Double Your Pleasure

Ken and I laid in bed together, both spent from the crazy evening of sex we had just finished. We were cuddling and my head was on his chest. He was stroking my hair, nuzzling me. "Maria?" he said.

"What's up hot stuff? I can tell from your voice you have something on your mind."

"Do you remember that dominatrix, Mistress Nicola, from our Las Vegas trip?"

"Of course, silly. I'm the one who hired her. Why are you asking about her?"

"Wellllll, it's not about her exactly. I just can't get the picture of you sucking one dildo while she pounded your ass with another dildo out of my mind. When I came that night while I was masturbating and watching the two of you, it was one of the most incredible orgasms I've ever had."

"And...."

"And-I-was-wondering-if-you'd-be-willing-to-suck-and-fuck-two-guys-while-I-watched-and-jerked-off?" He said this so quickly I wasn't sure I'd heard him.

"Did I hear you right? You want me to have sex with two guys while you watch? And masturbating while you watch the three of us? Seriously?"

"Yes!" He said this sheepishly but without hesitation.

"Wow, just wow!" was all I could reply. While I've had sex with other men (and Mistress Nicola!), I had never had sex with more than one person at a time. I didn't know what to think about Ken's request. My mind was racing, thoughts jumbled with confusion. "Ken, you've got to give me some time to think about this! I know I've told you in the past that you'd be in control, but I meant when the two of us were having sex. This is something completely different!"

A few weeks had gone by, and I hadn't been able to get Ken's request out of my mind. Could I do this? Did I want to do this? Let's face it. It's not exactly like I have a 'normal' sex life. I don't sleep with my wife very often, she's just not that interested. But as crossdresser Maria, I've had sex with men and I was basically having an affair with Ken, who was also married and happened to be a co-worker and friend of my male self, Luke. Maria and Ken's sex life was amazing. We were good together; we wanted to please one another and never came up short in that department! I've been monogamous my whole life. I've never cheated on my wife as Luke; and Maria had never slept around either. She'd had affairs but never dated more than one man at a time.

My wife had left town for the weekend to visit her parents and had taken our son with her. I had the house to myself. I drank heavily the night they left; anything to stop fixating on Ken's request. I woke up drenched in sweat with a pool of cum puddling on my stomach. Groggily, I realized I had been dreaming about Maria having sex with two men while Ken watched. I must have had a wet dream and probably came when Ken came in my dream. I got up, made some coffee, and drank three cups wondering what the hell had just happened.

I hopped in the shower, scrubbed myself, used a depilatory, and shaved twice. Drying off, I powdered myself all over with my wife's sweet-smelling talcum. I went into our bedroom and put on my neck-to-thighs silicone prosthetic with the fake breasts and vagina. I put on my black satin waist cincher and dark smoke gray stockings with black seams. I realized I was dressing up the way I had been dressed when Mistress Nicola had taken me from behind in Las Vegas while she had me sucking a dildo.

I went back into the bathroom and did my makeup like that night. Not as good as Cassie, the woman who had done my makeup at the transformation service in Vegas, but close. I'd had lots and lots of practice doing my own makeup and had become very proficient. I walked back into the bedroom, put on my 23" black satin opera gloves and my black satin heels with the rhinestone accents. Then I got out all my rhinestone jewelry and put them on, choker necklace, choker bracelet, bangle bracelets, rings and dangle earrings. Looking at myself in the mirror, the memories of that night came flooding back.

Almost without thinking, I got out two of my dildos and laid down on the bed where I could watch myself in the mirror. I started by sucking one of the dildos and liberally dosing it with my saliva. Watching that thing disappear past my ruby painted lips was a turn on. I grabbed a tube of lubricant and squirted a small drop on my rosebud. I took the dildo I had been sucking and began to insert it into my ass. I watched it disappear and then turned it on. It vibrated and rotated at the same time; it was my favorite dildo!

I then began to suck another dildo while I fucked myself with the first one. In and out of my mouth and my ass, I was working those dildos furiously. Looking at myself in the mirror, it didn't take me long to cum, and I had a violent orgasm. Spent, I collapsed on the bed and looked at myself with a dildo up my ass and one still in my mouth. I realized I was going to grant Ken's request.

I grabbed my phone and called Ken. "Baby, it's Maria. I'm sitting here with a dildo up my ass and another one in my hand that I've been sucking. I had an incredible orgasm watching myself in the mirror. I've decided I want to do what you asked me to do."

