My Cross-Dressing Secretary

"I suddenly had an idea," Alan said. "If I'll fuck Inez, do you think she'd be willing to lend me her apartment for a private get-together?"

"There's a chance she would, but I wouldn't do that. Inez is a great gossipmonger. She'll probably lay an ambush outside her apartment just to know who's coming. If anything, then maybe Susan."

He was silent and considered my words. "Are you in favor of the idea?" he asked.

"The question is whether you're interested in fucking Susan. She's at least 50 years old."

"I don't have a problem. I don't have a girlfriend, and even though my penis is small, I know how to use it."

"Okay," I replied.

*****

Ever since we started fucking, Alan had been careful not to sit next to me in the hot tub, and I congratulated him in my heart for it. He made sure to sit directly across from me, but in recent days, he had deviated from his habit and, instead, sat down next to Susan. A few days later, he couldn't hold back and sent me a small smile of triumph. The little bastard managed to put Susan in bed.

To be honest, I had no doubt that he would succeed. All of them were widows or divorced women living alone. Swimming flooded their bodies with adrenaline that must have raised their testosterone levels, and the only outlet they had was their fingers or, if someone was a little more elaborate, a vibrator. My performance at the pool and then Alan's joining, certainly didn't improve their situation. They were crying out for cocks.

My heart ached a little for the cynical exploitation we were doing of Susan, and I made a note to myself that if anyone will get a fuck from me, it would be Susan.

I got into the showers and dragged a plastic chair behind me. Since he rode me, we've already expanded the spectrum of our poses. He got into the shower, saw the chair and smiled expectantly. I stood him in front of the chair seat, leaned his body on the backrest, and lifted his leg on the seat. He rocked his butt in anticipation of my cock.

As usual, I applied some shampoo to my shaft and... I inserted it all at once. He arched his back in surprise and immediately heaved a heavy sigh. I must have hurt his prostate. He pushed his butt out and fucked me backwards. While fucking he asked, "Can you evacuate a few hours before noon in the next few days?"

"How was it with Susan?" I asked.

"Explosion. She's really good in bed. Just so you know."

"Maybe on Friday," I replied.

"Not good," he said. "Susan teaches Monday through Thursday before noon and it's our time."

In retrospect, I remembered that Susan was a First Grade Teacher. In fact, she was Kelly's teacher, my daughter, and she was a great teacher.

"I'll give you an answer tomorrow. What did you tell her?"

"That I'm having an affair with a married woman."

"And what did she say about that?" I asked.

"She wasn't criticizing. I think she knows firsthand what sexual need is."

Wise child, have I already said?

The thought that I was going to fuck him long on a bed, like a fuck should be, completely warmed me up. As usual, I massaged his cock while fucking him. Only this time I fucked him hard. He let out moan after moan and seemed to barely hold back from screaming in pleasure.

Again, he cummed before me and squirted his sperm on the chair.

"God, Mr. Ryan, the orgasms you give me are better than fucking a woman."

"Wait," I said. "I didn't cum yet."

I continued to fuck him hard and he cummed again, squeezing his wonderful asses on my cock. I began to feel the orgasm climbing up the road from my testicles to my dick.

"A little more," I said. "I'm already cumming. Oh, my sweet God, it comes strong."

"Yes, Mr. Ryan, fill me in. I think I'm going to cum third time."

I cummed and he cummed too. Once again.

*****

A week later, we met at Susan's home.

That morning, Alan didn't show up at the pool. I knew about it in advance, and I think Susan knew as well. But Alan's non-appearance revealed an unknown fan of his -- an auntie of about 55 years old, relatively short, thin, shapely and muscular, named Elsa. She was really thrilled by Alan's absence and tried to get his phone number in every way possible "to get an interest in his well-being."

I got to Susan's house at nine o'clock in the morning. A beautiful blonde young woman opened the door for me. I assumed it was Susan's daughter, and that we had a misunderstanding here. I apologized politely and was about to leave, when the blonde took my hand and pulled me into the apartment.

My pulse started to quicken, but at that moment I recognized him. It was Alan and he was wearing a tight dress that reached mid-thigh and wore shoes with a wide but high heel. He had breasts, but I guess he just pushed cotton wool, or some other material, into his bra. His hair was arranged so that it all spilled to one side, and he was made up in a very delicate and very attractive way, with eyeshadow, blush and bright red lipstick.

