Synopsis: A married man is seduced by a friend of his wife.
Editor’s Thanks: Thanks to Robert, golz86 and mab7991.
NOTE: This story is dedicated to Robert, who asked for the spec… Sorry, but the story turned out to be much longer than originally planned.
*****
“You can stay with Robert if you want,” Mary said over the phone.
I looked up from my laptop and pretended to work, while in reality I was reading the wonderful novel “The School for Shemales: The Seduced Teacher” for the hundredth time. This story created a new obsessive fantasy that I had never thought of before: being with a shemale.
I even contacted the author, told him how much I loved the book and have since become one of his editors. I just finished editing a lesbian blowjob story that, although I’m not gay and have no interest in men, still made me crave cock sucking… which brings me back to the shemale story.
“No, no, he won’t mind,” Mary said for me, as wives often do.
Seeing me looking at her confused, she simply raised her hands as if telling me she would let me know when she hangs up.
I shrugged and went back to the story, in which the main character had just realized that the school principal had a dick. I imagined Beverly as a co-worker lifting up her skirt to reveal a cock, or my tomboy sister-in-law Terry fucking my ass with a surprise cock when she came into my room. Now whenever I see a beautiful woman, I don’t question whether they are shaved or hairy. No, I want to know if there is a big cock looking for a warm spot under that skirt or inside those jeans.
After hanging up, Mary said, “I’ve offered Mia to stay in a hotel room with you this weekend.”
“Are you inviting your sexy friend to stay in a hotel room with me?” I repeated in surprise. Mia is easily his sexiest friend, she loves to show off her big tits, she’s a big flirt, and surprisingly, she’s single.
“First of all, you better not call her my hottie,” he said, shaking his head jokingly.
“Then what do I tell him?” I asked.
“Well, her name is Mia, so that seems like a logical suggestion,” he said, walking toward me. I quickly logged out of the guest side of my computer and returned to my regular side, where it looked like I was searching for Blu-rays on Amazon.
I quipped, “I thought women liked it when we gave more than one-word answers.”
“You’re so insufferable,” he said, joining me on the couch.
“I’ll try,” I shrugged. I love my wife. She’s as beautiful today as she was the day I met her. She has a strong sexual desire, and unlike many of my married friends, “I do” doesn’t end with oral sex, voyeur sex, and anal sex, and if anything, I have more sex now after twenty-one years of marriage than I do. Behavior.
She reached for my stiff cock and asked, “Is it because you’re thinking about Mia?”
The truth is, it’s because I’ve been reading shemale porn, but that doesn’t seem like the right answer. Although she knew I was weird, I wasn’t sure she needed to know that I fantasized about having sex with a shemale. So I answered as politely as possible: “I just thought it was time to make love to my beautiful wife.”
“I call bullshit,” she smiled, grabbed my computer, put it on the table, and pulled my cock out of my pants.
“Okay,” I replied, deciding to tell her exactly what I was thinking at the moment. “I thought about Mia seducing me in my hotel room and surprising me with a big cock between her legs instead of her pussy.”
Mary coughed while stroking my hard six-inch penis and seemed surprised by my response. “Be careful about your wishes.”
“So if Mia has a dick, can I have sex with her?” I asked, teasing her as usual.
The two of us discussed adding a third party to our sex life, Mary admitted she would love to be the centerpiece of group sex and I said I would love to be the centerpiece of a pussy sandwich.
She bent down and took my cock into her mouth. After bobbing up and down for a few minutes, she replied while stroking my cock, “Yes, if Mia has a cock between her legs, especially an eight inch python, you are welcome to be her bitch.
“Oh my god,” I moaned as Mary inadvertently described my most frequent fantasy.
“Would you like to suck his cock?” she asked while jerking my cock and moving her tongue around the tip of my cock.
“God, yes,” I groaned, closing my eyes as the scene instantly came to life.
“Will you swallow his cum?” she asked as she removed her shirt and bra.
She talks dirty a lot, but usually when I’m fucking her with her ankles twisted above her head (she’s very flexible), or spanking her ass (she loves giving herself over completely to me in my submissive position), or when I started talking dirty and talked about taking her to a frat house to be gang-raped (her biggest fantasy was to be the center of a massive orgy). My wife is a beautiful paradox: she has a baby-faced face, she’s only 5 feet 2 inches tall, blue eyes, dirty blonde hair, and she looks like a typical neighborhood mother of three. She’s so reserved on the outside that no one would suspect her inner slut. She almost never wears panties to provide easy access to her shaved pussy, wears thigh-high stockings under her conservative-looking skirts and dresses, and she has sexy 38DD tits that make her mouth, pussy, and ass a fourth fuck hole.
