tagTranssexuals & CrossdressersPleasure from Pleasure

Pleasure from Pleasure

bydarkestnight©

Chapter 1: An Interesting Twist

That lust in his eyes turned me on spiritually. Hell with the physical stuff, that was just friction and heat, a hormonal drive that drove the body to instinct and pleasure. This was something else, an emotion that made my whole body tingle and my mind whirl at the speed of light. All this from a simple look.

We were new to one another and he had just learned my secret. To my great relief and joy, he wasn't put off by it at all. Quite the contrary, his curiosity drove him toward acts of exploration that I was certain he had never considered before. His beautiful brown eyes drank me in, consuming me with the same appetite that I felt, the same starvation.

His dark hair was stylishly messy, his strong features thin, well proportioned. I admired the curve of his lips and imagined crushing mine against them. He was dressed in a black suit jacket, black button down shirt and black slacks. The Johnny Cash look suited him, especially with his pale skin and two days of facial hair decorating his cheeks and chin.

We made a good pair in our fashion that evening. I wore a little black dress with a keyhole in the chest, showing off my cleavage, made more prominent by a push up bra. My stockings were black, peeking out from under my skirt and showing off to the world that I used a garter belt. Black, five inch heels finished off the affair, buckling around my ankles.

I wore my red hair long but tied back so that the front would frame my face and the tail lifted the rest from my slender, pale neck. My makeup was specifically designed to enhance the green of my eyes, the red of my lips making them just a little bigger. Jewelry was white gold, pearls hanging from my ears and a matching pendant at my throat.

It had taken me years to get to that point, a lot of hardship and misery but after everything I had been through, I could pass for an attractive woman--not just a sad drag queen out for a thrill by wearing panties and a dress. I had surgery to enhance my breasts, a procedure to get rid of facial hair, hormone therapy from a good doctor and enough voice lessons that there wasn't a shred of masculinity in my tone.

There was one thing that remained from my former life as a man and that was my genitals. In fact, staring at this man across from me had it stirring in my satin panties, even as it was carefully tucked to avoid an embarrassing bulge. I crossed my legs, smooth and clean shaven, to help suppress an uncomfortable erection.

I could see the wheels turning in his mind as he considered what to say. Our conversation had turned to something naughty and I decided it was time to explain myself. The conversation was much better in a club at a table across from one another than in the bedroom with that false innocent look to him saying 'I thought you knew'.

Nothing should be left to chance and much as I wanted him, I needed him to be okay with who I was.

When he didn't say anything for five minutes, I decided to prompt him.

"You can ask me anything...I won't be offended."

"Are you gay?" The first question that a lot of people asked and I was disappointed. half of me expected it though so I just took a deep breath and shook my head.

"No, that would assume that I was a man. I might have a penis but I'm not a man. I haven't felt comfortable in my body until very recently when I could come out in public and not feel like people were staring. I mean, look at me. If I was gay, wouldn't I be after a woman?"

"But you have a penis."

"Yes, but I also have these." I grabbed my breasts. "And maybe one day, I'll get rid of that penis...take the final plunge but for now, I'm happy with who I am. I don't think I need anymore change to be me."

"I'm surprised how hot you are...I mean, I've seen she males before and they weren't nearly so hot."

"You might've seen more than you've ever realized. Some of us are lucky and were kind of effeminate to begin with. It didn't take a whole lot for me to get this way and once I started the therapy and got some surgery out of the way, I was passable."

"Do you always dress like a woman?"

"I probably dress more like a woman than your last six girlfriends combined," I replied. "Before I could get the final surgery, I'd have to be out and about for a while, really living as a woman. I prefer taking it to the next level, suffering a little for fashion. I only wear pants when I have to do some work outside and never leave the house without full on makeup. It's just how I am about it."

"You dress like this every day?"

I smiled. "No, I try to keep it appropriate. I don't go grocery shopping in club clothes. But I do throw on a sundress and at least a nice wedge shoe. Platforms or heels are a guarantee though."

"Jesus, that's really hot."

"I'm glad you like it...Honestly, I'd dress in whatever you wanted if it turned you on. Seriously, I'm in a place where I take being feminine to an extreme. I like feeling a man get excited because of me...of pleasuring him. I'm even happy to let my excitement come later. It's fulfilling...even the way you're looking at me right now. Absolutely thrilling."

