A Transvestite Love

"Are you sure you want to go inside?" Heather asked.

"Of course. I mean, we've come so far, haven't we?" I said.

"But you know what I am." Her eyes seemed sad – her tone emotionless. Just moments earlier we were having dinner and those eyes were bright and the conversation cheerful. It was like we were in another world, but now reality was sinking in.

"Look, I know who your are."

I paused for a moment. She was so beautiful. Long blonde hair, soft facial features, full breasts and a narrow waist with the tightest ass that shaped the silver sequined dress she was wearing nicely.

All night I kept admiring her shapely toned legs within her shear hose and sexy straps on her high-heels that tied around her ankles. Her dress was shoulder less and her lips were soft and full.

She was undoubtedly the most beautiful woman I had ever seen, much less been out with. No one would ever imagine she was a man.

"What matters is not what you are...it's who you are." I said.

Heather's eyes brightened. She put the key in her apartment door.

For the record, my name is Brad and I'm not gay. Well, not clearly gay. Maybe, I'm bisexual and a closet one at that. It's like I told Heather.

In college my roommate and I experimented, I guess is the best way to put it. For him, it probably was more than an experiment because he now lives with a guy. He and I had sex maybe a dozen times in the dorms during that last year – or last month really.

It started as a dare – a dare that we both knew arose out of curiosity about having sex with another man. By the third time we were fucking like crazy – to heck with dares and curiosity.

It was already near the end of our senior year, so we had to make a decision. To be honest, I loved the sex with him. It was hot, steamy and incredibly sensual. My yardstick had been fraternity girls who were absolutely gorgeous, but something was missing in bed with them.

Now you'd think a soft woman would be more sensual and I had a few that came real close. But they lacked intimacy. Yes, intimacy.

I know that sounds odd. But imagine my sexual experiences with the fraternity girls. Dinner, drinks, getting to know each other – then when you finally make it to bed with one of these beauties there ends up being rules at some point.

One wanted the lights off during sex. The other liked just one position. Quite a few hated blowjobs and virtually none would do something as kinky as anal. I'll admit I've had some wild sex with the fraternity girls and women after college – but when compared to sex with my roommate it was clearly different.

There was no drama having sex with another man. Inhibitions were out of the question and we did anything we wanted in bed. While I had to be macho to a certain degree and play my role in bed with women – there was no such restriction with my roommate. We could be macho or vulnerable – passive or aggressive. There were no limits it seemed and the sex was steamy.

Nevertheless, the end of college was the end of mansex for me. My roommate was brave and moved on, I guess. But I still liked women. I was attracted to women, their breasts, ass and soft skin. I just couldn't seem to find the intimacy I had found in bed with a man – I know it sounds strange.

Then I saw Heather. She won't say what her name use to be.

She worked at a bar I visited. A friend immediately pointed out that he heard she had been a man, did the hormone thing a long time ago but kept to herself. It seems at first she thought the guys at the bar hitting on her knew she was a man or at least once was a man for the most part.

After all, she was more beautiful than all the women at the bar. She has long hair, voluptuous breasts, soft voice and a sexy figure. Who would know?

But when the guys find out, they are embarrassed and cruel. Word gets around the bar quickly so she just keeps to herself. If it were a gay bar, I guess it would be different. But Heather chooses to work at the macho spot in town. So gorgeous or not, she has avoided male contact for a while – just like me, I guess.

I'm a trainer at a local gym. If the guys at the gym found out I had closet homosexual interests, I'd be toast. But when I started frequenting this bar I was naturally attracted to Heather. A friend saw me eyeing her and laughed. He then told me that he had heard she had a dick under that dress. It was supposed to turn me off. It had the opposite effect.

I had begun to wonder if someone like Heather was what I needed. The elements of a woman I need and the elements of a man I want. What could be better?

Curiosity raised its head in my mind again. Just like in college.

I secretly flirted with Heather. She tried to keep her distance. She wouldn't give me her number as she thought I was just setting her up for some joke. Apparently, she had been hurt before.

I finally got her to agree to meet me at a neutral place, just to talk. We had coffee that first time. I was clearly going to have to win her over.

That was when I confessed about my past sexual experience in college. She was the only person I had told in this new city, which I had moved to after college in attempts to grow my physical fitness business. I made it clear that I hadn't been with a man since college and to be honest, I wondered if my same sex interest had been just situational.

But the more I thought about it – the more I longed for that experience again. I told Heather that hearing she had a dick not only didn't bother me – it was just one more reason to be attracted to her.

Nevertheless, it still took a few times going out – sharing stories, dinner, coffee. Slowly we gained trust. This would be the first time she invited me back to her apartment and we both knew why.