"Are you sure, honey? I felt I had crossed a line which is why I never mentioned it again. Are you sure, Maria?"

"Yes baby, I'm sure. But...."

"But what honey?" he asked concerned.

"I just don't want to rush into this now that I've agreed. We've got to take our time and make sure the two guys we pick are the right guys. That we're both comfortable with them."

There was a long pause. Ken wasn't saying anything.

"Ken. You're too quiet. What aren't you telling me?"

"Um, Maria. I was hoping you'd agree to this. I've been 'interviewing' candidates already and I think I've found the perfect duo."

I giggled. "Ken! You're such a bad boy, you're incorrigible!"

"You mean you're not mad at me for doing this without your permission?"

"How could I be mad at you, sweetheart? Clearly this is a huge fantasy for you. I just hope I'm as comfortable with them as you seem to be."

"Oh Maria, you are so wonderful! I'll send you their online info so you can look them up to see if you think you might be comfortable with them too. If so, we can arrange to meet them in person to make sure."

"That sounds good, baby. Ken?"

"Yes lover?"

"Are you alone right now? Can you masturbate?"

"Yes, I'm home alone. What are you talking about?"

"I'm going to fuck and suck my dildos again while I'm on the phone with you. You're going to listen to me pleasuring myself and you're going to jerk off imagining what I'm doing."

"Maria, you are so fucking hot. Go ahead baby, I'm listening. I've already got my cock in my hand."

....

Ken and I were in agreement. Not only did Jimmy and Jerry seem like really nice guys, but they were brothers, identical twin brothers at that. I liked their online profiles. They were smart and funny. A little more than ten years younger than Ken and me, and while not as drop-dead gorgeous as Ken, they were really good-looking guys. They were 6' tall and weighed 180 lbs, had emerald green eyes and auburn hair so dark, you almost couldn't tell they were redheads. They were athletic and in good shape.

They agreed to meet us for drinks one night. They wanted to interview us as much as we wanted to interview them. The two of them had a threesome with a woman in the past but this was going to be w-a-y different. Neither one of them had ever been with a crossdresser before and neither one of them had ever had someone 'watch.' It was a big hurdle for them too and we knew it.

We met at a dance club. They had a DJ, but it wasn't loud, techno stuff. Older classics, soft rock, and R&B were played there and not ear shatteringly loud. I had decided to wear a figure flattering LBD that was cut just a few inches above the knee to show off my legs. I didn't want to go over the top and scare them, I wanted them to be comfortable with me, but I also wanted them to be attracted to me. I wore sheer black stockings and pumps with 3" heels. My makeup was underscored but I definitely wanted to look as feminine as possible for them. We ordered drinks and sat down.

They were absolutely identical; I couldn't even begin to tell them apart. They had been kind enough to wear different colored shirts. Jimmy was in green, and Jerry was wearing blue.

Jimmy said, "Before we go any further, Jerry and I want to let you know we are not making any decision tonight. We want the opportunity to talk about this by ourselves after this evening."

I gave him my best smile, chuckled and said, "Ken and I had already come to that decision as well, so it looks like we have that much in common."

Jerry smiled. "Maria, you even sound like a woman. If I hadn't known before we came in here, I would have bet anyone in the place you were a woman. Not only that, but you're definitely the best-looking woman in the place."

I blushed appreciatively. "A gentleman as well, I see. Common sense, good manners, you two young men have a lot going for you."

They were very curious about me. I had to tell them the tale of my evolution as a crossdresser. They knew Ken and I worked together, they were more than intrigued as I told them the story of how I had introduced Ken to Maria and seduced him.

A nice, slow R&B ballad came on. Jerry asked me if I'd like to dance. I told him I loved dancing, and he didn't have to ask me twice. He took me gently by the elbow and led me to the dance floor. It felt good being in his arms as we moved around the floor. Unlike Ken, Jerry was a very good dancer, and I was really enjoying myself. The song ended all too soon and we headed back to the table.

On the way, Jerry said, "If I didn't know any better, I'd swear you were a genetic girl. You're beautiful."

I giggled, kissed him on the cheek and replied, "Flattery just might get you where you want to go, Jerry."

We rejoined Ken and Jimmy and all of us had our drinks replenished. After some small talk, another slow song came on and this time Jimmy asked me to dance. "Of course," I said as I winked over his shoulder at Ken. Clearly this was part of the 'interview' process for these young men. They were separating us so they could talk to us one-on-one.

