Isabelle

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A man's first encounter with the other sex.
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Kary_M
Kary_M
433 Followers

After my divorce and moving back to the city into a little two room apartment on the third floor of a remodelled office building. It was smaller then the house I was still paying for but at least it was on a front corner so I could watch the world go by.


Within a month I had gotten real tired of nuked food and found a small diner about a block away. It was cheap, but the food was good and the helpings always just enough to be satisfying. All in all it had a nice comfy home like atmosphere with friendly waitresses.

For the most part the girls where just teenagers, working part-time while going to school. Isabelle was the exception. She seemed to be around my age, early thirties, long blonde hair always tied back and a thin but well proportioned figure. I found myself always trying to sit in her section for an excuse to get to know her.

After a couple weeks of eating at the diner three or four days out of seven we started to chat and flirt back and forth like old friends. I thought about her often and began to fantasize, dreaming of what Isabelle looked like naked. Every time I saw her I thought about asking her out but for some reason I always chickened out. I like to think my uncertainty was because of my resent divorce but it really was the fear of being rejected in front of everyone at the diner.

Then one Tuesday night I lucked out. Isabelle had taken off her apron getting ready to leave looking out the window at the heavy rain falling.

“I’m going to be drench by the time I get home.” She said to herself.

“How far are you going?” I asked.

“Just a block or so,” She replied shaking her head, “But that’s far enough with out an umbrella. It was sunny enough this morning and I didn’t think I’d need it.”

“I’m almost ready to leave,” I tried to say nonchalantly, “Which way do you have to go? My umbrella is big enough to share.”

“Down towards Fifth Street.” She said with a hopeful look.

“Same as me.” I told her even though I would of lied anyway just for a chance to have a private word with her.

“Oh your such a dear, thank you.” She beamed at me and laid her hand on my shoulder, giving me a rush of excitement before going into the back of the diner.

Isabelle was waiting at the door buttoning up her jacket when I finished paying my tab. Out on the street she took my arm and squeezed up tight against me under the umbrella. The contact made me feel as nervous as a teenager. My palms began to sweat and my groin started to stiffen. I felt myself suddenly tongued tied, not know what to say never mind how. Isabelle was talking but I couldn’t seem to concentrate on what she was saying feeling her breast rub against my arm.

Before I new it she had stopped in front of a building directly across the street from mine.

“Here we are,” She said turning to face me, “How much further do you have to go?”

“Just across the street Isabelle.” I replied in a shaky voice.

“All this time,” she laughed, “We’ve been neighbours and didn’t even know it. You can call me Izzy if you’d like.”

“Thanks Izzy,” I replied, then took the plunge, “I’d like to see you some time, other than at the diner, if you’d like maybe dinner and a movie or something?”

She looked into my eyes and grinned. Then so quick I almost missed it, she reached up and kissed me on the cheek and whispered maybe before turning and running into her apartment building. I stood there dumbfounded not even realizing the rain was soaking my uncovered head. Izzy turned before closing the door to giggle at me in my stupor. I felt a little foolish as I crossed the street to go home but I also felt real good about my prospects.

That night, I found myself sitting by my window in the dark. Looking out into the rainy night. My eyes kept going over Izzy’s building wondering in which apartment she lived in. I noticed a light come on in a window directly across from me and hope surge up through me. All I could see was long blonde hair draped over a dark robe. Grabbing the binoculars I always kept behind the chair I focused in through the window. I had a clear view through the window into the bathroom while the blonde stood bent by a tub adjusting the taps.

I was delighted to see as she turned to look into her mirror and tie back her hair that it was Izzy. I could not believe my luck as my excitement built immediately. Turning her back to me and sliding the robe off of her shoulders stepping into the shower spray I got a perfect view of a nicely rounded bum. It was even better looking than I imagined. I watched as she turned to soap her body getting a look at a very well formed pair of firm looking breasts. I could still feel were they had rubbed against my arm on the walk home. I started to pull on my penis as she soaped her tits. I could see her pulling on her nipples with her head back and a look of pleasure on her face.

I was really getting into my private show, getting almost to the point of blowing a load when she turned off the water and turned to step out. I dropped my glasses downwards hoping to see some pussy. I came just as the shock of what I saw registered in my brain. My dream girl had a cock.