As she leaned forward and began fucking my cock with her huge tits, I replied, “If she would have told me.”
“You bastard,” she accused, using her breasts to pump my cock.
“Aaaahh,” I groaned, spilling my cum between her sexy, soft breasts.
Mary laughed and said, “Well, this is something new.”
“I see.” I smiled coyly. Of course, Mary had hinted several times that she would be interested in lesbian encounters, but I had never expressed any interest in cocks… even shemale cocks.
“One day we’ll have to live out some of these fantasies,” Mary said, scooping up some of the cum from between her breasts and popping it into her mouth.
“You go first.” I smiled playfully.
“So I have the right to eat pussy next weekend?” she asked, her question even more cheeky than usual.
“Eat it,” I offered, my cock beginning to stiffen again at the thought of my wife between another woman’s legs.
“To be clear,” she smiled, placing her hand back on my cock. “You had the right to have gay sex when you were at Jerry’s wedding, and I had the right to have gay sex at Carrie’s wedding,” she clarified.
“Guess so,” I replied with a slight smile as she continued stroking my cock. We were both attending a wedding on the same weekend. She was the maid of honor for one of her best friends since high school and flew to Ohio for the wedding on Wednesday. At the same time, my boss was getting married in town and I really had no choice but to go.
I asked, “How does Mia fit into all of this?”
“Apparently, she’s a friend of the bride,” Mary replied, standing up.
I joked, “I can’t wait to suck his cock.”
Mary turned and positioned herself on my cock and replied, “I’m sure she’ll be happy to hear that.”
I laughed, “I’m sure she does.”
She rode my cock for what seemed like an eternity and I just sat back and enjoyed the ride. Having already come once, I had been waiting a long time and my mind was wondering… what if Mia actually had a dick?
“Want my ass, baby?” Mary said, bringing me back to reality.
“Of course, honey,” I replied, loving the fact that my wife believed that almost every hole should be used whenever we had sex.
She moved off of me, lay down on the couch next to me, crossed her legs and said, “Now fuck my ass harder, asshole.”
It was another surprise to be called a “jerk” after the joke, but as I stood up and faced her, I responded: “Shut up, lick that pussy, put my dick in your ass, like a slutty gangbang princess all you want.
“Oh, Robert,” she moaned as our sex session began, loving the name as I filled her ass with my cock.
“Put that cock in all three of your holes,” I continued, knowing how much she enjoyed dirty talk when she was close to orgasm.
“Oh yes, fill me up in my ass,” she whimpered, moving her hand to her cunt as she reached her climax.
“Come on, my little slut,” I demanded, slapping her ass.
After a while, she screamed as her orgasm passed through her. I continued to pound her hard and fast until I shot my load inside her ass.
As the two of us cuddled together on the couch, my cum oozing out of her ass, she said, her breathing still labored from her orgasm, “One day soon we really need to make our fantasies a reality.”
“Just tell me when.” I smiled.
“When,” he answered.
I looked at him and asked, “Are you serious?”
“I do, if you do,” she admitted.
“Craigslist?” I asked. We read all the ads and considered responding several times, but always demurred. However, her eyes and tone told me this time was different.
“Schedule it for after the wedding,” she suggested. “I’ll get my period in a few days.”
I laughed and said, “Yeah, we should wait until that thing’s over.”
The next few days passed quickly and other than a quick blowjob before leaving for the airport, we hadn’t had sex since that crazy night.
After she left, I began browsing Craigslist and contacted dozens of potential couples. After a few back-to-back emails with seven couples, I narrowed it down to three potential couples…whom I will show Mary as soon as she gets back.
Thursday night, Mia called me, “Hey Robert, are you surviving alone?”
“The house was very quiet,” I replied.
“What do you do when you’re home alone?” Mia asked.
“Watching porn,” I joked, though honestly it wasn’t a joke.
“Which one?” Mia asked, she was always clear when we talked.
“All kinds,” I replied, not wanting to admit that I mostly watch shemale porn.
