Shemale Surprise

SUMMARY: A married man is seduced and taken by a friend of his wife's.

EDITING THANKS: Thanks to Robert, goamz86 and MAB7991.

NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned.

*****

"You can stay with Robert if you wish," Mary said on the phone.

I looked up from my laptop where I was pretending to be working when, in reality, I was reading, for the hundredth time, the brilliant novella 'Shemale School: a Teacher Seduced'. The story had created a new obsessive fantasy I had never even considered before: to be with a Shemale.

I even contacted the authoress to tell her how much I enjoyed it, and have since became one of her editors. I had just finished editing a gay cocksucking story that, although I am not gay and have no interest in men, did have my mouth watering thinking of sucking a cock...which led me back to the Shemale story.

"No, no, he won't mind," Mary said, speaking for me like wives often do.

Seeing me looking at her perplexed, she just put her hand up as if to tell me she would explain when she got off the phone.

I shrugged and returned to the story as the main character in the story just comes to the realization that the headmistress of the school has a cock. I imagined Beverly a co-worker lifting up her skirt to reveal a cock, or my tomboyish sister-in-law Terry coming into my room during a visit and taking my ass with a surprise cock. Every time I see a beautiful woman now, I don't wonder if they are shaved or hairy. No, I wonder what the odds are that under that skirt, or inside those jeans, is a big cock looking for a place to get warm.

Hanging up, Mary said, "I have offered to let Mia share your hotel room this weekend."

"You have offered your hot friend to stay in a hotel room with me?" I repeated, surprised. Mia was easily her hottest friend with massive tits she loved to show off, was a major flirt and was, surprisingly, single.

"First of all, it would be better if you didn't refer to her as my hot friend," she said playfully, shaking her head.

"What should I call her, then?" I asked.

"Well, her name is Mia, so that seems a logical suggestion," she said coming over to me. I quickly logged out of the guest side of my computer, returning to my regular side, where it looked like I was searching Amazon for blu rays.

"I thought women liked when we gave more than one word answers," I quipped.

"You are insufferable," she said, joining me on the couch.

"I try," I shrugged. I love my wife. She is still as beautiful now as the day I met her. She has a ferocious sexual appetite and, unlike many of my married friends, the "I do's" didn't end the blow jobs, voyeuristic sex and anal sex, if anything I got more sex now after twenty-one years of marriage.

Her hand went to my stiff cock as she asked, "Is this because you were thinking of Mia?"

The truth was it was because I was reading Shemale porn but that didn't seem to be the correct answer. Although she knew I was kinky, I wasn't sure she needed to know that I fantasized about having sex with a Shemale. So I answered, trying to be suave, "I was just thinking it was time to make love to my beautiful wife."

"I call bullshit," she smiled, as she grabbed my computer, put it on the table and fished my cock out of my pants.

"Fine," I answered, deciding to tell her exactly what I was thinking about at the moment. "I was imagining Mia seducing me in my hotel room and surprising me with a big cock between her legs instead of a cunt."

Mary coughed, looking startled by my answer, as she stroked my stiff six inch cock. "Be careful what you wish for."

"So I have permission to have sex with Mia if she has a cock?" I asked, teasing her like I always did.

We had both talked about adding a third person to our sex lives, Mary has admitted she would love to be the centrepiece in a gang bang and I have said I would love to be in the middle of a pussy sandwich.

She bent over and took my cock in my mouth. After bobbing up and down for a couple of minutes, she answered, while stroking my cock, "Yes, if Mia has a cock between her legs, particularly an eight inch python, you are more than welcome to be her bitch."

"Oh God," I groaned, as Mary accidentally described my most constant fantasy.

"Would you suck her cock?" she asked, pumping my cock while swirling her tongue around my mushroom top.

"God, yes," I moaned, closing my eyes, the visual instantly coming alive.

"And you'd swallow her cum?" she asked, taking off her blouse and bra.

She often talked dirty, but usually while I was fucking her with her ankles crossed around her head (she is amazingly flexible), or pounding her ass (she loves the submissive situation of giving herself completely to me) or when I began talking dirty to her about taking her to a frat house to be gang banged (her biggest fantasy being to be at the centre of a massive orgy). My wife is a beautiful oxymoron: she has a baby face, is only 5'2, blue eyes, dirty blonde hair and looks like the normal next door mother of three that she is. On the outside she is conservative and no one would suspect the inner slut inside her. She almost never wears panties, leaving easy access to her shaved cunt, wears thigh high stockings under her seemingly conservative skirts and dresses, has voluptuous 38DD tits that added a forth fuck hole besides her mouth, cunt and ass.