At first I felt repulsed and cheated, how could she do this to me. How could I face her again knowing what I did of her now? I couldn’t get the image out of my head. She had such a perfect looking body except for that one thing. I looked down at my groin and the cooling seed that had collected in my pubic hairs. I was still hard, why I thought. I’ve never thought of penises before. I couldn’t even remember ever having those gay kinds of thoughts before. Every time I closed my eyes I could see it in minute detail. A thin uncut semi erect penis about five inches long attached to a gorgeous woman and it was turning me on.

The rest of the night I tried everything I could think of to get Izzy out of my mind. Nothing seemed to work and the worst part of it all was I started to feel guilty about spying on her. Part of me felt repulsed while another felt excited and I just couldn’t understand that part at all. I spent a long restless night trying to sleep and when sleep did come I had vivid dreams of having sex with Izzy.

The next few days I avoided the diner eating at home and at work. Unfortunately I was constantly distracted by thoughts of Izzy and every day they became more intense. When Friday arrived I couldn’t take it any more and thinking if I faced her I might help me get over it. Screwing up my nerve I entered the diner and was greeted with a warm smile and hello from Izzy. I sat down quickly at the counter instead of my usual booth. Mostly to hide the instant erection I got when I laid my on eyes on her getting immediate visions of her naked body. My God I thought this seemed to make it feel worst. I stuttered and stammered while she took my order and giggled at my discomfort. Luckily for me the place got busy so she didn’t have time to talk while I ate. I’m sure in my state I would have probably bitten my tongue.

I’d finished eating and sipping on my coffee thinking about what I should do when I felt a brush against my back and Izzy sat on the empty stool beside me.

“I’m off in about twenty minutes,” She stated looking into my eyes and smiling, “Does the movie offer still stand?”

I felt instantly trapped and tried to think of a good excuse not too but I couldn’t. Then I thought that I could just go to a movie with her then never ask her out again.

“Sure,” I replied then lied, “It will have to be an early night, got to work tomorrow.

“Me too.” She said smiling and got up to finish her shift.

I felt like an ass for lying as she refilled my cup with a wink. While I waited for Izzy I watched her work. She moved with feminine grace across the diner wiggling her hips seductively. I tried to make myself believe that I only imagined what I saw through the window. The movie was uneventful except that she leaned into me rubbing her firm breast against my side all through it. I don’t remember much about it sitting there sweating with a hard-on made it hard to think about anything. Except for Izzy, she was beautiful to look at and she smelled good. Everything she did seemed so feminine but my mind kept going back to the vision of her penis.

After the movie we stopped for a drink at a small corner bar and talked. I know I did talk but the only thing I remember was that she had a glass of white wine. Before I knew it, we were standing on the steps of her building. Izzy was standing on the top step one above me so that that we looked eye to eye. She really had nice blue eyes.

“I really had a nice time tonight,” she smiled, “Thank you.”

“So did I Izzy,” I found myself saying, “Maybe we can do this again?”

I don’t know why I said it that certainly wasn’t my plan. But I realized that I had meant it.

“Okay, sure,” She said looking down, “But first there is something you should know, no something I have to tell you about me. Why don’t you come in, we’ll have a glass of wine and I’ll try to explain it to you?”

I swallowed and tried to look stupid. I knew what she might want to tell me but I didn’t want her finding out how I knew.

“Sure,” I said, “A glass of wine would be nice.”

“I hope you feel that way after?” She said nervously turning to lead the way into the building.

Izzy’s place was much the same size as mine, but had a separate kitchen. The only place to sit was on a sofa along the wall facing a small TV. She sat beside me on the edge of the couch her knee was almost touching my leg. We sat in silence as drained her first glass then half of her second. Then she took a deep breath and sighed looking into my eyes. I could tell she was nervous and a look of fear seemed to cloud her eyes.

“I’ve never met anyone that made me feel the need to say this too. But I really like you Dave.” She started, “I’m not what I appear to be.”

She looked into my eyes before draining her glass and looking down again.

“You do know what a transsexual is don’t you?” She asked.

“I think so.” I replied trying to act dumb.