Jimmy was a little more aggressive on the dance floor. He pulled me close to him, really close. He had his hand in the middle of my back and my breasts were rubbing into his chest. He was grinding me with his crotch. Even while all this was happening, he was still a very smooth dancer. "I see you boys have had some dance lessons somewhere along the way."

Jimmy laughed. "Yes. When we were in middle school our mother insisted we take dance lessons in preparation for all the high school dances that would soon follow. We hated them at the time, but mother was right as usual."

"Do you like the way my breasts feel against your chest, Jimmy? I hope you like grinding your pelvis into mine as much as I like the way it feels."

Jimmy's eyes widened, then he blushed deeply. Maybe he wasn't expecting me to be so blunt. "I'm sorry, Maria. I didn't mean to be disrespectful by pulling you so close to me. I wanted to see if I could tell the difference."

"And?" I prompted him.

"I can't; I can't tell the difference. Even standing this close to you, hugging you against me tightly, you look, feel, and act like a gorgeous, mature woman."

"Please tell your mother that Maria said she raised two gentlemen who have incredibly good manners."

He blushed again and nodded to me accepting my compliment. He looked deep into my eyes and asked, "Maria, would it be OK if I kissed you? If not, I understand completely but I really just want to know and, and...."

I pulled his face towards mine and whispered, "I see you're the bad boy of the duo. I think I'm going to like you better. I want to suck your cock and swallow your cum first." Then I kissed him hard. At first, he was hesitant but quickly responded. I opened my mouth and thrust my tongue past his lips. He sucked on it expertly and I moaned with delight. The song was ending, and we stopped our passionate embrace. Just as he was starting to turn away, I ran my painted nails over his crotch. Now it was his turn to moan.

We walked back to the table, hand-in-hand. Ken's eyebrows were raised but he smiled at me and winked. The four of us began to talk about logistics. If this happened, where would it happen, how long would it happen. All the details. We seemed to be in agreement on most of them. We decided it was probably a good idea to leave. If anyone had any questions that came up later, they could always ask. And we left each other with these six words, "No hurries, no worries, no deadlines."

As we were walking to the parking lot, Ken was still talking with Jerry. Jimmy was deliberately slowing down, so I paced him. When Ken and Jerry had gotten far enough ahead, Jimmy looked at me and said, "Maria, I've already decided. I know I want to do this. I'm going to do everything in my power to talk Jerry into it too."

I stopped dead in my tracks and Jimmy stopped with me. "No!" I said this slowly and firmly. "You will not talk Jerry into anything. Jerry has to make up his own mind, not feel pressured into this by his twin brother. If we go ahead with this, the four people in that room must have made up their own minds and decided for themselves. That's the only way this will work and have a good ending."

Jimmy nodded. "I'm serious, Jimmy. If for one second, I feel any hesitation on Jerry's part, I will walk out of that room and not look back."

Jimmy nodded again. "Maria, you are as intelligent as you are beautiful. I promise I will not try to talk Jerry into anything. I'm even going to tell him about this conversation."

I slowly exhaled and said, "Thank you, Jimmy. Now let's catch up with Ken and Jerry."

On the drive home, I told Ken about my conversation with Jimmy. He was in complete agreement. The very next morning, Ken and I received an email from the boys. Not only did they want to go ahead with the threesome, but they were also excited about it. There was one major sticking point. They did not want to see Ken in the room. They had no interest in seeing another man masturbate. He couldn't be there.

I called Ken. "The boys are nice, honey, but we don't know them that well. I wouldn't be comfortable without you there. In fact, I wouldn't do this without you there. I'm going to email them back and tell them their request is a deal-breaker."

"Not so fast, baby. There's always a solution to every problem. We just need a little time to think about this. I'm going to email the boys and tell them we're still talking and haven't made up our minds yet."

True to his word, Ken began searching and found the perfect place. It was an upscale 'love hotel.' Specifically made for one-night stands or that couple just looking to step out of their comfort zone and spice up their love-life! It most definitely was not a sleazy dive.

We found the perfect room and asked Jimmy and Jerry to go look at it. They wrote us back and told us it was more than acceptable to them. Now the problem was finding a date that all four of us and the room would be available.