“So, I was wondering if I could get a ride tomorrow,” Mia asked, thankfully dropping the topic.
I joked: “Since we’re going to sleep together, let’s ride bikes together.”
Mia, who hates flirting as much as I do, replied, “Oh, I’m going to use you for outings all weekend.”
I joked, “Be careful. I might misinterpret this.”
Mia’s sexy voice replied: “You can do it either way.”
I stammered: “I get off work at three.”
“I’ll meet you there,” she said.
“Well, I can carry 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. “It’s definitely painful, but it’s not a burden.”
“Oh, remember this Robert,” he said ominously, then added, “I gotta go, man. See you tomorrow.”
“Okay, bye,” I said and hung up…my cock was as hard as a missile. I immediately clicked on some shemale porn I had downloaded and as a big cocked dark skinned shemale fucked a man in a suit in his office, I imagined the man was me and the shemale was Mia. I shot my load in seconds before packing up.
……
Mia arrived at my office a few minutes early wearing an extremely provocative and sexy outfit and drove for three hours. She wore a light blue dress that ended a few inches below the knees, beige nylon, my favorite thing about nylon, and five inch heels, which were ridiculously high when worn at any time, but especially ridiculous for driving.
I jokingly asked, “Would you like some luck while driving?”
Mia responded, “I say, always look your best.”
“That’s a good theory,” I said, my cock already hard… Mia is a beautiful woman and knows how to show off her extremely sexy assets.
“Ready to go?” he asked.
“Of course,” I said, shutting down the computer.
We spent the first hour of driving talking about work, love and politics. What impressed Mia even more was her full bag. She is beautiful, funny and smart. I think she is the only woman who meets all three of these requirements that I have married.
“I need to pee,” she announced.
“Good to know,” I replied.
“Can we stop in the next town, smart guy,” he said, patting my leg.
“I could use a Coke,” I agreed, and a few minutes later I stopped at a small gas station.
Mia slipped as we got back on the road after the pit stop. “I hope you don’t mind, but my feet are killing me,” Mia said, leaning back in her chair and placing her stockinged feet on the car’s dashboard.
I looked at her red painted toenails through the clear nylon and my cock stiffened. I love nylon, especially nylon toes. It’s a strange obsession, but that’s what turns me on.
I said, “I don’t understand why a woman would commit suicide wearing shoes like that.”
“It’s all part of the illusion,” Mia replied.
Looking back, I realized that her long legs were a constant distraction, which was even more dangerous than her playing with her phone. I noticed that she was wearing stockings, not nylon pantyhose, and I noticed that the top of her stockings were held up by garters. This is one of the most seductive scenes I have ever seen. This is going to be a tough weekend to perform.
“What hallucinations?” I stammered.
“A woman’s charm,” she replied, her tone sexy and her answer vague.
“Half a sentence doesn’t really answer the question,” I pointed out.
She curled her toes and slanted her eyes at me for longer than the socially acceptable limit, and that’s not exactly a safe thing to do at 65 miles on the highway.
Heels are part of the whole outfit,” she continued, before her tone turned to regret, “even though most women get lazy and think that doing half the work is enough.
“Half done?” I asked, trying to focus on the road rather than Mia’s adorable legs and feet.
“Yes, men get aroused easily, and most women only wear heels or tight tops or skirts, but not full outfits,” she explained, moving her legs again so they couldn’t be ignored.
“Tell me,” I sighed, noting that women wearing nylons were rare in 2014.
“It was a heavy sigh,” she said. “You have to tell me.”
“I’m a leg freak, and over the last few years pantyhose have declined in popularity at an alarming and depressing rate,” I said, still trying my best not to stare at her legs.
“That’s exactly my thing,” she said, adjusting the garter on her left leg with her hand. She continued, as if such behavior was unlikely to cause a major confrontation. “An outfit is meant to accentuate every asset. On the outside, you dress sexy, but elegantly. Clothing should show off a woman’s breasts, hips and legs. High heels and nylons help to enhance a woman’s sensuality and sexuality.”
“Can’t deny that,” I said, smiling at her and taking another look at her long legs.
“Theoretically, a woman’s appearance should be attractive, but underneath that outer layer is a sexy creature,” she added.
“So dress like a lady on the outside and a slut on the inside,” I explained.
“That sounds dirty,” he said, annoyed by my simplistic analysis of his theory.