He seemed to be a young girl in the full sense of the word, and not just any girl, but a beautiful and attractive girl. Just by looking at him I had hard-on.

I stroked his face and said, "God, you are so beautiful."

He smiled mischievously and asked, "So I can be your girlfriend?"

"Damn, yes."

I grabbed him, pinned him to the wall and kissed him with animal force. My hand moved to the bare part of his thigh, and I caressed his soft skin, raising his skirt up to his butt, giving it a hard crush. I pressed my body against his, and my erection pressed against his stomach.

Then he had a glitch. Through his tight dress raised a bulge pressed against my hard erection. His dick hardened, too. I picked him up and carried him into the bedroom.

For the occasion, sweet Susan changed all the bedding and even bothered to light a scented candle. Two towels were neatly folded on the dresser ready for our use. She is a good soul, Susan. I threw him onto the bed and stretched out on top of him, kissing and licking his neck. My hands groped every part of his body and even crushed his breasts, until I remembered that it wasn't breasts, but some filling.

He reached for my pants and stroked my erection. I stroked his thighs and lifted the hem of his dress up to his waist. He pushed me over him and unbuckled my belt, and then my pants. He pulled my rod out and wrapped it in his sensual red mouth.

It was the first time I got a blowjob from him, and it was heavenly. He licked my shaft, then put the tip of it in his mouth and sucked. His tongue ran through his mouth, tickling the slit under the head of its crown. I grabbed his head and pulled him hard on my boner. He managed to insert half of my cock into his mouth before his gag reflex overtook him, then he lifted his head, took a deep breath and gave me a seductive smile as his hand rubbed my rod up and down.

I got out of bed and quickly undressed. He was about to undress too, but I stopped him.

"I want to undress you," I said.

When I was naked, I slowly pulled his dress off, enjoying seeing his smooth body exposed to me. I leaned over to lick his soft skin from his neck, through his chest and stomach to his loins. I caressed his thighs and crushed his butt. I couldn't take a break from him, and my tongue and hands ran across his body from place to place without any plan or order whatsoever.

I unraveled his bra and licked his nipples. Unlike me, his nipples were sensitive, and he began to squirm, hugging my head and pressing it against his chest. Then... I rolled up his underwear and took his dick into my mouth.

It was the first time in my life that I sucked a cock. Since he had a small one, it didn't feel very strange. At most, as a too big bite of carrot, except carrots don't swell in your mouth or tremble. And what made all the difference was the thought that it was a dick.

I lifted my head from his, smiled and said, "I'll suck your, but woe betide you if you cum in my mouth."

He smiled back and said, "I promise, provided you promise to cum in mine."

I caressed him and he caressed me, I licked him and he me, we kissed a few times and finally I turned him over on his stomach, filled his back with little kisses and went down to his beautiful asshole. I licked his gorgeous rose and tried to stick my tongue into it. I didn't quite succeed, but even so he let out a loud sigh.

He sucked my cock again, then lay down on his back, lifted his legs and said, "I want you to fuck me like a man fucks a woman."

I positioned myself between his legs and aimed my dick at his anus. I squeezed and his anus readily complied. I inserted my cock into his trained hole and fucked him. He wrapped his legs on my back, pulling me into him and tightening his grip on my rod by contracting his butt.

He removed his legs from my back and spread them to the sides. I leaned over and kissed him. He wanted me to fuck him like a man fucks a woman and that's what I tried to do. I fucked him in long motions, pulling my cock almost out and then forcefully inserting it inside. This time he was literally screaming with pleasure.

I lifted my mouth from his and just looked at his beautiful makeuped face.

"Ugh," I whispered, "you're so beautiful. I want to fuck you for hours without cumming."

"Let's try to do it," he whispered back.

A few minutes later I started to feel like I was close to orgasm, but I didn't want to cum, so I stopped and rose above him. I placed his legs on my shoulders, staying in that position without moving, just massaging his prick.

"It's not fair, my love," he whispered. "I can cum like this."

"So cum," I replied. "It won't stop me from continuing to fuck you."

"I'll get us both dirty," he said.

"So get dirty, but I don't lick." he burst out laughing, letting me to stroke his dick.

