. Natasha climbed on top of him and quickly slid him into her dripping wet pussy. She was so soft and plump it felt like he would keep sliding into her forever. Finally her plump ass came to rest against his thighs and she started to bounce up and down on his cock, kneading and mashing her massive tits as she did.

Vicki moved around behind her, her cock glistening with lube, and pushed it deep inside Natasha's ass with one swift, practiced motion.

Natasha screamed in a mixture of pleasure and pain as two hard dicks filled and stretched her holes. "Oh! Yes! Fuck me! Stuff my holes with those fat cocks!"

Robert could feel Vicki's swollen member rubbing against his through the thinly stretched lining of Natasha's pussy. She leaned forward, letting her big natural tits hang in his face, smothering him.

I could die a happy man right now.

Natasha's moans grew louder and louder as they fucked her harder, pushing her toward the edge. Robert's balls were drenched from her juices and he can feel that she is getting close. He pressed his mouth to hers to stifle a scream as she started to cum, every muscle in her body clenching, squeezing the cocks being rammed into her. They continued to pound her as her orgasm rocked her body. Time slowed, as Natasha writhed and moaned in pleasure in his arms. His balls were pulled tight against his body, aching to be emptied. He wouldn't be able to last much longer. Seemingly reading his mind, Vicki pulled her cock out of Natasha's ass and stepped back. Natasha quickly rolled off him to her knees. Robert was on his feet in an instant. Natasha knelt between them, her head thrown back, mouth open, stroking one with each hand. Seconds later they came together, blowing hot loads of sticky cream over her waiting tongue. She slurped down every drop, licking both cocks clean.

With a full mouth she stood and pulled Vicki to her. Their bodies melted together as their mouths met. Thick white cum rained down on their gorgeous figures. Breaking the kiss, the women motioned for Robert to join them. He stepped close and their mouths met his as they shared a messy cum filled three way kiss.

""Why don't we all go take a shower?" Vicki suggested, wiping sperm from her smiling lips.

Natasha and Robert agreed in unison.

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