He sat quietly for a few moments. "Thinking of questions...it's hard. I don't want to...you know...be offensive."

"I would've thought my candor would make it clear that I'm not easy to offend but if you'd like, I'll tell you a few things that might make you blush."

Now he smiled. "Go for it."

"Unlike your average girl, I would encourage my man to watch porn. I'd even happily suck him off while he watched it, let him reenact some of his favorite scenes." His breath caught in his throat. "Yeah, if you're wondering about facials, sure...cum on my face. Would it thrill you to see me on my knees looking up at you as you covered my lips? Got it in my hair? I'm in it for your pleasure and if that's what you want..."

"Does that do anything for you?"

"I wouldn't do it if it didn't."

"You're too good to be true."

"Except that I've got a cock."

"Maybe that's why you're so intriguing."

"I seem to be winning you over."

"I'm an open minded sort."

I moved over to his bench and drew closer. "Are you suggesting that you'd like to give us a go? See if you enjoy having an extreme woman? I'd wear my stockings to bed...blow you in the night. Tell me what your pleasure is."

"Do you get offended by dirty talk?"

I laughed. "I just offered to let you give me a facial. Do you think I'd flinch at the word fuck?"

"I really want you...desperately. I want your lips on my cock, you looking up into my eyes as I take you deep."

"Yes." I whispered, my eyes wide. "Shall we just see where the rest goes? Get out of this place and improvise?"

"I'm way ahead of you. My place is just around the corner."

***

My previous boyfriend and I broke up two months ago. We'd been together for almost a year. He liked me in a chastity clamp, keeping me nice and secure so that any orgasm I had was a direct order, and privilege, given by him. Frankly, I loved it because the times that he let me cum were so powerful, it was like the world's most addictive drug and only he held the keys.

He had plenty of fetishes that I enjoyed acting out with him. I'd be told to strip down to my garter belt and heels, kneel before him and jerk him off. When he'd get close, he'd drop down on the floor and I'd shift so that he could finish all over my feet. Providing he got enough cum on my shoe, he'd take it off me and have me lick it off.

By the time I was done, he'd be rock hard again. That's when I was expected to assume the position so that he could fuck my ass raw. Having just spent himself, he could go for upwards of an hour. This didn't happen often but when it did, I couldn't sit right for three days. And every time I shifted and felt a little shiver of pain, I sighed at the memory.

I'm not a masochist. I'm not psyched up about pain but I am absolutely addicted to other people's pleasure. It fills me with so much joy, I can barely handle myself. Even wrapped up in that chastity clamp, I swear that I felt more satisfied than him because as he lay there on the floor, gasping for breath I knew that I had caused that...it was my body that spent him and that was powerful.

This was a gift women held since the dawn of time so there was no wonder that I decided to embrace it. Yes, from a young age I felt compelled to dress as a girl and I genuinely have always been out of place as a man but when I was able to really discover my feminine side, I knew that there was more of a reason than I looked good in a skirt.

Everything else was just icing on the cake. My love for cum, my appreciation of anal sex, my desire to suck men off...all of it contributed to my need to pleasure people. I half thought about becoming a prostitute just to get paid for my own fetish but luckily I had SOME sense.

When I met this guy, I wondered if he would have it in him to tolerate the real me. I asked probing questions about his sexual interests before I made any move. The comfort level never went too high but I finally decided to just take a chance. After all, we weren't really going any further without this talk and if it worked out...well, as I said he was fucking hot.

On the way to his house, he put his hand on my leg. The warmth of his fingers through the silky stocking made me gasp. He caressed gently, running his palm up and down my thigh. Just seconds before we stopped at his house, he seemed to gather the courage to go high enough to brush against my skin.

I could tell he was a little embarrassed as we got out and headed up to the house. My heels clacked on the sidewalk and I moved with perfect, feminine grace. I had spent eight months in a dance studio, working with the woman who owned the place to learn how to move like a woman. My seductive motions were perfect.

Before we reached his stairs, he moved up next to me and cupped my ass. I smiled at him. "Do you like?"