She craved a man since moving here and so did I. But neither had found someone to trust – to be intimate with. I guess we both wondered if we were making a mistake or not.

I had kissed her cheek after our last night out together. I know, you'd think we'd just fall in bed, right?

As we entered her apartment and the door closed, I was suddenly nervous – like a kid on his first date. She put down her purse, kicked off her shoes and showed me around. It was nice, cozy and quite feminine.

The kitchen was small and had a dining area and small living room all in the same general area, so the tour was fairly quick. She pointed out the bathroom and then her bedroom.

"Hmmm. I'd like to go in there." I said.

"Well, I've not had a man in there." She replied.

"How about a woman?"

"No. Just me. I've tried to keep to myself since moving here." She laughed. I could tell she was nervous as well.

As it turned out Heather had been pretty much monogamous during her homosexual years, as she called it. She even went so far as showing me her negative infectious disease tests and such during one of our chats – I guess she feels self-conscious having been without a partner for a while.

I walked in the bedroom. Lace window treatments, satin sheets, everything neat and in its place – including lube on the nightstand.

"You were expecting me I see." Pointing at the tube. After I said it, I almost wished I hadn't.

Heather's eyes widened.

"No. I...well, masturbate sometime, you know. And a dildo from time to time is nice." She straightened out her dress and looked down.

"Listen, Heather. I haven't gotten up the nerve to approach a man since college. Then I met you. " I touched her chin and lifted her face. "I want you and I didn't think I'd ever say that to a...well, man...again."

Heather's eyes met mine.

"Is it the woman in me you want or the man?" she asked.

"Both." I said. Then slowly I leaned toward her. She closed her eyes. Our lips met.

Her full lips were soft – softer than any woman I had kissed in fact. Gradually I licked her lips in between breaths. Each lick tested her willingness to give herself to me and quite frankly, I was testing my own willingness to give myself as well.

Soon her tongues ventured out. They touched tentatively at first – then I kissed her deeply, thrusting my tongue between her lips. It found hers and our tongues swirled as our kiss deepened.

My hands rested on her hips and soon found her tight ass. She caressed the back of my neck and back. As I kissed her neck, she moaned softly. I found the zipper on the back of her dress and she didn't stop me as I unzipped its length.

It fluttered to the floor and she grabbed my erection that was tenting my pants between us.

"Do you know how long it's been since I've touched another man's dick." She said.

"Not as long as me."

After that, I have no idea how we got naked. But suddenly we were. I remember peeling off her bra and was amazed at the perky fullness of her breasts, which contrasted sharply with the erection between her legs once she rolled off her pantyhose.

I remember that part of our quest to get naked because it was so incredibly sexy and was the only moment as clothes flew everywhere that time seemed to stand still yet flash quickly.

Our naked bodies still connected by a passionate kiss with limbs entwined collapsed on the bed beside us. I groped for her ass and my pelvis grinded toward hers and hers toward mine.

I felt our erections pressing between us - the smooth underside of each meshing with the other. My desire to penetrate her somehow was suddenly overwhelming. My dick stroked against hers and for a moment we simulated fucking as we kissed – each pelvis gyrating toward the other.

I kissed Heather's neck then sucked her soft breasts –first one then the other. Her skin was smooth and she moaned softly as I showered her body with kisses.

She soon pushed me onto my back and took my throbbing dick into her mouth. Past her luscious lips and over her wet tongue my erection slipped until I penetrated her mouth fully.

I brushed her long hair from her face as she suckled my dick. She devoured it like no one had before her. Soon I was lifting my pelvis to her mouth while running my fingers through her hair.

Sucking sounds filled the room and my desire grew. My hand wandered down to the small of her back as she sucked - then over her round, tight ass. My finger found her asshole easily and I tested the rim of it with my fingertip. Heather moaned softly.

She continued to suck me as I reached the bedside table and retrieved the lube she had left there. Squirting a glob on my finger, I resumed my probe of her pink asshole only now I was able to insert the tip of my finger and test the inner portion of her ass.

Slowly, I sank a finger into her ass. Deeper and deeper it went until her moans greater louder. She relaxed her sphincter and soon I was finger fucking this beauty's orifice.

With my finger still impaled within her, she released my erection from her lips and leaned up to my face to kiss me. Our tongues mingled again and I continued to hold her by her ass. I could feel our dicks bumping each other as our passion grew.

My finger slipped from her ass. I then rolled her onto her back. As she lay on the bed below me, her eyes seemed to be pleading for me to make love to her. Heather smoothed her long hair back revealing her feminine features – full lips, high cheeks and a smooth neck.