I replied, as she leaned forward and started fucking my cock with her massive tits, literally milking my cock, "If she told me to."

"You fucking cocksucker," she accused, pumping my cock with her tits.

"Aaaah," I groaned, as I sprayed my cum between her voluptuous soft tits.

Mary laughed, "Well that was new."

"So it was," I sheepishly smiled. Sure, Mary had many times insinuated she would be game to a lesbian encounter, but I had never mentioned any interest in cock...even Shemale cock.

"One day we may have to live out some of these fantasies," Mary said, scooping cum from between her tits and putting it in her mouth.

"You first," I playfully smiled.

"So I have permission to eat cunt next weekend?" She asked, her question more brazen than usual.

"Eat away," I offered, the thought of my wife between another woman's legs making my cock start to stiffen again.

"So to be clear," she smiled, her hand back on my cock. "While you are at Jerry's wedding you have permission to have sex with a Shemale and I have permission at Carrie's wedding to have lesbian sex," she clarified.

"So it seems," I replied with a soft smile, as she continued stroking my cock. Both of us had weddings to go to on the same weekend. She was a bridesmaid to one of her best friends since high school and was flying to Ohio on Wednesday for the wedding. Meanwhile, my boss was getting married in the city and I really had no choice but to go.

I asked, "How does Mia fit into all this?"

"She is friends with the bride, apparently," Mary answered, standing up.

"I can't wait to suck her cock," I joked.

Mary replied, as she turned around and lowered herself onto my cock, "I bet she will be happy to hear that."

I laughed, "I bet she will."

She rode my cock for an eternity, as I just sat back and enjoyed the ride. Having already come once, I was in for the long haul and my mind pondered...what if Mia did have a cock?

"Want my ass, baby?" Mary cooed, bringing me back to reality.

"Of course, honey," I answered, loving how my wife believed every hole should be used in almost every love making session.

She got off me, laid on the couch beside me with her legs up and said, "Now fuck my ass hard, cocksucker."

Being called a cocksucker after the playful banter was another surprise, but I answered, as I stood up and positioned myself in front of her, "Just shut up, cunt licker, and take my cock in your ass like the slutty gangbang princess you wish you were."

"Oh, Robert," she moaned, loving the name calling once our fuck sessions got going, as I filled her ass with my cock.

"Taking cock after cock in all three of your fuck holes," I continued, knowing how much she loved the dirty talk when she was close to orgasm.

"Oh yes, plug my ass," she whimpered, close to orgasm, moving her hand to her clit.

"Come, my little ass slut," I demanded, slapping her ass.

Moments later she screamed as her orgasm coursed through her. I continued slamming into her until I had unloaded my cum in her ass.

Once both spent, cuddling on the couch, my cum leaking out of her ass, she said, her breathing still stunted from her orgasm, "One day soon we really need to make our fantasies a reality."

"Just say when," I smiled.

"When," she said back.

I looked at her and asked, "Are you serious?"

"If you want to, I'm game," she admitted.

"Craigslist?" I asked. We had read all the ads and considered replying so many times, but always chickened out. Yet, something in her eyes and tone told me this time was different.

"Set it up for after the weddings," she suggested. "I get my period in a couple of days."

I laughed, "Yeah, we should probably wait until that is over."

The next few days flew by and other than a quick blow job before she headed to the airport, we hadn't had sex since that crazy night.

After she was gone, I started going through Craigslist listings and contacted a couple dozen potential couples. After a few back and forth emails with seven couples I had it narrowed down to three potential couples...which I would show Mary once she got back.

Thursday evening, Mia called me, "Hey Robert, surviving all alone?"

I answered, "The house is eerily quiet."

"What does a man do when he is home alone," Mia asked.

"Watch porn," I joked, although truthfully it wasn't a joke.

"What kind?" Mia asked, always very frank when we chatted.

"All kinds," I answered, not wanting to admit I was watching mostly Shemale porn.

"So, I was wondering if I could catch a ride tomorrow," Mia asked, thankfully dropping the subject.

