tagTransgender & CrossdressersJennifer's Surprise

Jennifer's Surprise

byAnn Douglas©

"This trip has been a waste!" Jennifer said to herself as she signaled to the bartender for a refill on the drink.

Go to the Club Med on Martinique, the travel agent had said. Its one big party with great guys all over the place. Seven days of fun and sun.

Well she'd been here four days and all the guys he's met were wither hopeless jerks or ego tripping jocks looking for an easy lay. If she wanted to meet guys like that she could've stayed home.

"Excuse me, mind if I sit here?" said a voice from behind Jennifer.

Looking up, Jennifer saw the voice belonged to a tall woman of about 30, dark haired and slightly Hispanic in her features. She wore a small bikini top which barely contained her 36" breasts and a short blue skirt.

"I know there are still some empty tables, but if I sit alone I'll have some guy hitting on me before I can even get a drink." Jennifer smiled and motioned to the empty seat across from her.

"Thanks" the older woman said as she settled into the chair and signaled for a drink.

"Jennifer Carson from New York" the 19 yr. old said as she brushed back her brown hair.

"Jade Martinez of San Jaun ," answered the woman as the bartender placed her drink before her.

"You're right about the guys," Jennifer said. "I've been hit on by so many assholes these last four days that I'm seriously thinking of going home early."

"Oh don't do that, I'm sure if you hang in there you'll find someone."

"Maybe..." Jennifer said.

The conversation went on as they learned more about each other. An hour and several drinks later, Jennifer decided she truly liked this woman. It wasn't anything she could put her finger on but there was definitely something.

"Oh shit!" said Jennifer in a low voice as she noticed her roommate crossing the bar. "Not again."

"What's the matter?" Jade asked.

"That's my roommate," she answered as she pointed to the giggling blonde crossing the dance floor with one of those "jocks". "It's been like this every night. She meets some asshole jock and winds up back at our room humping his brains out. Then I wind up spending the night camped out on the beach or in a lawn chair. I'm really getting tired of this."

"Can't you discuss it with her," Jade asked. "Did she come here with you?"

"Never met her before the day I got here. I came on a package plan, you have to have two to a room. They just matched us up when we got off the plane. I tried talking to her and her only response was that if I wanted to I was more than welcome to join in the fun. Given the selection I don't think I'm going to ever get that desperate."

"Well...maybe you can switch rooms."

"I tried that, they said they had no other requests for switches and there's no way I could afford the upgrade to a single room."

"Hmmmm..."Jade said as she ran her tongue across her red lips. "I have a single and its really a lot more room that I need. If you like you can move in with me. I can promise I won't be bringing any if those guys back to my room at night."

"I don't know..." Jennifer said, running her fingers across the top of her drink.

While she thought it over, Jennifer took a good look at the woman on the other side of the table. She was pretty sure Jade was being more than honest when she said she wouldn't be bringing any guys back to the room. Several times during their conversation, she had noticed Jade staring at her breasts, much the same way guys did. The idea that she might be a lesbian or at least bisexual didn't bother Jennifer. A few years before she had experimented with bisexuality during a vacation and found it not unpleasant. She hadn't followed up on it when she got home because she was afraid that none of her friends would ever understand. But here, no one knew here, she could be anyone she wanted.

"Oh what the hell..." Jennifer said out loud. "Why not."

"Wonderful!" Jade exclaimed. "I know you'll love it."

"To new friends..." Jennifer said as she raised her drink.

"...and new experiences." Jade added.

They finished their drinks and moved off to dinner. A quick stop at Jennifer's room afterwards took care of her luggage and they dripped it off at Jades.

"Lets leave it all for later, Jenn, " Jade said as they dropped the suitcases on the couch. "Lets go dancing."

So off they went, dancing the night away on one of the discos. Since there were plenty of women dancing together, no one gave them a second look. Dancing with Jade, Jennifer was now positive that the night would end with them sharing more than the same bed. She found that she was now looking forward to it.

Jade entered the room first, turning on the light. Then as Jennifer followed, the older woman dimmed it to half its brightness.

"Do you want another drink? Jade asked with a wide smile.

"Not unless you want me to fall fast asleep." Jennifer answered.

"Oh, definitely not..." Jade countered as her smile drew larger.

Moving to Jennifer's side, Jade brushed her long brown hair away from her face. Lightly holding the sides of the smaller woman's face, she pulled Jennifer closer and kissed her.

Jennifer made no attempt to break the kiss, having made up her mind earlier to enjoy Jade's pleasures. She opened her mouth and was rewarded as Jade's tongue found hers.

A long series of small kisses followed as they explored each other, tasting the scent of each other's bodies. Jade continued onto Jenn's neck and licked along the canals of her ears.

Finally, Jade broke the embrace and took a large step back, undoing the strings of her bikini top. Her large brown tipped breasts burst forward as the tightly bound garment fell to the floor. Running her long red fingernails across her breasts she gave them a playful squeeze.

"Do you like?" She asked as she pulled one upward and gave the dark nipple a lick.

Jennifer answered with a smile of appreciation. All of her girlfriends had breasts as white as her own, she found Jades darker skin highly exotic.

Reaching forward she replaced Jade's hand with her own, feeling the nipples harden at her touch.

"Mmmm" Jade murmured.

