I entered the hotel bar alone, nervous about my first time alone in public while dressed as a woman. I was really hot tonight, wanting a man in the worst way, a gentleman who would appreciate my special charms. The red dress I was wearing really looked great, classy and sexy all at once. I was really looking forward to this, my first big night out. I paused at the entrance to the bar, a tingle of excitement running through me as I stood there on display, allowing myself to be seen by all in my sexy red dress.
Hmmm yes, the red dress. An acetate and spandex fabric called slinky knit, knee length, long sleeves and very low cut. Wow, what a dress! And it fit like a glove too. I had created some cleavage, using tape under my breasts, and this dress allowed me to show it off. Several inches of cleavage, along with my realistic breast forms, gave me the look of being really stacked, and I loved it. Black patent 4" heels caused me to sway my hips in such a feminine manner. I was really excited about the way I looked tonight. Excited, and nervous, but I needed to be calm if I was going to pull this off.
Getting ready at home earlier, I got rather aroused. Just putting on a black garter and stockings, lacy black panties and bra was enough to get me going. My hands shook with excited anticipation as I did my makeup. At last, I could slip on my new red dress, along with my blond wig, and check myself out in the mirror. Wow, I thought, what a babe I made. I knew I'd be having fun on this night.
Sitting at a small table in the bar, I ordered a drink from the waitress. Looking around the dimly lit room I noticed several men, sitting at the bar and at tables alone, and all of them were looking at me. Checking me out, actually, and I'll bet they liked what they saw. This was a new experience for me, sitting alone in a bar, surrounded by men and hoping to get picked up. A shiver of excitement ran through me as I thought about the possibilities. God, I thought, I really love this red dress and the attention it brings me.
The waitress brought my drink, saying it had been paid for by the gentleman at the far end of the bar. I looked in his direction, gave him a smile, and held my glass up briefly, before taking a small sip. He smiled back at me, then got up and came over. I stiffened a bit with the uncertainty that nervousness can bring. I hoped I could actually pull this off. "Hi," he said, in a friendly tone, "may I join you?" I smiled and gestured toward the chair next to me. He was certainly handsome enough. He was perhaps in his late 40's, about 6' tall, slightly graying at the temples. Distinguished looking is the phrase that comes to mind.
"Hi," I said, smiling and trying my best to sound like a woman. "I'm Ella. What's your name handsome?" I allowed him to gently take my hand briefly, but I was really nervous and I hoped it didn't show.
"I'm Tom." he replied, looking directly into my eyes. Whoa, I thought, this guy's a come on for sure. "Tom Bennett, from Detroit. Just in town for a seminar, and very bored. Nothing to do in the evening except sit in this bar and drink. Until you came along, that is. I really like your dress, by the way. Sexy indeed." His warm smile indicated he was really glad to have a pretty girl to talk to.
"Well, Tom Bennett from Detroit, pleased to meet you, and thanks so much for buying my drink. That was sweet of you, and I'm glad you noticed my dress." I smiled at him, then lowered my arm and lightly touched the back of his hand. "I'll just bet we can find something a little less boring to do this evening," I said as I lightly stroked the back of his arm. The look in his eye told me he was very interested. I slid my chair a little closer to him, hoping to get things started soon.
We talked and laughed for an hour or so. Tom bought us both a second drink, which had the desired effect. I was slowly relaxing and loosening up. In fact, I had a bout with the giggles over a silly looking guy at the bar. Finally, I was able to get close enough to Tom to get my hand on the inside of his leg. He made a little sound that could have been a moan, as my hand slowly rubbed the inside of his leg, missing his cock by only an inch or two.
He got the idea though, suggesting we get fresh drinks, and retire to his room for a more intimate conversation, as he put it. I smiled warmly and said, "I'd love to. I thought you'd never ask." With that I allowed my hand to lightly brush his now growing erection, as he gave another little moan.