I quipped, playfully, "Since we are already going to be sleeping together, we might as well ride together."

Mia, a nasty flirt like me, countered, "Oh, I plan on using you for rides all weekend long."

I joked, "Be careful. I could take that the wrong way."

Mia's voice dripping with sexuality countered, "You can take that any way you want to."

I stammered, "I-I-I am leaving from work at three."

"I'll meet you there," she said.

"Ok I could come and get you," I offered.

"No, no," she said, "I don't want to be an extra burden on you."

"Trust me, you're not a burden," I said. "A pain in the ass, sure, but not a burden."

"Oh remember those words Robert," she said ominously, before adding, "I got to go, stud. See you tomorrow."

"Okay, bye," I said, hanging up...my cock stiff as a missile. I instantly clicked on some of my downloaded Shemale porn and as a big cocked dark skinned Shemale face fucked a man in a suit in his office, I fantasized the man being me and the Shemale being Mia. I shot my load in seconds before going to pack.

...

Mia arrived at my office a few minutes early dressed in an incredibly provocative and sultry outfit for a three hour drive. She wore a light blue dress a couple inches below the knee, beige nylons, my fetish being nylons, and five inch heels, which were ridiculously high to wear anytime, but particularly ridiculous for a drive.

I asked, playfully, "Hoping to get lucky on the drive?"

"Always look your best I say," Mia answered.

"It's a good theory," I said, my cock already hard...Mia was a beautiful woman and knew exactly how to flaunt her very sexy assets.

"Ready to go?" She asked.

"Sure," I said, shutting down my computer.

The first hour of the drive we talked about work, love and politics. What made Mia more impressive was she was the full package. She was beautiful, funny and intelligent. The only other woman who I thought met all three of those requirements, I married.

"I need to pee," she announced.

"Good to know," I answered.

"Could we please stop at the next town, smart ass," she said, slapping my leg.

"I could use a coke," I agreed, pulling in a few minutes later at a small gas station.

After our pit stop, we were back on the road when Mia slipped out of her heels. "I hope you don't mind, but my feet are killing me," Mia said, as she leaned her chair back and put her stocking-clad feet on the dash of the car.

I looked at her red painted toenails through the sheer nylon, and my cock stiffened. I loved nylons, and I particularity loved toes in nylons. It is a strange fetish, but it was what turned me on.

I said, "I don't know why women try to kill themselves with such foot wear."

"It's all a part of the illusion," Mia answered.

Glancing over, I realized that her long legs were going to be a constant distraction, way more dangerous than playing with a cell phone. I noticed that her nylons weren't pantyhose, but stockings, seeing the top of her stockings being held up by a garter-belt. The sight was easily one of the hottest I had ever seen in person. It was going to be a tough weekend to behave.

"W-w-what illusion?" I stammered.

"The allure of the woman," she answered, her tone sultry, her answer vague.

"Half sentences don't really answer the question," I pointed out.

She wiggled her toes, causing me to leer way longer than socially acceptable and not an overly safe thing to do while going 65 on the highway.

The heels are part of the full ensemble," she continued, before saying, her tone shifting to regret, "although most women have gotten lazy and think doing half the job is okay."

"Half the job?" I asked, trying to focus on the road and not Mia's lovely legs and feet.

"Yes, men are so easily turned on, most women just wear heels or a tight blouse, or a short skirt, but not the entire package," she explained, shifting her legs again, making it impossible to ignore them.

"Tell me about it," I sighed, having noticed myself the rarity of women in nylons in 2014.

"That was a heavy sigh," she noticed. "Do tell."

"I'm a leg man and over the years the popularity of pantyhose has declined at an alarming and disappointing rate," I said, still trying desperately not to stare at her legs.

"Exactly my point," she said, as she moved her hand to adjust a garter on her left leg. She continued talking as if such an act wasn't quite likely to cause a major collision. "The whole package means accentuating every asset. On the outside you dress sexy, but classy. The outfit should showcase a woman's breasts, ass and legs. High heels and nylons help enhance the sensuality and sexuality of a woman."

"Can't argue with that," I said, smiling at her as I checked out her long legs once again.

"In theory, a woman's outside look should be alluring, while underneath the outer layer is a sexual being," she continued.

"So dress like a lady on the outside and a slut on the inside," I clarified.

"That makes it sound dirty," she said, annoyed by my simplistic analysis of her theory.

