tagTranssexuals & CrossdressersThat's What Friends Are For

That's What Friends Are For

bytsipper©

I had been at my job for about a month. The job had forced me to move to a new state. The only people I had met were my fellow workers. I had ventured into the normal places that a single male would go to meet people...clubs, but had met no one.

One day Bob, who had the cubbyhole next to mine, asked if I wanted to come over for dinner with him and his wife Dee. I had told him of my loneliness so he took it upon himself to befriend me.

I arrived for dinner around 7:30. The conversation was basic small talk, getting to know everyone. And yes...sex was part of it.

After dinner we headed to the den. It was Dee that suggested we play "Quarter Bounce". Now I had been a participant in this contest before but I had always known my fellow competitors. I was headed into uncharted territory.

I began to get nervous. Being 5-9 and 135 my alcohol tolerance is very low. I was certain I was in trouble. Jerry was 6-5 and 250 and a solid 250. As for Dee, I had never been able to drink a woman under the table. Something was up.

I was able to keep up only because of my accuracy. Now I had always been turned on by seeing a woman intoxicated. Every time I bounced a quarter in I chose Dee to down her shot. But Dee and Bob ganged up on me. And soon my accuracy began to suffer but not theirs.

After a while I had to excuse myself to the bathroom. When I came back they decided to end the game. According to their rules, the game is over at the first restroom break. Good thing because I was wasted by this time. So we adjourned to the couch and continued our dinner conversation.

After some pleasant and humorous chatting, Dee asked me what the kinkiest thing I had ever done was. I told her about an experience in college where I had put on panties on a dare. Dee reacted to this by moving closer to me.

"Funny you should mention that," Dee said. "I have always wanted to dress up a man like a woman, but Bob is not a willing subject. Would you do it?"

I was kind of shocked. I had just met them as a couple. This was rather forward, but I remembered how those panties felt that night long ago.

"Not really," I said.

Now Dee had slid right next to me and began to rub my thigh. I was getting hard and she made it a point to bump against my manhood. Resistance was never a strong point of mine and Dee was very persistent.

I began to worry that Bob would get pissed that Dee was working on me. I looked over at him and he had a devilish smirk on his face. I was in BIG trouble.

Dee kept the conversation going about various subjects but kept caressing my thigh. Occasionally she would ask if I was ready and got the same answer. Finally Bob chimed in.

"Dude, she won't quit. Trust me, I know."

Dee was looking into my eyes. She leaned over and began kissing me. What was I supposed to do? I tried to pull back but she reached into my pants and began stroking me. That was it.

"Okay, you win. I'll do it, but Bob has to stay in the living room."

With that Dee grabbed my hand and helped me back to the bedroom. I just stood in the middle of the room, staggering from my drunken state.

"Let's start by removing these," Dee said. With that I was barefoot.

"Now let's get started," she said. She then unzipped my jeans and very slowly pulled them down to the floor. She noticed that there was a wet spot on my briefs.

"We better be careful. Don't want an accident to happen." And just as slowly she pulled my briefs off. My cock jumped to attention.

"Okay, let's see what I have here." She looked around in her dresser drawer and pulled out a pair of blue panties. "These will do just fine."

She knelt down and lifted one of my legs and placed it in the hole. Then the other leg. I couldn't believe I was actually doing this.

She slowly pulled the panties up and over my ass until I was completely covered again. I admitted to myself they felt good.

"How do they feel?"

"Pretty sexy," I said.

Now she had in her hand a pair of panty hose. As a teenager I once wanted to try on a pair of my mom's hose, but was too scared.

"She is really going to do this," I thought to myself. "And I am going to let her."

She sat me on the bed, lifted my legs up, placed my feet into the stocking part and rolled them up.

"This is making me wet," she said. "We may not get you completely dressed."

She headed into the closet while I was admiring myself in the mirror. My legs looked good. My ass was round and bulbous, ghetto booty.

Dee emerged from the closet with a white slip, a black lace bra, a blue dress and something in a box.

My heart was racing. I was giddy with anticipation.

"Let's remove this," she said. And off came my shirt. "Now slip your arms in." Before I knew it, she was latching up the bra and putting falsies in the cups.

"What next?" I asked. I could not believe I wanted her to hurry.

"Lift your arms up," Dee said. I obliged as she slid the slip down over my head and down my body. I was in heaven. The silk felt so good on my body. Then came the dress.

"I want to see," I squealed. "Let me look."

"Hold on, one more thing," she said. She opened up the box and pulled out a wig, slipped it on my head and adjusted it. "Perfect."

I looked into the mirror and couldn't believe what I saw. I was seeing a totally different person looking back at me.

I was admiring myself in the mirror when Bob came into the room. He walked up behind me.

"Not bad," he said. "Not bad at all."

Then he did something unexpected. He began gently rubbing my ass. "Very nice," he said.

I began to get scared. What did he have in mind?

I soon found out. He reached around my waist, lifted up the dress and skirt, reached into the panties and began stroking me.

I was in a fog for about a second. He was so gentle.

This was a man doing this to me. Hold the phone...A MAN.

I tried to struggle to get away but I was no match for him. He wrapped me in a full nelson and then let Dee get in front of me. She got on her knees and slid my cock down her throat.

She was good. I soon relaxed. I just closed my eyes and let Bob hold me up while Dee did her magic.