We hurried to the elevator, and after we were in he took me in his arms and kissed me passionately, over and over, exploring my backside with one hand while holding his drink in the other. I loved it, and let him know it. Between kisses I said, almost breathlessly, "Why did it take us so long to get to this point?" His embrace became a little more passionate as I said it. Finally, the door opened and we rushed down the hall to his room. Once inside he kissed me again and again, as his breathing became shallow and more rapid.
"Tom," I said, breathing a little hard myself, "I really want this," as my hand began stroking his now rigid erection through his pants, "in my mouth baby." I fumbled with his belt, finally getting it loose, then knelt before him as I pulled his pants and shorts down. On my knees now, I purred with delight at the sight of his beautiful cock inches from my face. I licked my lips in anticipation of what was about to happen. "Oh Tom, you're wonderful," I said, "I can't wait." I leaned forward a bit, took his cock in my hand and kissed the head, then began moistening it with my tongue. He moaned with pleasure, as it stiffened more, veins bulging and the head swollen. A small drop of come emerged, which tasted wonderful. I knew I wanted more of that.
Slowly I took the throbbing, swollen head into my mouth, as he gasped with delight. I moved my hand down to his balls and slid my mouth down his rock hard shaft until he was all the way in, then slowly withdrew it, until only the head was in. Slowly I slid my mouth back down, then withdrew again. He exhaled slowly, gasping with lust. With each withdrawal I swirled my tongue around his shaft, lubricating it further. He was gasping and moaning with sheer pleasure, as I slowly sucked his magnificent, growing erection. A little faster now, as I took it even deeper, until my face was buried against his groin, then withdrew, my tongue doing a swirl, then quickly sucked it in again.
Tom began responding to my rhythmic motion by thrusting his hips into me as I slid my mouth down his shaft. His hands found their way to the back of my head, as he pulled me into him. "Oh baby, I love this. Faster baby, faster, deeper," he said breathlessly, his passion like a runaway train. By this point Tom was doing all the work, thrusting his hips and driving his hot cock deep into my throat, while pressing his hands to the back of my head, pushing my mouth as far down as it would go. He was, quite literally, fucking my face, and I loved every second of it, my arms wrapped tightly around his hips.
Finally, but really too soon as well, he stiffened even more, and his thrusting became almost frantic, as he gasped and moaned in sheer passion. "Oh baby," he moaned, "that feels so good. More baby, more." He thrust his swollen member deep into my throat one final time as he pulled my face tightly into his groin, and climaxed with an explosion of sweet, delicious come.
He held me there, my face buried in his pubic hairs and my mouth impaled on his cock deep inside me, as spurt after spurt hit the back of my throat, his swollen cock recoiling with each spurt. Somehow, I swallowed it all without choking, and loved it. After what seemed like forever he released my head, but all I did was slowly suck him again, hoping for more of that delicious come. Happily, I was rewarded with a couple of final spurts. Tom was now completely spent, and collapsed on the bed in ecstasy.
I rose and sat down beside him, reaching for my drink on the nightstand. After sipping my drink for a bit, I glanced at the clock and said, "Oh dear, it's the witching hour Tom. You've been a lovely date, and I love the taste of your cock, but I must be going. Perhaps we can do this again sometime. Anyway, I hope so." I stood, retrieved my purse, and turned to leave. Tom was still lying on his back on the bed, exhausted.
"Why are you leaving so soon Ella? It's only a little after 11." He started to get up, but I motioned for him to stay on the bed. "Oh god, best blow job I've ever had, and she wants to run off. Damn!" he said, sounding very disappointed.
"I just have to leave Tom," I said, smiling at him. "You wouldn't want my carriage to turn into a pumpkin, now would you." I opened the door, turned to say goodbye, and left. As I walked down the hall to the elevator, very pleased with my performance, my mind began wandering back to how all this actually came about, how it started really. It was four weeks ago today.
Ah yes, four weeks ago, I thought, as I recalled the events back then. I was sitting in the nearly deserted bar, at midnight, alone and lonely again. Hanna, the bartender at the Blue Moon, came over to offer me another glass of beer. "No thanks, Hanna, I've had enough," I said as I nursed the last bit of beer from my glass, sighed heavily, and started to leave.
