My Best Friend the Tranny Ch. 03

As I drifted off to sleep last night, I wondered how I would feel when I woke up the next day. This was not just a homosexual affair. Stevie and I were dressed as women, having hot sex, taking pills to grow breasts and working for Sherrie Lynn and her ‘she male escort service.”

When I did wake up, I recalled how sweet it had been having Stevie’s cock in my mouth, and my asshole felt like a woman’s cunt must feel after a hot fucking. I looked over at the still sleeping Stevie. He looked beautiful as the sun shone in the window on his beautiful face. I wondered how he would feel about all of this. Although, his sister Jennifer said that she had caught him wearing her underwear, he was probably more prepared for all of this than I was.

I reached a hand over, stroking his face, “Wake up sleepy head,” I said in my fem voice.

He turned his head, eyes fluttering open, looking at me leaning over him. He reached his arm up, his hand cupping my head, “Hi gorgeous,” he smiled. I leaned down and kissed him.

“We had better get dressed and find out what, or who we are doing today,” Stevie giggled. We both giggled and started getting dressed.

Sherrie Lynn greeted us with smiles as we entered her office, “You girls seemed to be having so much fun yesterday that you forgot all about our shopping trip.”

“Oops,” we said, daintily covering our mouths with our hands.

“That’s all right,” she winked knowingly, “you are discovering fantastic things about yourselves, and your journey continues today.”

A strict looking woman came into the office. She was short, very stern looking. She wore no makeup and her hair was tightly wound into a bun.

“We are using a new drug,” she said matter of factly, “this grows your breasts quickly, and also gives you your womanly voice, and your skin a feminine sheen,” she smiled tightly, as though it was something she did not do often.

“You know ladies,” Sherry Lynne said after the short woman left, “you’ve made love to each other as fems, you need to have a real man make love to you.”

I nervously lit a cigarette. I thought of sucking Stevie’s cock while I smoked. I was really beginning to enjoy cigarettes.

“Don’t worry girls,” she giggled, “you spent last night exploring each other, learning how to suck each other’s cocks, how to fuck each other, that has prepared you each for a man, a masculine, virile kind of man. In the lobby, are two men. They are very handsome, and very hot for you. I want you to go in there, and act naturally. If you think you will have a problem with that, tell me now.” She looked at us, I looked at Stevie. I was not feeling nervous anymore, but excited. My nipples were tingling.

“Good, now go on, it is time for you to learn more about being women.”

Together, Stevie and I marched out of the office, and silently into the lobby.

The men waiting in the lobby looked to be in their early forties, old enough to be our fathers. They were very handsome men. They were wearing suits.

“Hi,” the tall one with the blonde hair smiled, “I’m Barry, this is Craig,” he said, pointing to the shorter one with the brown hair.

“Hello ladies,” Craig waved, very self assured.

“Hi guys,” I said, careful to keep my fem voice and mannerisms as I introduced Stevie and myself.

Stevie was staring at Craig, I could see the lust in his eyes. I was almost jealous as Craig responded to the stare, jumping up and coming over to my friend. He wrapped his arm around her waist and they went upstairs.

“I guess that leaves you and me,” Barry smiled assuredly.

I wanted to make him feel welcome, so I walked over to him, and sat on his lap.

We talked for a few minutes as he stroked my legs, then began moving his hand up my thigh. I was getting hard, my cock was straining against my nylons. Barry grabbed the head in his hands, rubbing me, “How does that feel honey?” he whispered hotly in my ear.

“That feels great Barry,” I leaned my head on his shoulder.

“You smell terrific,” he said, his face buried in my neck, he began kissing me.

This was totally new. With Stevie and I, we were giving each other hot sex. This was a man that I would have to give myself to. He was the man, I was the woman. He would be the aggressor, he would dominate me and I would respond to his needs. This was such a turn on for me.

We stood, he wrapped his arm around my waist. It was obvious we both had hard ons as he leaned down to kiss me. I wanted to respond eagerly, but I was the woman, so I waited for his lips to press mine. When they did, I welcomed them. His tongue pressed into my lips, I allowed it to come into my mouth, our tongues wrestled as we went up the steps.

We went into Stevie and my room. Craig laid on the bed as Stevie sucked his cock. I could not believe my eyes as Stevie worked his hand up and down Craig’s shaft, sucking his cock, then deep throating him. I led Barry over to the other bed. He stood over me, smiling down at me. I reached up to touch his face.

He leaned down, once again in a romantic lip lock. I was so hard, and my sensitive asshole yearned to be fucked by this hot looking man. I sank to my knees, undoing his belt, eagerly reaching inside and pulling out his large penis. It was larger than mine anyway. I locked my mouth around the bulging head, sucking on it, working my tongue around the head, then licking up and down the shaft, taking time to suck each of his balls into my mouth, sucking on them as he moaned his approval.

He began undressing as I continued sucking on him. Then, we were in my bed, he kissed my chest, sucking on my nipples, using his tongue to circle each one, kissing his way down my hairless chest, down to my hairless triangle. Then, his mouth was on my cock, sucking it, licking it. I tenderly held his head in my hands as he sucked my hard cock.

“Barry, I’m about to cum,” I sighed.

He stopped immediately, my cock plopped out of his mouth and he threw my legs up in the air. He shoved his cock in my mouth, I slicked it up with my spit. Again, he pulled it out of my mouth, immediately pressing the tip into my asshole, I relaxed as he pressed into me, pushing inside, slowly, but in one continuous motion. The feeling was out of this world. He began to thrust back and forth, slowly at first, then faster. He was finally going at a fast, steady rhythm. I looked over, his pal Craig stood in front of me, his hard cock staring me in the face, I opened my mouth. I was sucking him as Barry fucked me, Stevie came over and sucked my nipples, it was fantastic.

“I’m cuming honey,” Barry gasped, firing a tremendous load into my asshole, the warm spurt felt so good while Stevie wrapped her mouth around my cock. He sucked me as Barry continued to thrust into me and I continued sucking Craig.

Barry pulled out, the cum followed, flowing out of my ass as Craig began moaning and I felt his cock spasm in my mouth, I eagerly sucked his cock as he was cuming, as I surprised myself, suddenly cuming in Stevie’s hot mouth.

We all collapsed on the bed. I gave Stevie a cigarette and had one myself. We played some more on the bed before the men said their good byes.

As I sat there, smoking with Stevie, I realized that this was not just something we would do and forget about, and get on with someone else’s idea of a normal life. We were enjoying sucking cock, fucking and getting fucked in the ass.

This was before we began the medicine that would make us even more feminine. In the space of two days, I had become someone else completely. Not just the women’s clothes and the girlish name, but I enjoyed it when Barry took me, I enjoyed being under his control. I liked being held by a man, being made love to by a man while wearing my feminine clothes and makeup.

I could never go back to the way I was only two days ago. I was someone totally different. I would become a she male. I would anxiously await the changes that were about to make me even more feminine.