“I’m sorry.” I apologized immediately.
She laughed: “I was just joking, that’s all. The point is that every man wants to fuck you and every woman wants to be like you.”
“Well, I guess this works,” I said, taking another long look at her legs and feet.
“Do you want to fuck me?” she asked, her voice sweet and her smile playful.
“If I were alone, I’d eat you whole,” I quipped, taking our flirting to a whole new level.
“Well, remember those words,” she smiled, her tone turning ominous again.
“Well, right here with you,” I replied, trying to appear manly even though I was confused by his tone.
After a few moments of awkward silence, she changed the subject and said, “Mary told me you were a one-legged man.”
“That’s just me,” I nodded, staring out at the road, desperate not to look at his feet after saying it.
“Especially the nylon ones,” she said, shuffling her feet a bit, which I noticed from my surroundings.
“What else are you two talking about?” I asked.
“Everything,” he replied.
“That’s pretty wide,” I said, glancing at her nylon clad toes.
“Our conversations are sloppy,” she admits.
I thought all women talked this way and asked, “What else do you know about me?”
“Don’t ask questions you don’t want to know the answers to,” he joked.
“That’s right,” I said, smiling.
We drove in silence for a while and then he asked, “Do you think Mary is going to eat pussy this weekend?”
I coughed and asked, “Where did that come from?”
“She told me you allowed her to eat pussy and she allowed you to have sex with shemales,” he revealed.
My face turned red with embarrassment. I replied, “It’s just a hot topic.”
“Mary’s always wanted to eat pussy,” Mia said, so matter-of-factly that it seemed inevitable.
I quipped, “She also wants to be gang-raped, but fantasies are fantasies.”
“But what if fantasy becomes reality?” he asked, his tone suddenly serious.
“It’s a dangerous line to cross,” I said, knowing that fantasies remain fantasies for a reason.
“If you had the chance this weekend, would you really let him do that?”
“I don’t know,” I admitted, opening up the conversation as I gave him permission.
“If a transgender person comes to you this weekend and proposes to you, will you accept it?”
I laughed and said, “It’s very possible.”
“That’s not the point, is it?” he asked again.
“Do you know how?” I asked.
“I’ve had it before,” she revealed.
“Really?” I asked in surprise.
“Of course, shemales are the epitome of perfection. The beauty of a woman, the fragility of a woman, the upper body of a woman and the lower body of a man, honestly, it’s the only part of the body that can be expressed. What’s more sexy about a man is his penis… the vagina is very unattractive,” Mia said, her face scrunched up like she had just sucked a lemon.
I joked, “At least I know you’re not gay.”
“God no,” she said.
“Tell me how you really feel,” I joked.
“I like cock,” she replied, speaking to me as a man rather than her friend’s husband.
I joked, repeating the same words again, “Tell me how you really feel.”
“No, seriously,” he said. “All pussies look the same and I can’t imagine trying to pick one out from a line.”
“I’d love to try,” I quipped.
“On the other hand, every cock is completely different,” she continued, ignoring me.
“Just like no two snowflakes are alike,” I explained.
“Sure,” she said. “There are big ones, small ones, thick ones, curved ones,” she listed.
“Black people,” I joked.
“Not all black cocks are big, believe me,” she said. “In fact, the three biggest cocks I’ve ever seen were all white. I’ve seen some impressive black cocks too, though.”
I couldn’t stop myself from saying, “You’re a huge cock connoisseur,” using the word “connoisseur.”
“Says the guy who’s crazy about transgenders,” he quipped.
“Obsessed is a strong word,” I retorted.
“Semantics,” he shrugged. “Hey, you never answered my question.”
“Which one is that?” I asked, the conversation taking so many turns that I couldn’t remember the question.
“If a ladyboy jumped on you, would you chase her away?”
“I don’t know,” I replied, and it was a truthful answer.
“But your wife gave you permission,” she pointed out.
“But she wasn’t serious,” I pointed out.
“Isn’t he?” she asked.
“Okay,” I said. “If a monster attacks me at the wedding tomorrow, I’ll take it back to my room.”
“And suck his cock?” Mia asked, wriggling her toes again, which kept my cock hard.
“Okay,” I said, annoyed by the awkward conversation. “I’ll suck his cock.”
“Robert, what about that sexy ass of yours, are you ready to give it up too?” she asked teasing me mercilessly.