"Wait a minute Hal," Hanna said from behind the bar. "Why the long face all the time? You've been down in the dumps for months now. What's wrong?"
"Well, jeez, Hanna," I replied wearily, "look at me. Scrawny, short, balding before I'm even 30. I'm unattractive as hell, and I have no sex life, no social life, no friends. Nobody wants to be around a skinny, homely wimp like me. To make matters worse, I think I'm gay, but you have to be cute or macho to have gay friends. All I get to do is watch gay porno videos night after night. I don't have any hope at all."
"Your problem, Hal," Hanna said sympathetically, "is that you're the wrong gender. Skinny and short is good if you're a female, so maybe that's what you should be."
"Ha!" I retorted. "How the hell would I do that?" I looked at her incredulously, not believing what she had said.
"Well, I happen to know someone who could help. If you're really gay, you could become a woman whenever you wanted to, making it easier to pick up men." Hanna stared at me for a bit, gauging my reaction. "You know the beauty salon at Harbor Square Mall? Well, my friend Mary runs it, and she has a private room in the back where she does transformations sometimes. I could set up a visit for you, if you'd like."
"What's a transformation Hanna?" I looked at her, somewhat confused. "And why would I want to become a woman anyway?"
"Hal, look at it this way." She said, smiling a bit, or was it a smirk. I didn't know for sure. "If you're too homely to attract gay men, become a feminine, attractive woman and pick up straight men. There's a lot of `em out there aching for the blow job they never get from their wives, believe me. Any hotel bar on a weeknight is an all you can eat buffet of horny businessmen. All you have to do is look pretty and you'll get all the sex you want. A transformation, since you asked, is a make over of sorts, where Mary turns men into women temporarily. Or sometimes permanently I guess."
"Hmmm, I dunno Hanna, sounds kind of kinky to me." I lowered my head onto my arms, which were resting on the bar, bemoaning the state I was in. "I mean, I don't look good enough to be a woman. I'd just look silly."
"Silly? No Hal. Actually, I think it'll make you feel a lot better about yourself." Hanna stroked the back of my head a bit, feeling my pain. We'd been good friends for several years. "Let me make an appointment for you with Mary, to get the full treatment, in private. She even has a rear entrance, so nobody will see you go in. Okay?" She looked at me as I nodded yes. I was so desperate I was willing to try anything. "Alright, I'll call you tomorrow with the details. And trust me, I know you're going to love being a woman." She gave me a smile, then leaned across the bar and hugged me.
After getting the time of the appointment from Hanna, I set out to go shopping, with a list Mary had dictated to her. I had to purchase some women's lingerie items, shoes, and so on. Mary would provide a wig and dress for the first time, and after that I'd need to buy my own. While it wasn't easy buying that stuff, somewhat humiliating actually, I finally got it done. I hoped I'd bought the right sizes, which I had to guess at. It wasn't possible to try things on anyway.
I arrived at Mary's salon at the appointed time, 6 pm, went around to the back, and knocked on the door. An attractive, 50ish woman answered. "You must be Hal, so come right in. I have everything ready for you. The salon is closed now, so we're alone." She stood back and I entered a brightly lit room with mirrors everywhere, a large sink, chairs, and counters covered with cosmetics, brushes, and a myriad of items I didn't recognize. "Have a seat in this chair, Hal," she said, in a very warm and friendly manner. "You're going to enjoy yourself tonight dear, so just relax. And don't be modest, okay? For this to work we'll need to be real open with each other."
I set the bag with my purchased items on the counter, and sat in the chair. She had me take off my shoes and socks, and shirt and pants, but I left my shorts on for the time being. She started by washing my face and upper body, then shaved off the few chest hairs I had, as well as a small amount of facial hair. Leaning over me, she plucked my eyebrows into a feminine shape. That hurt a bit. Then, she handed me a razor and had me shave my legs. Finally, she applied a moisturizer all over me, to soften my skin, she said. I liked the feel of my smooth, shaved legs, as she rubbed some moisturizer on them.