When I felt the need to cum, I leaned over him again, kissed him and went back to fucking him as before. He lifted his loins off the bed and rocked his butt, giving more stimulation to my very aroused cock. Then he let out a long scream and squirted a long jet of sperm that reached his face. He collected his semen with his finger and licked it.

I held him with his strong, pleasant thighs and fucked him hard. This time, as the orgasm built inside me, I knew I couldn't stop it. Just before it arrived, he pulled me to him and I lay on top of him, crushing his body with mine. He was strong enough to carry me. Then my whole body shook, and I sent jet after jet of hot, sticky glue into his intestines.

I lay on top of him, trying to catch my breath. It was the strongest orgasm I've ever had, and my pulse was raging. He stroked my head and kissed my face, almost lovingly. When I calmed down, he pushed me away and laid me on my back. This time he lay on top of me, caressing my body and kissing every bit of it. Slowly, he descended towards my groin. He grabbed my balls and licked them and sucked them, one by one. Finally, he put my meat in his mouth and sucked it hard.

The intense orgasm I had left me exhausted, and I couldn't believe he would be able to get my erection up again so soon. But he succeeded. He sucked all the blood out of my body and concentrated it in this lump of flesh called a cock, then he licked it from end to end and sucked again. I felt tingling in my balls and was afraid to cum even before the next fuck will start.

But he wouldn't let me. He stopped and lifted himself up to me and went back to kissing me. Finally, he sat down on my thighs, lifted up slightly and inserted my cock into his ass sitting down. He didn't try to fuck me. He just sat on my cock and masturbated.

I stroked his thighs and stared at his pretty face, then asked, "Say, who made you up like that?"

He smiled and said, "My mother."

I missed a beat. "Does she know about us?"

"She knows I have someone, but she doesn't know who."

"And she doesn't have a problem with that?"

"My mom? No problem. She's the most open person I know."

"And your father?" I asked.

"If my dad knew I was getting a cock in my ass, he would have burned my hole."

"Wow," I said, "what a gap."

"Yes. My dad is just square, maybe that's why my mom cheat on him."

I burst out laughing. "Don't tell me she's telling you."

"Not really, but not trying to hide as well. I think you'll like her. Do you want me to introduce you?"

This time my laughter was really rolling. "And then what?" I asked. "We'll have an orgy and I'll fuck you both?"

"Why not? Although I'd rather not share you when I'm in bed with you."

"Just so you know," I said, "I've never cheated on my wife, except with you."

Then a disturbing thought occurred to me. "Tell me one more thing. You and your mother?... Have you ever been together?"

"Not that I have a problem with that. But no. Never."

And with that he wiggled his butt on my cock. I took a deep breath and indulged in the waves of pleasure my dick sent all over my body. This kid's ass was maybe the best sexually thing that ever happened to me.

That morning I cummed two more times, once in his ass and once in his mouth. He, of course, swallowed every drop that came out of me and licked his lips.

*****

I don't know if Susan told the girls about her relations with Alan, or if they felt alone in a new sexual tension, but one morning as we showered, Inez and Elsa burst into the men's shower. They were dressed in their swimsuits -- both with one-piece swimsuits, but in Inez's case with a large cleavage that showed off a good portion of her heavy breasts.

"What are you doing here?" I asked in horror, aware that if they had come in just a few minutes earlier they would have seen me fucking Alan. "This is where the men's showers are."

They didn't care. Inez charged at me while Elsa attacked Alan. "Sorry," Elsa said, "we can't stand it anymore."

Inez pushed me into the partition between the showers, knelt down and put my cock into her mouth. I turned my head and saw Elsa pressing Alan against the wall with his dick in her mouth. Inez sucked me like there was no tomorrow. I had already gotten a blowjob from her, but this time there was much more passion in this. My rod is quite big and very thick, and she took most of it into her mouth. Last time she barely got half of it into her mouth.

Despite the orgasm I had in Alan's ass, my cock swelled very quickly and reached an erection in no time. Inez tried again and again to take it all in her mouth, so far without success. But she did a very good job sucking and licking it. She pulled my both hands to her chest, inserting them through her bathing suit. I cupped her heavy, soft breasts and crushed them.

After both hands were placed where she wanted, she moved one hand to my balls, massaging them gently, while put her other one between her legs. She pulled aside the bottom of her swimsuit and massaged her clit in quick circular motions. All this time she continued to suck me hard and tried to swallow as much of it as possible.