"It's firm...you work out?"

"Every day, lover. This is all about the body, not just the clothes. If you want to pass, you have to do the work."

"It's amazing..."

Inside, he turned and pressed me against the wall, kissing me hard. Our tongues met, I put my hands on his cheeks even as he ran his up and down my sides. It tickled a little but I loved the sensation, the strength of his arms and body against me. I bent my knee, lifting my left leg so that I could hook my heel around the back of his calf.

I could feel his cock harden against my pelvis, throbbing with his excitement. It made me moan into our kiss, a frustrated desire to taste him and feel his whole body quake with rapture.

He urged me to follow him into the living room and we kissed the whole way there, stumbling and embracing, laughing and living for the moment. All thoughts of the past and future drifted away. This connection was solid and even if it might never last, it was real and we could count on it.

We arrived at the couch and he sat down, motioning for me to get on my knees. I dropped before him as he unzipped his pants, revealing his glorious seven inch cock, throbbing and pink from the way we crushed it between us. I could see pre-cum coating the tip as it twitched from the cool air in the room.

Without a word, I leaned forward and wrapped my red lips around the head, sliding down to take him into my mouth. The shaft was hot and soft against my tongue and I massaged him with it as I plunged down and up, sucking hard. His whole body was stiff, his muscles tight as a high moan was torn from his throat.

I grabbed his tightening balls firmly with my left hand, kneading them like dough. He spread his legs wide without prompting, making it easier to continue my ministrations. The moans increased and he started thrashing his head about. The couch trembled as he grabbed the cushions in a death grip. Breathing increased to the point that he was practically hyperventilating...the moans became cries...

I felt the first cord of semen coat the top of my mouth. I plunged down hard and took him into my throat, concentrating hard to let him spray at least once straight into my stomach. This made him lose his shit and the cum was hot and fast. I pulled out and let the rest of it spray on my face, several globs of it as if he hadn't fucked even himself for a month.

By the time he finished, he was a panting, sweating mess on the couch. I could taste his semi-sweet cum on my tongue and feel it chilling on my cheeks and forehead. He watched me through slitted eyes and I smiled up at him, enjoying the way he looked more than I could ever explain.

"I can't believe you did that...I've never cum like that before in my life."

"I'm just that good, baby." I winked to show him I was kidding.

"Do you want...are you going to..."

I shook my head. "I don't have to." I reached up and tugged on his cock which earned me a little convulsion from him. "Do you think you've got anymore in you, tiger?"

"I...feel like I could sleep for a week..."

I thought he'd have had more endurance than that but then again, if he hadn't had a proper blow job in a while, I could see how it might spend him like that. "Maybe we should adjourn for the evening."

"Wait!" He reached for me but missed my hand. His arm flopped on the couch. "Will you call me tomorrow? If you're not going to stay tonight?"

"Of course I'll call you, darling. You appreciated that little blow job more than anyone has in a long time. I like you."

I decided to play a little hard to get and didn't call until a couple days later. He answered the phone instantly, conveying how nervous he was that I wouldn't call.

"You could've called me, silly."

"I...didn't think it would be appropriate."

"Really? I thought the guy was supposed to pursue the girl."

"Can we...get together and talk? A little bit? Today? Like...now?"

"Sure, darling. Your place again?"

"Yeah, that would be great."

This time, I wore a plaid miniskirt, white stockings with a garter and a white blouse. The shoes still had heels but they were pseudo Mary Jane's. I even went for pig tails just to be a total perve. When he opened the door, I thought his eyes were going to pop out of his head.

"I thought you might enjoy the school girl look," I said. "What do you think?"

"I think you could be a porn star."

I laughed. "I thought about it...but I'm doing alright without it. What's going on?"

We sat in the living room, me on the couch and him in an arm chair. He looked nervous as he tried to determine what he wanted to say. I leaned back and crossed my legs, lifting my skirt a little to distract him with a shot of my pink panties underneath. He pursed his lips and finally found some words, even if they came out with a break in his voice.

"I've been thinking...since you and I talked at the club...I...it sort of...I don't even know how to say this."

"Just say it, baby. I've heard a lot. Good, bad...I'm pretty easy now." I paused. "That came out wrong."