Studying my face, she chose a shade of foundation and applied a light coat. "You really don't need much foundation," she said as she worked, applying powder with a large brush. "You actually have a lovely complexion." Next, she highlighted my eyebrows with a light brown pencil, then underlined my eyes. Black liquid eyeliner was next, above my eyelashes, followed by several coats of lengthening mascara. Finally, she brushed on a small amount of blush, for a highlight, and then applied lipstick. My face, always skinny and wimpy looking, now took on a decidedly feminine look. I was beginning to like it. When I wasn't looking Mary sprayed me lightly with a wonderfully feminine perfume called "A Little Sexy." I loved it, and Mary thought the perfume's name was appropriate for the occasion.
"Well now," she said, stepping back to admire her work, "that looks better. I see now exactly what Hanna saw in you. A female face, covered up by low self-esteem. I think this is going to work just fine. Let's get out your lingerie." She rummaged through my shopping bag, producing a black garter, panties, bra, half slip, stockings and high heeled shoes. "Nice," she said, smiling, "you did well. These are exactly what you'll need. Now, take off your shorts so we can get you dressed for the first time." Burying my modesty, I took them off, blushing with embarrassment.
As I stood there naked, Mary attached the garter around my waist, pointing out that my female waist was somewhat higher than my male waist. I sat and pulled on the stockings, hooking them to the garter snaps, per Mary's instructions, followed by panties and bra. Mary produced a pair of very realistic silicon breast forms, saying her salon sold them, as well as wigs and perhaps other items I might like. Their weight surprised me. After putting on the slip, I added my new black patent high heels and stood up. And nearly fell down immediately. The 3 inch heels changed the angle considerably. Mary said I'd get used to them soon enough. I had to admit I was getting pretty turned on at this point, wearing lacy lingerie, stockings and high heels. It was a very different kind of feeling though.
She went to a rack of clothing in the back of the room, producing a long sleeve black dress for me to try on. It fit nicely, so she pulled a brand new blond wig from a box and placed it on my head, checking for fit, and for how well the style went with my face. It seemed to be the right choice, so she styled it a bit with a brush, then allowed me to turn around and look at myself in the mirror. Wow! I was a woman, a really attractive woman at that. Amazing what some makeup and a wig can do. I just stared at myself in the mirror. As I did, Mary attached a gold necklace around my neck, and added matching clip-on earrings. I had to admit I looked stunningly beautiful. The ugly duckling had become the beautiful swan. Now I was really getting hot.
"What's your female name?" Mary asked, as I admired myself in the mirror. "You need a woman's name if you're going out in public."
So taken by my image in the mirror, I barely comprehended what she was saying. "What? Oh, my name? Hmmm, I'm not sure," I said, without taking my eyes off my image.
Mary said, "Well, since you're reenacting the Cinderella story, how about Ella?" As my gaze moved over to Mary's image in the mirror, she smiled, and I beamed with delight as our eyes met.
"Ella's perfect Mary. Thanks so much," I said. Just then there was a knock at the rear door. Panicked, I said, "I thought we were alone. You said,"
"Relax," Mary interrupted, "that must be your date for the evening. Hanna arranged it." She walked over and opened the door. There stood a tall, handsome man of about 30. A hunk, if you will. Whoa, I thought, a date for me? Mary invited the hunk in, and waved in my direction. "This is Ella, and you are?"
"Aaron," he said with a nice smile, "and I'm supposed to take the pretty young lady out on a date." He crossed the room and took my hand lightly in his. "Nice to meet you Ella. Hanna has told me about you, and I'm really pleased to be here. You look absolutely lovely."
I lightly shook his hand, saying, "Thank you, I'm pleased as well. What will we do on our date?"
Mary chimed in at that point, saying, "There's a nice little club with live jazz just two doors down. You two could go there for the evening." She handed me my shopping bag, now full of my male clothes, and gestured toward the door, urging me to go. As I started toward the door she handed me a black patent purse, saying my car keys and wallet were inside. She said I could settle the bill the next day, when I returned the dress. She had really thought of everything.