Lifting the breasts upward, Jennifer leaned forward and kissed them. Her tongue first caressing the nipples and then her mouth eagerly engulfing it. The warmth of Jennifer's mouth moved upward, depositing sweet kisses along Jade's body as it went. Returning to Jade's mouth, tongue once again found tongue as the two locked in a tight embrace.

Jade ran her hands down Jennifer's chest, undoing her blouse and pulling it off. She grabbed a breast in each hand and buried her face between them. Hot, wet kisses covered each nipple as the larger woman eased Jennifer back onto the bed. Without diverting her attention from her breasts, Jade pulled off both Jennifer's skirt and panties, leaving her naked.

No sooner had the panties hit the floor when Jade rammed her long slender fingers into the already wet pussy.

"Oooohh!" Jennifer sighed as Jade moved her fingers in and out.

After a few more strokes, Jade joined her fingers with her tongue and began licking the hot pussy with reckless abandon.

"Oh yes!...Suck that pussy!" Jenn yelled as she held onto Jade's head and drove her dripping cunt into a more than eager mouth.

In minutes, Jennifer was bouncing like a cat in heat, she'd never had her pussy licked like this . No man or woman had ever approached Jade's skill with her tongue.

Jenn was so lost in ecstasy she didn't notice at first when Jade slid a pussy wet finger into her ass and began fucking that. After a few strokes that began to drive Jennifer even wilder.

"God, I wish I had a dildo!" She yelled as she felt yet another explosion building inside her. "I want to be fucked until I drop!"

Suddenly, Jade stopped and took a step back... It was a few seconds before Jennifer realized she had stopped.

"I'm sorry..." She panted." Please don't stop...That was the most incredible pussy licking I've ever had."

Jade turned around and bent over, removing her skirt and panties. With her back still to Jenn she ran her fingers across her soft tanned ass.

"Oh..." Jennifer said. "I guess its my turn to eat some pussy." she added with a smile.

"Not exactly..." Jade said as she started to turn around.

Jennifer's eyes and mouth both jumped open when Jade turned all the way around. Suspended between the legs of this incredibly beautiful woman was a cock and balls. At first she thought they were fake but then realized they were the real thing as the limp cock was already beginning to harden.

"I don't fucking believe this! Jenn said as she moved to get a closer look.

"I hope you're not disappointed." Jade said.

Jennifer had once seen a sex film that had featured a transsexual, so she knew Jade wasn't really a guy. In fact if anything, she was more woman than any of her girlfriends back home.

"Aren't you going to say anything?" Jade said in hesitation. A slight fear in her voice that said that she was afraid that Jennifer was going to turn and run.

Instead Jennifer reached forward and grabbed the erecting cock. She licked the tip a few times and then swallowed it whole. Her head surged back and forth as she buried her fingers into Jade's ass cheeks, bringing her cock to a rock hardness.

Now it was Jade's turn to moan in ecstasy as Jennifer gave both her cock and balls her undivided attention. If she was nothing else, Jenn was a champion cock sucker.

Several times she brought her to the edge if climax, but stopped just short of ejaculation. Not that she minded a mouthful of cum, she just had other plans.

Releasing the cock, she dropped back onto the bed and spread her legs giving Jade a full and unobstructed view of her still wet pussy.

"I want you to fuck me..." She said as she rubbed her pussy. "I want you to fuck me so hard that they'll hear me cum on the other side of the island!"

Without a moment's hesitation, Jade joined her on the bed and lifted the girl's legs into the air. With a single thrust she drove her seven inch cock deep within her, repeating it twice before Jennifer could catch her breath.

Dropping atop the smaller girl, she covered her mouth with her own , never stopping her pelvic thrusts. This time the kiss was savage, drawing a drop of blood as she bit down on Jennifer's lip. Moving downward she attacked Jenn's breasts with the same animal intensity. The small pink nipples disappeared into Jades mouth as she alternated between sucking and biting. Fighting for breath, Jennifer couldn't get out the words. She had passed any previous level of bliss, no man had ever fucked her as completely as this strange man-woman. She wanted it to go on forever.

"I'm... gonna... cum ..." She finally managed to whisper.

No sooner had the words been spoken than Jade pulled out and with a strength that caught Jenn by surprise, flipped her over onto her stomach. Then with an equally powerful thrust, Jade pulled Jennifer's pelvis into the air and reentered her pussy from the rear.

Now Jade became ever more forceful, lifting Jenn off the bed with each reentry. Both knew they couldn't hold off the explosion much longer, it was only the question of who would be first.

Deep inside her Jennifer felt the first burst of hot cum erupt from the cock deep within her. That was the final touch as her body exploded and her mind filled with bright lights. Her mouth opened to scream but no sound emerged, there was no energy left as she collapsed onto the bed in a sweat covered heap. Followed a second later by Jade.

Time stood still as their love juices mixed and dripped down their bodies. Both were too completely exhausted to break the embrace they had collapsed into.

Finally Jade broke the silence.

"I wasn't sure how you were going to take this..." She said. "But you were so pretty I had to take the chance."

Jennifer's only reply was a small smile as she rolled herself from under Jade and propped herself up on a pillow.

"It was a shock for a moment," She said. "but there is something you can do to make it up to me."

"And what would that be?" Jade asked with hesitation , wondering if she had made a dreadful mistake in trusting the girl.

"Do it again..." Jennifer said as she smiled ever wider.

END

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