“I always felt different when I was little,” She began again, “like I didn’t feel normal and when I hit puberty I realized why.”

She stopped to fill our glasses keeping her eyes down the whole time.

“What I’m trying to say is that I was born a boy. When I realized that I was trapped in the wrong body I started to make changes in my life. I’m very happy with who I’ve become except that I am lonely. That’s why I’m telling you this. I like you and I’d like us to be more than friends.”

She looked up at me and continued, “I’ll understand if you hate me and never want to see me again.”

She looked down at her glass in silence while I thought that her words verified what I already knew but had hoped wasn’t true. Something seemed to come over me as stared at her. Maybe it was the fact of all my thoughts for the last week or maybe the perpetual hard-on of the last four hours was driving me. I cupped her chin in my hand and raised her face to look into her eyes.

“Izzy you’re beautiful,” She blushed, “I like you too and what you said doesn’t change that. I’ve never even thought about this kind of thing before and I can’t say what will happen, but.”

Suddenly I was at a loose for words. Looking into her deep blue eyes and not even knowing if I could I leaned towards her until our lips met. Izzy gently leaned into me for a moment before our first kiss was broken. We sighed together causing her to giggle. She slid back further on the couch and pressed her body against mine. Her firm breast pushed up against me as we kissed again. This one lasted longer as our tongues danced together for the first time. I moved an arm around her shoulder and the other fell to her waist. I could feel her tremble under my hand as she moulded her body against mine.

Then I felt a hand rest on my thigh about an inch from the end my throbbing erection and shivered feeling it slid up and over it. “Mmmm,” she moaned breaking our kiss, “I’ve been looking at this beauty since you came in the diner today. So many times I almost reached out to grab it.”

She giggled like a little girl as her hand slid gentle up and down the length. I groaned into her neck as I kissed down to her shoulder. Reaching up grasping her breast I was amazed that it felt so firm. I could feel the nipple swell instantly under my fingertips. I fought with the buttons of her top as she worked the zipper of my pants. My cock was out and her fist was moving slowly up and down my shaft before I managed to unbutton her top half way. Izzy grabbed her shirt and ripped off the remaining buttons. The clasp was on the front of her bra and was unhooked easily. I found myself staring at the most perfect set of tits I’ve ever seen in real life before. Alternating from breast to breast teasing her nipples erect, I leaned back to watch as Izzy played with my penis, cooing as the foreskin covered then revealed the glans with each stroke.

Izzy turned to me with an impish look on her face then swooped down sucking over half of my seven inches into her mouth swirling her tongue as she fucked me with her mouth. In moments my body tensed and I tried to hold off from cumming. This felt like the best blowjob I’d ever received in my life. Izzy must have sensed my attempt to hold back and doubled her efforts. In moments my orgasm crashed down on me seeming to come all the way from my toes as I shot volley after volley into her mouth. I could feel Izzy’s throat working to swallow as my load pumped into her mouth. She seemed to be purring in satisfaction the whole time. She kept sucking and tonguing my penis as it softened sending little jolts of pleasure up my spine until she felt it start to harden again.

“Looks like he’s not finished yet.” She giggled, “What do you think he wants to do next?”

Izzy moved up and rested her head on my shoulder leaning her body onto mine and stared into my eyes with smouldering look.

“I don’t know,” I replied trying not to let my nervousness show, “what do you suggest?”

“Why don’t we get naked and go somewhere more comfy.”

Izzy started to undue the buttons of my shirt as a sweat broke out on my body. I hate to admit but I kind of felt a little scared about the situation. Sensing something Izzy sat up and looked into my eyes and gave me that impish smile again.

“Don’t worry sweetie, I’ll be gentle. I won’t make you do anything you don’t want too.”

It wasn’t what I didn’t want to do that I was worried over. It was what I wanted to do that was scaring me. She stood and held out her hand to me. I took it, rose and followed as she led the way to her bedroom.

Once we where beside the bed, Izzy turned to face me and dropped her shirt and bra to the floor. In a blink of an eye she had my shirt undone and off. Sliding a hand on each side of me, she started to push my pants down leaning towards me. Then she did something no ones ever done to me. First she licked then suckled each of my nipples causing me to moan and shiver. I could hear her elicit a soft giggle.