Aaron and I went out to the parking lot, where I dropped my bag full of clothes in my car, and then it was off to the club. Walking was still difficult in the heels, but we walked slowly and I managed okay, although I was really nervous. Inside the club we found a small table off to the side and sat down. A jazz trio was playing a soft number, allowing us to talk. Over several drinks we talked and laughed, and several guys asked me to dance, but I said no. Aaron flirted with me all evening, getting me really hot. What a dreamboat Hanna had gotten for me, exactly the sort of guy I stood zero chance of landing as a male. But as a female I was really attracted to him, and, I think, he was attracted to me. Hanna was absolutely right when she said I'd love being a woman. I was having the time of my life, giddy with excitement, and aroused at the prospect of an evening with Aaron.
As the evening came to an end, we walked back to our cars, but I was a little unsteady from the drinks I'd had. Aaron suggested, no, insisted actually, that he would drive me home. I could retrieve my car in the morning. When we arrived at my place I invited him in for a nightcap, which he readily accepted. I made us a couple of light drinks, and we snuggled up together on the couch. He put his arm around me and kissed me several times, saying how beautiful I looked, how much he liked my perfume, how turned on he was by me. I was really getting pretty hot by this time, wondering if I should make a move, when he moved first.
"Hanna tells me you're really inexperienced with sex Ella," he said softly, "so I was hoping we'd have a chance to be alone. I think you need to explore your feminine desires tonight, while you're feeling like a woman. Hanna wanted me to help you with that, if you'd like me to."
"Oh yes Aaron," I said softly, "I just want to be a woman tonight, and satisfy my man. I hope I'm not too nervous." I moved my hand down to his knee, then to the inside of his leg. "What would you like me to do?"
"Put your hand on my crotch Ella, and feel my cock. Hanna says you've never done it before, and that you need to experience it." Nervously I moved my hand up to his crotch, wrapped my fingers around his erection and felt it through the fabric of his pants. "Hmmm, yes, that's it. Do you like it?" I nodded a yes. "Good, now unbuckle my belt, and unzip my pants baby." I did as he asked. "Now slip your hand in my pants and just stroke it until it starts to get really hard." I began massaging his hardening cock with my hand. I really liked how his erection was responding to my touch. It felt a bit weird though, as I had never touched another man's cock before. It was now becoming a rock hard, throbbing erection. "Ummm, Ella, nice, really nice baby. Now slip off my pants and get on your knees. You've got me really hot for you now."
My desire for Aaron was raging as I slipped his pants and shorts off, then slid down to my knees. I was pretty uninhibited at this point, from the alcohol I guess. I found myself staring at his rigid erection, only inches from my face. "Do you want to kiss it Ella?" he asked. He was really being sweet about this. I looked up at him and nodded again, but I was really scared about what I was about to do. "It's okay," he said softly, "kiss it if you want to."
Slowly I leaned down, closer to his beautiful erection. I was fascinated by it, and slowly, gently, wrapped my hand around it. I could feel the muscles stretched taut, as it became more swollen. I was really nervous now, afraid of what was ahead. Finally, though, I couldn't resist, and I kissed it briefly. I liked it, so I kissed it again, this time lingering on the head, my tongue licking it. I was really surprised at the smooth skin, almost like satin, I thought. I caressed it with my tongue, slowly working my way down his shaft, enjoying his manhood. Aaron said "It's okay Ella, take it slow, and don't do anything you're not comfortable with." What a neat guy, I thought. My fantasy for several years now was to do just what I was doing, although I hadn't figured on being dressed as a woman. "We're reaching the point of no return Ella," he said. "If you go much further I won't let you stop, so be sure this is what you want to do."
I gazed up at him and nodded yes, that I wanted to continue. "Okay Ella," he said softly, "take it in your mouth baby, as deep as you want." I slowly took his cock into my mouth. Hmmm, I thought, what a nice taste. I slid my mouth down his shaft a bit, licking it with my tongue and lightly sucking it. "Do you like it Ella?" Aaron asked softly. I pulled it out and sat up briefly.