"I'm sorry," I quickly apologized.

She laughed, "I'm just kidding, it pretty much is that simple. The key is to get every man to want to fuck you and every woman to want to be you."

"Well, I think it is working," I said, again leering way too long at her legs and feet.

"You want to fuck me?" She asked, her tone sultry, her smile playful.

"If I was single I would devour you whole," I quipped back, our flirting reaching a whole new level.

"Hmmm, remember those words," she smiled, her tone ominous again.

"Hmmm, right back at you," I replied, trying to sound manly even though I was confused by her tone.

Changing topics, after a brief awkward silence, she said, "Mary told me you're a leg man."

"That I am," I nodded, staring at the road, desperate to not look at her legs after such a statement.

"Especially in nylons," she added, moving her legs slightly, which I noticed out of my peripheral.

"What else do you two talk about?" I asked.

"Everything," she answered.

"That's a pretty wide scope," I said, my eyes darting to her nylon-clad toes.

"Our conversations tend to meander," she admitted.

Thinking that is how all women's conversation went, I asked, "What else do you know about me?"

"Don't ask questions you don't want to know the answer to," she teased.

"Fair enough," I laughed.

We drove in silence for a while before she asked, "Do you think Mary will eat cunt this weekend?"

I coughed as I asked, "Where did that come from?"

"She told me you gave her permission to eat pussy and she gave you permission to have sex with a Shemale," she revealed.

My face burned with embarrassment. I replied, "That was just heat of the moment talk."

"Mary has wanted to eat pussy forever," Mia said, so matter-of-factly that it seemed inevitable.

I quipped, "She wants to be gang banged too, but fantasy is fantasy."

"But what if fantasy could become reality?" she asked, her tone suddenly serious.

"It's a dangerous line to cross," I said, knowing that fantasy stayed fantasy for a reason.

"Would you seriously let her if the opportunity arose this weekend?" she asked.

"I don't know," I admitted, the conversation at the time I gave her permission was rather laissez faire.

"And if a Shemale came to you this weekend and offered herself to you, would you take her up on the offer?" Mia asked.

I laughed, "Like that is likely to happen."

"That isn't the point, would you?" she asked again.

"Would you?" I questioned back.

"I have before," she revealed.

"Really?" I asked, surprised.

"Of course, Shemales are the perfect specimen. The beauty of a woman; the sophistication of a woman; the upper body of a woman; and yet the lower equipment of a man, which, let's be honest, the only body part that is sexier on a man is his penis...cunts are incredibly unattractive," Mia said, her face squishing up like she had just sucked on a lemon.

"At least I know you're not a lesbian," I joked.

"God no," she said.

"Tell me how you really feel," I joked.

"I love cock," she answered, talking to me as a guy and not as her friend's husband.

I joked again, repeating the same words, "Tell me how you really feel."

"No, seriously," she said. "All cunts look the same, I can't imagine trying to pick one out of a pussy line-up."

"I'd be willing to try," I quipped.

"On the other hand, every cock is distinctly different," she continued, ignoring my interjection.

"Like no two snowflakes are alike," I pointed out.

"Exactly," she said. "There are big ones, small ones, thick ones, curved ones," she listed.

"Black ones," I joked.

"Not all black cocks are huge, trust me," she said. "Actually, the biggest three cocks I have ever seen are all white. Although I have seen some impressive black cocks, too."

I couldn't resist, "You're quite the cock-connoisseur," playing on the word connoisseur.

"Says the guy obsessed with Shemales," she quipped right back.

"Obsessed is a strong word," I countered.

"Semantics," she shrugged. "Hey, you never answered my question."

"Which was?" I asked, the conversation taking so many twists and turns I couldn't remotely recall the question.

"If a Shemale threw herself at you, would you go for it?" she asked.

"I don't know," I answered, which was a true answer.

"But your wife gave you permission," she pointed out.

"But she wasn't serious," I pointed out.

"Wasn't she?" she asked.

"Fine," I said. "If a Shemale hits on me at the wedding tomorrow, I will take her back to my room."

"And suck her cock?" Mia asked playfully, again wiggling her toes which continued to keep my cock hard.

"Fine," I said exasperated by the strange conversation. "I'll suck her cock."

"How about that sexy ass of yours, Robert, would you give that up, too?" she asked, teasing me relentlessly.