Her nipples were erect and she spread her legs to allow me to settle on my knees between her thighs. It was a surreal sight.

The feminine vision of a beautiful woman was laid out before me – narrow waist, full breasts, gorgeous eyes and a soft voice along with a gentle touch. Her legs were silky smooth and she spread before me revealing the soft pink sphincter of her tightly packed ass.

Her ass was inviting. Her hips writhed slightly in anticipation, as she desired our union. The surrealism was found in the erection just above that lovely ass of hers.

Her testicles were pulled tightly against her body and her dick was hard and smooth. It matched my own erection, which glistened from the saliva of her sucking me.

I squirted lube on my dick. It glistened more and became slick with goo. I then leaned over her – kissed the tip of her dick, then breasts. I leaned further, my slick dick now bumping her ass and briefly kissed her lips.

"I want you Heather." I said.

"I want you even more. Fuck me." She whispered.

With her words still lingering in my ears, I grasped the base of my dick and pushed my erection against her folds of her tight sphincter. Round and round I encircled the rim with the tip.

Heather relaxed and yielded herself to me. The head of my dick began to slowly melt into her asshole. It's soft crown molded with the tightness of her sphincter until the base of the head slipped over the rim of her asshole. With a subtle pop, I penetrated her and was rewarded with a gentle moan from her lips.

My hard erection then followed. The lube allowed me to slide easily into her – the shaft disappearing ever so gradually into the depths of this surreal beauty.

As I impaled myself within her, I leaned over her so that we were face to face. Her dick throbbed between us as if it had a pulse. Slowly I gyrated my hips back then forth and began to slowly fuck her.

Our eyes drank each other in. She opened her mouth slightly but made no sound. Her eyes never left mine.

My dick was warm. She would fully engulf its length, gripping it with her ass before allowing my gentle withdrawal. When the head of my dickhead met the inner rim of her ass, I reversed my hip gyration and push forward once again. Heather's ass would relent and she'd close her eyes briefly as the full length of my shaft disappeared within her only to repeat the fucking motion over and over.

Soon it was as if the base of my spine were on a swivel - like a hinge I thrust forward with my hips – softly at first then faster and faster with a gradual increase in speed and intensity.

Heather's ass loosened to accept my penetrations. She spread her thighs even wider and her dick bounced on her abdomen with every thrust. Sweat began to bead on my forehead. Involuntary grunts began to escape my throat and Heather started to moan softly at first, then louder with each ever-increasing thrust.

"Damn you're beautiful." I said.

"I love your dick. Fuck me." She said.

"You're ass is so tight." I replied. My breath was getting shorter.

"Fuck my ass. Oh, fuck me."

"I want to cum."

"Cum inside me."

"Oh shit, Heather. I'm going to cum."

"Cum baby. Cum in me."

My ass tightened. Moans filled the room that seemed inhuman. The musky scent of sex filled the air. For a moment, time stood still as we consummated this surreal union.

My skin began to tingle. My muscles trembled. My body began to spasm, then I felt it...

"Heather, I'm gonna cum..."

"Fuck me, baby."

"I love your body Heather. Damn, I'm cumming...I'm..."

Lights flashed before my eyes. My ass clinched tight. I thrust forward forcefully into Heather's ass.

I felt a spasm within my dick. It pumped involuntarily as my entire body seized. I could feel streams of cum shooting through its length and spraying within my lover.

Heather quickly reached up and grabbed her own erection. She pumped furiously then threw her head back as streams of pearly white fluid erupted from the tip of her dick. A barely audible groan escaped her lips as trails of cum fell in long lines between her breasts.

The room fell silent except for our chests heaving for air. A musky scent wafted through my nostrils. It was intoxicating.

I looked down at Heather as she lay below me. My dick was still trembling in her quivering ass. She released the grip she had on her dick. It flopped on to her flat abdomen then slowly began to lose its erection.

She opened her eyes. We smiled at each other.

I leaned down and tested a string of white fluid that rested between her breasts with my tongue. It was salty. Slowly I licked one line, then another. Heather ran her fingers through my hair as I cleaned her smooth skin.

Occasionally, I would suck a breast then the other before continuing. I licked until all the sticky fluid was gone. When I leaned further up to kiss her neck then lips, my softening dick squished from her asshole.

Stroking the hair from her cheek, I looked again into her eyes.

"I could get use to this." I said.

"You think so?" she asked.

We actually talked for a while – naked, still flush from sex. I talked about my last sexual experiences with a man as an experiment with no real lasting meaning. She talked about her last experiences as a few brief superficial fucks.

"That was the first time I think I've made love." She said.

I assured her – it wouldn't be her last.