We finally found a Saturday, four weeks out. I was communicating with Jimmy and Jerry to see if they had any preferences on what I should wear for them. They had some general suggestions but had agreed to leave the final details up to me. They told me I had way more experience with women's clothing than they did and trusted my judgement.

Ken and I arrived at the hotel as soon as we were able to check-in. Jimmy and Jerry wouldn't be there for hours. I unpacked and hopped into the tub to soak in a luxuriating bubble bath. I had already done my nails in hot pink so as not to lose any time while they were drying. I douched three times as the tub was emptying. I'm not sure what it is about the number three, but it takes that many times for me to feel confident I am sweetly clean back there. I stepped out of the tub and powdered myself from head to toe with a perfumed body powder.

I wiggled into my neck-to-thighs silicone prosthetic with the fake breasts and vagina. I had chosen white as the color 'theme' for the evening. I wanted to look as virginal as possible for the boys. I had chosen a snow-white lace corselette with eight garter straps. The bra of the corselette had demi cups. They put my breasts on a lace 'shelf' but didn't cover any part of my nipples. I had decided not to wear any panties; the boys were going to know I meant pleasure as soon as they saw me.

I rolled the sheer white stockings up my legs. They had lace tops and I clipped two garter straps in front and two in the back for each leg. I had purchased white lace open-toe stilettos with 4" heels; it would make me just a little bit taller than Jimmy and Jerry, but they didn't seem bothered by my height at the club. I rolled the fingerless white lace opera gloves up my arms. I slipped on my faux-pearl jewelry, necklace, dangle earrings, bangle bracelets and rings. I was nearly ready. I finished off my look with a sheer white peignoir with feather trim and admired myself in the bathroom mirror. Maria was more than ready!

When I stepped into the bedroom, Ken gasped. "Holy shit!" he said. "I think I'm going to call the twins and tell them the night is off. I'm going to keep you to myself!"

"Like fuck you will." I knew, kind of, that Ken was kidding. "This was your idea big boy and now is no time to get cold feet. I'm going to fuck and suck those young studs and you're going to watch and jerk off."

Ken and I held hands while we looked at the room together. On one side of the bed, was a wall covered by floor to ceiling mirrors. Above it, the ceiling also had a mirror that was easily as big as the king-size bed. The genius of the bedroom was the closet in the corner that faced the bed. Looking at it from the room, all you saw was another full-size mirror. Inside the closet, was a very comfortable chair. From inside the closet, you could look out. From outside the closet, it was just a mirror. The mirror was one-way! Ken would be able to see us; Jimmy and Jerry wouldn't be able to see Ken!

Ken had placed a small cooler with his favorite beer and a few shooters of Irish whiskey in the closet. He also had a box of lubricated condoms. "Wow, honey, you look like you're getting ready to watch some porn." Ken grinned sheepishly but didn't have anything to say for once.

There was a gentle knock on the door. Ken kissed me (hard!) and then closed the door to the closet behind him. I checked my lipstick in the mirror, walked to the door, took a deep breath, and opened it.

I was hiding myself behind the door, the boys could only see my face as they were entering. When I closed the door and they got a good look at me, their expressions were priceless!

"O-h m-y G-o-d, Maria! I've never seen a sexier woman than you!" said Jerry.

Jimmy smiled smugly at his twin and said, "I hate to say I told you so, but I told you so!"

"Come in boys. Have a seat on the couch and let me pour you a drink while you make yourselves comfortable. Just leave some room for Maria between you on that couch." The twins had told us what they liked to drink. We had purchased enough of it to tide them over for the evening.

I poured their drinks for them s-l-o-w-l-y. I wanted them to take a long look at me in my virginal-white lingerie. Jimmy in particular couldn't take his eyes off me and kept touching his crotch. I strutted over to them with their drinks and sat down on the couch between them. The couch was opposite the bed but was also easily seen from the closet with the one-way mirror.

I snuggled in between them and gave them time to have a couple of sips. When they had settled in, I placed my hand on their legs near the knee and slowly began to run my nails up their thighs stopping just short of their crotches. Then I would run my nails back down their thighs to above the knees. I continued to tease them like this. I looked over at Jimmy and he leaned in to kiss me. I opened my lips and accepted his tongue, all the while continuing to massage both boys' thighs. I sucked on Jimmy's tongue for a while, almost forgetting Jerry was there. Clearly, I was way more turned on by Jimmy than Jerry, but I didn't want to forget why we were there.