My cock was very hard, but the orgasm in Alan's ass was intense and it didn't look like I was going to cum anytime soon. That didn't deter Inez. She continued to work on my cock and her pussy at the same time, and at one point she buried her head forcefully in my crotch with her whole body trembling with intensity. She stayed like that for a few moments, not releasing my cock from her mouth and then went back to sucking it.

I looked at Alan. Elsa took his entire little dick in her mouth and galloped back and forth on it. Alan had no reservations about the subject. His hands gripped Elsa's head, pressing it close to him and indulged in the pleasure of sucking. He noticed I was looking at him, lifted his head, saw me, and winked at me with a smile.

Even though I made her have a hard time, Inez didn't despair. She wanted me to cum in her throat and worked intensively on my prick. I pulled my hands from her breasts and stroked her head. All in all, she is a good woman who needs confirmation of her femininity. She pounded her head into my crotch again, this time almost all of my cock was inside her mouth, and cummed again. Judging by the seizures that attacked her, I would say that this time she cummed more forcefully.

She pulled her head away from my cock, looked up at my face and asked, "Is there any way you're fucking me? I don't have the energy to keep sucking anymore."

"You're an attractive woman, Inez. I'd love to fuck you, but you know I'm married."

Alan had no problem with fucking. He turned Elsa with her back to him, pulled her bathing suit off in one swift motion, bent her against the wall and penetrated her. Inez looked at them enviously. I lifted Inez off the floor and kissed her. I pressed her against my body and whispered, "Wait a bit. If Elsa will cum before him, maybe Alan will fuck you too."

She put her head on my shoulder for a few seconds and then backed off. I finished my shower and went home.

*****

That morning I received an invitation to a three-day, full-board, actuarial conference at a country guesthouse near Mountain Lake. I called to confirm arrival and the secretary on the other end informed me that since I was one of the first ten to confirm arrival, I was entitled to an escort. Plus one. In an instant, I had an erection. I confirmed I would arrive with an escort.

The thought of taking Alan with me, dressed as a woman, as my secretary, and for three days, took me out of focus. I smeared the day and went home earlier than usual.

*****

A few days later we met again at Susan's. He again greeted me dressed as a woman and made up. I hugged him and made love to him for five minutes standing at the entrance to the apartment. Finally, I informed him that in preparation for the trip to Mountain Lake, we had to change his name to feminine.

"Helen," Alan interrupted, "and I'd also love it if you started calling me that in our sexual encounters."

"Okay, sweet Helen. How about giving daddy a good suck?"

He got down on his knees, opened my pants and asked, "Daddy? Are you talking to me or Billy?"

"Of course to you, sweet Helen. Billy is my son."

"Let go. So what if he's your son, I'm sure you were turned on his ass."

I thought about it for a moment and replied, "His ass is beautiful, but I wasn't turn on him."

My cock was already in his mouth, so he couldn't reply.

I stood at the entrance to Susan's apartment with my prick in this beautiful boy's mouth, stroking his head. I noticed that in the months since we met, he hadn't cut his hair, and it had already reached his shoulders. I gathered his hair in my hand into a small ponytail. He looked up at me with a smile in his eyes.

As always, he sucked me as best as possible, getting almost all of my rod in his mouth, sucking it hard and licking the flesh that inside his mouth. Every now and then he would go up and down on my cock, while sucking, causing my blood to gather at the glans of my cock. He pulled my pants down and massaged my balls. Then he reached between my legs and massaged my asshole. I leaned against the wall, certain that if it wasn't for the wall I would have collapsed on the spot.

My legs started shaking, which has never happened before, and my cock seemed about to break away from my body. With his other hand he stroked my thighs and climbed up to my butt, doing to me what I had always done to him. He kneaded one cheek, pulling it aside and opening easy access to his other hand to my asshole, which was already contracting and loosening alternately.

I felt the orgasm build up in my testicles and seek to erupt. But he pressed his thumb on my urethra pipe, inhibiting the orgasm from erupting.

I was in the clouds.

He pushed one finger into my anus while his thumb pressing the bottom of my pelvis. The accumulation of liquids in my balls was already unbearable, very close to pain. His hand caressing my ass crushed it and slid from it to my thigh and then back to my ass. And his mouth... His mouth caused waves of crazy vibrations all along my shaft. I had to cum and fast.