I had never been so hard in my life. She was all over my cock and had me in heaven. I felt like a totally different person.

Then I felt Bob pull down the garments covering my ass. His hand began working its way into my crack and his finger was wet and cold. There was some sort of liquid on it. Then I realized what was coming next.

He pressed his finger, covered with a lubricant, into my hole. Nice and slowly he pushed it in. I was familiar with this as a former girlfriend used to do this to me and I loved it.

I shoved myself into him. His finger went in up to the first knuckle. He began moving it around getting me nice and slippery. My hole slowly adjusted to the intrusion. I was now moaning in excitement.

Just then Dee took her mouth off of me and climbed onto the bed. I wasn't sure what was next, but I soon found out. Bob whirled me around and threw me face down onto the bed. Dee grabbed my arms and held them straight out. Bob lifted up the dress and skirt, pulled down the panties and hose and spread my cheeks.

The head of his cock was at the entrance. Slowly he pushed it through. I howled in pain, but it felt good. He stopped, allowing me to adjust to the plug in my butt. Little by little he pushed in further until I felt his thighs pressed against mine.

Dee lifted my chin. "How you doing lady? Feel good?"

All I could do was moan and lower my face onto the mattress.

I was being slammed by a man, something I would have never dreamed of happening. Bob began to slowly draw himself in and out. I soon found myself thrusting into him.

Bob began to pound away. "First timer," he said. "Nice and tight. I love it, a virgin."

I was gasping for breath in excitement. Every thrust sent me further into delirium.

I knew Bob was strong, but I did not know how strong until he wrapped his arms around my waist and lifted me off the bed. He held me off the ground and began pounding away.

I was folded in half. I was flopping around on his cock like a rag doll. My cock was hard enough to cut diamonds. It was so rigid it would not flinch an inch. I soon began to feel my toes tingle.

Dee noticed my sac stirring. "You're ready to cum," she said. "Let it loose, spray it."

And with that I straightened up and exploded. I thought I had shot my cock completely off my groin. My cum shot halfway across the room. I felt like I was going to fill Lake Superior.

The last of the spurts subsided and Bob laid me down on the bed and pulled out. I was spent, but they were not through.

While I was being ravaged, Dee had slipped into a strap-on.

"My turn," she said. She lifted up my hips and helped herself inside my ass.

"Next time, don't resist me," she said. "You know you like it."

I was in heaven again. Her dildo was just the right size. She was pounding away and I loved it. And once again I was hard as granite.

Meanwhile Bob had returned from the restroom after bathing his cock. Dee pulled my arms behind me and balanced me on my knees. Bob inched closer and placed his cock on my lips.

"Let's see what kind of woman you really are," he said. Then he shoved his cock down my throat.

There I was being pounded at both ends. I had always wondered what a woman thinks with a cock in each end. Now I knew.

Bob and Dee had good rhythm. Every time Bob shoved himself in, Dee did the same. My cock was ready to explode again and so was Bob's.

I tried to get my mouth off of him but I was held prisoner, my arms by Dee and my head by Bob. Bob's cock began to swell. He was about to cum and I could not get away.

"Ever tasted a man's cum," Bob said. He reached down and pinched my nose close right at the time he exploded into my mouth.

He filled my mouth and throat with his nectar. I could not get it out of my mouth. I had to swallow. I found myself lovingly sucking his cock dry. Some oozed out of the corners of my mouth but I managed to drink most of it. Not as salty as mine; I had tasted myself before. Dee let loose of my arms and I wrapped them around Bob. I wanted all his juice. I licked his cock all over. I did not want it to go. I sucked and licked him gently back to an erection. All the time Dee was working my ass hard.

"You want some more don't you," Bob said. "Be careful what you wish for." Bob started to get hard again. I began to fondle his balls and Bob moaned. I now had Bob in ecstasy. I wanted to see how far he would let me go. I slid a finger into his crack. He grabbed my hand and shoved the finger in. He must have anticipated this because he was all slippery inside. I worked him over until I felt his cock swell again. He growled, pulled my head into him and blasted his juice into my throat. Once Bob had emptied himself, Dee pulled me back onto her.

"Ride me," she said. I was more than happy to oblige. I had done this before with girlfriends. I was bouncing on her like a trampoline. Bob then leaned in and began licking my cock. I wanted him all over my cock, but I was in a very high state of arousal. With the first touch of his lips I blasted into his face.

"Whoa, wasn't ready for that," he said. He clamped down on my cock and sucked out my juice. It was so sensitive and felt so good. A man knows what a man wants. Before he could regroup I was finished.

With that Dee let go of me and I fell over. Not an ounce of energy left. Dee and Bob began caressing me, rubbing my forehead, running their hands all over my body.

"You were very good," said Bob. "We'll make sure nothing happens to you."

Within minutes I was asleep, or passed out. When I awoke I was still in the dress, slip, bra and wig. I was sandwiched between the two of them, Dee spooning me. The panties and hose were in a pile on the floor. I was itching around my crotch and reached down to scratch. My cock was hard but something was different. I was now clean shaven. Dee must have notice my stirring because she reached around and began stroking me.

"Like that?" she said. "We wanted to surprise you with a little something."

As if what happened the night before wasn't surprise enough.

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bytsipper© 6 comments/ 44554 views/ 8 favorites

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