He laughed, still nervously but at least he was loosening up some. "It's...you see, I have...sometimes thought...the way you talked about. I mean, I like the pleasuring of other people...and when I asked if you were gay...I...I'm not gay, obviously or...maybe not so obviously but I...Jesus Christ, this is hard to say."

"Take your time."

"It's...I admire you...and what you've done. I..." He took a deep breath. "I want to be like you, will you help me?" After blurting out the question, he sighed heavily. "Wow...I....can't believe I really said that."

"Neither can I," I replied. "And trust me, I'm hard to surprise."

"Are you...are you angry?"

"Angry?" I frowned. "Why would I be?"

"Because you wanted...to be together."

"There are plenty of fish in the sea and besides," I leaned forward and touched his knee. "We can still be together. But what do you mean you want to be like me? You have to be specific."

"I...wore my mother's panties when I was a teenager. My last girlfriend and I broke up because she caught me jerking off with one of her stockings. I suppressed it as best as I could but..."

"But you can't do it forever."

"Yeah..."

He looked ashamed.

"Interesting...no one's asked me for this before but...I can see some benefits."

"You can? Like...like what?"

"Like I could have a little pet project. Hell, if it makes you happy...if it brings you pleasure...then I'm sure this'll fulfill me perfectly well. But you have to be willing to work...and I do mean work hard."

"I am."

"That didn't sound very certain."

He sat up straighter. "I am!"

I smiled. "That's perfect. You want to be just like me? Submissively female? Taking it from people even at the expense of your own release?"

He nodded, blushing.

"Then get over here on your knees and prove it to me." I lifted my skirt. "Suck my fucking dick."

"Er...what?"

"Get on your fucking knees, bitch and suck my cock. I'm not going to tell you again. Either your serious about this or you're not. I want you to get my dick soaking wet with your spit and when you've got me rock hard, I'm going to drill your ass like the little girl you are. That's my test. Pass it and we go through the basics."

"Isn't that..."

"A trial by fire?" I asked. "Yeah, fuck it. You've waited so long, I want to cum and you're going to help me. Besides, I see the way you're looking at my panties. You're practically salivating aren't you?"

He nodded.

"Yeah, because when I was sitting where you were, I was in the same place. So..." I motioned. "Are you going to get started or are you going to do this all alone?"

He dropped to his knees and crawled to me, nudging my knees so I'd spread my legs. His fingers lanced through the waist band of my panties and tugged.

"No," I said. "Just pull them aside. A woman doesn't have to take her panties off to get fucked or eaten out. Just move them out of your way and get that mouth working."

He carefully pulled them away from my small, tucked penis which sprung out as soon as it was free. It was getting hard, half massed really but as soon as I felt his hot breath against the head, I felt heady from the rush. "Slowly...put your mouth around it and suck down the shaft."

I coached him through the first five plunges, up and down...use the tongue...suck a little more...watch the teeth...he was a fast learner or a natural born cock sucker and as he continued, I felt myself getting warmer. "Suck on my balls."

He drew back and held my cock firmly in his right hand, giving it a gentle stroke as he leaned down and licked at my scrotum, sucking my nuts between his lips and caressing them with his tongue. I thought I'd explode on the spot. I rarely allowed people to give me a blow job but this guy intrigued me. The whole idea of helping him...of bringing him over...I was turned on like there was no tomorrow.

"That's enough," I gasped. "Get your fucking pants off! I want inside of you."

"Please..." He muttered. "Just cum on my face. I'm not ready for the other..."

"Really?" I asked. "I thought you wanted to be like me. I thought you wanted to live for other people's pleasure."

Without a word, he stood, dropping his pants and bending over the arm of the chair. "I want to feel your excitement," he said. "Make my body yours."

"Thank you." I saddled up behind him, bending to lick his ass. There would be a lot of changes on this boy and most of them started with a razor but today, he'd learn what it felt like to be pierced by a cock. It would not be the last time and certainly not the most painful but before I was done, he'd be truly ready to start his path.

The second my tongue touched his asshole, he started moaning. I saw his cock get hard and smirked. We'd be putting a chastity clamp on that right quick. But for now, he could get as hard as he wanted. This was just round one of my long term plan.

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