I rested my hands on her shoulders as kneeled in front of me pulling down my pants and removing them and my socks to join the growing pile of clothing. Then moving her hands up to play with my buttocks. The whole time she spent sucking once again on my cock almost taking the shaft completely into her mouth. Izzy was as talented as she was eager when it came to sucking cock. Only this time as she sensed my body tensing, she released my penis and stood to grind those perfect tits of hers into my chest.

I felt as nervous as the time I lost my virginity as I lowered my hands down her back to the top of her skirt. My palms, sweaty and shaking fumbled with the clasp and zipper as our tongues played together. Once past her hips the skirt fell to the floor and my hands fondled her naked cheeks. The globes were firm and smooth and Izzy moaned into my mouth as shudder went through her body as I traced the edges of the thong she wore down into the cleft of her ass.

Izzy broke off our kiss and smiling she turned her back to me. Standing with her thighs together she took each side of her thong and bent at the waist to lower them. The whole time she peered over her shoulder to watch me as I watched her. She looked so perfect standing there with a garter belt and stocking tops framing her cute ass as the white thong slowly slipped down her shapely legs.

I watched as piled pillows in the centre of the bed and laid over them so her hips were raised. All the while keeping her thighs together, hiding her secret from me. She looked back over her shoulder at me and winked.

“Well?” she asked in a throaty voice, “Are you going to make love to me or just stand there staring at me?”

I stood there in a stupor for a moment as that question sank in. Moving onto the bed I straddled her legs and ran my hands over the back of her thighs over her ass and across her back to her shoulders. Gently squeezing her thin neck before trailing my fingers down her spin then between her cheeks pulling them apart to see her pink rosebud patiently waiting for me.

“That feels so good.” Izzy moaned, “There’s lube beside the bed dear.”

I thought about that as I massaged her ass. Looking at that pink ring and an urge came over me. This was a day of first for me and I suddenly thought that I’d get in as many as I could. I took a deep breath and lowered my face between her ass cheeks and kissed her hole. I’d never have had done this sort of thing before. I never even had any kind of anal sex with my ex-wife. As I began to lavish her asshole with my tongue like it was my last meal.

My tongue was rewarded by her groans of pleasure. I could feel her hips shake and quiver between my hands as she pushed back towards my mouth.

“Oh yeah babe I like that,” Izzy cooed, “Eat me out, get me nice and wet for your big cock.”

Her words inspired me to drive my tongue past her sphincter orally fucking her ass to her groans and shivers. Rising up I placed the head of my penis against her anus. Rubbing and teasing her while spreading my saliva over the opening of her love canal. Izzy reached back and pulled her cheeks apart making the orifice to open slightly. I spit onto the end of my cock and spread it over the glans before pushing it into her ass.

I watched in amazement as I slowly sunk into her. The ring of flesh stretched turning almost white until the head pasted through and then squeezing on to the shaft turning pink again. Izzy groaned constantly between encouraging me to fuck her harder, deeper and faster. By the time her ass cheeks were slamming against my belly I could feel my orgasm growing.

“Oh yeah,” Izzy groaned, “ You fill me so good. Shoot that hot seed into me baby. Fill me up with your cum.”

Her words through me over the edge and driving deep I shuddered through another orgasm spewing cum into her as she sighed. Covered in sweat and totally drained I fell on top of her trying to catch my breath.

“ That was great.” She sighed and shivered.

We rolled onto our sides. Izzy kept a hand on my hip keeping my softening cock buried in her ass as we lay there recuperating. Her sphincter spasmed intermittingly grasping then releasing around my cock. I reached around her and stroked her breasts gently, first one then the other. I moved my hand across flat stomach until I reached her groin. For the first time in my life I touched another person’s penis. It was hot and hard with a wet sticky fluid smearing the glans. Izzy’s cock almost disappeared in my fist, the end of it was all that wasn’t covered as I looked over her shoulder. It was about an inch in diameter and her sack looked small drawn up tight to her groin. Sliding my fingers down I could feel the thumb size testicles within and it made us both shiver and Izzy groaned. I moved my hand up and gripped her penis once more slowly jerking up and down while I watched her face.

Kary_M
Kary_M
433 Followers
12