"Yes," I said, breathlessly, "I love it so. I want you to teach me how to do it. Teach me what turns men on, and how to get them to come in my mouth. I want you to come in my mouth tonight Aaron, so I'll lose my virginity. Please."
With that I again took his erection in my mouth, sliding down the shaft as far as I could go without gagging. ""Slowly move down, then up Ella," he said. "Use your tongue to caress it, and swirl around it. Caress my balls with your hand." He moaned a bit as I responded to his words. My rhythmic up and down sucking got a little faster as I got more excited, and I tried taking him deeper into my throat. I found if I tilted my head back a bit it opened up my throat, allowing me to fill it with his rigid, throbbing cock. To better achieve this, I pulled him to his feet, allowing my head to tilt back more. More.
Now he stood before me, plunging his rock hard cock into me, as I sucked voraciously. I was so hungry for him I couldn't get him far enough into me. Aaron sensed my need, and placed his hands on the back of my head, pulling me into him as he thrust his member into me, deeper and deeper. It was wonderful, better than I could have imagined. I loved having his cock in my mouth, fulfilling my dream. He was plunging faster now, his hips moving in time with me, as I sucked him closer and closer to what I hoped would be a huge climax.
He started to shudder, moaning and gasping in sheer pleasure. "Oh yes baby, yes," he moaned passionately, "that feels so good." I sensed he was about to climax, and I instinctively tried to pull my mouth away, even though I really wanted him to come in me. He held my head tightly in place, not allowing me to pull off. I was in a state of panic, trying to pull away, and afraid of what was going to happen. My desperate fear was taking over, ruining my pleasure. He was plunging deep into my throat, his hands pushing tightly on the back of my head. "Oh yes Ella, yes baby, it's so good," he moaned loudly as he reached a massive climax. His come spurted into my mouth in a tremendous explosion, blast after blast, and his grip on my head tightened, as I gagged briefly and struggled to swallow it all.
As I got over the shock of how hard he came I found he tasted surprisingly delicious, and I couldn't get enough of him. He plunged his swollen cock deep into me again, as another spurt exploded into the back of my throat, his grip on my head tighter still, with my face buried in his pubic hairs. He shuddered, letting out a moan of intense pleasure. Wow, I thought, what a climax. I loved every second of it, and wondered why I had been so afraid. Finally, he released my head and I cleaned him up as much as I could with my lips and tongue. He slowly withdrew his cock, stroking the back of my head softly. "Oh Aaron, that was wonderful." I said breathlessly, looking up at him. "I hope you'll let me do that again."
"Again?" he said, smiling, taking my hand to help me to my feet. "We can do this as often as you like. You were fantastic Ella, just the best. Wow! I'm sorry I had to hold your head so tight, but I wasn't going to let you quit after you'd come so far." I told him I was glad he held me tight, as I really wanted him to come in my mouth. I was just scared, and didn't know what was going to happen. I promised him he'd never have to hold my head like that again. We cuddled on the couch and finished our drinks. Aaron wrote his phone number down for me, and made me promise to call when I wanted to see him. He also said I needed to take some time practicing dressing as a woman, and just being a woman. My voice needed work, and I needed to learn makeup skills, not to mention acquiring a full wardrobe. A lot to do indeed, so I told him I'd call in a week or so, which pleased him. He gave me a long goodnight kiss and left.
The next day I returned the dress and jewelry to Mary and settled my bill for the transformation, wig and breast forms. It was expensive but worth every penny. I was dressed in male attire and hated it. I couldn't wait to be a woman again, and told Mary what I was feeling. She wasn't a bit surprised. She gave me a list of cosmetics to purchase, and we made an appointment for the following day, so she could give me instructions on how to apply them. She also gave me a long list of retail businesses and web sites where I could buy clothing, shoes, jewelry, and other accessories. She recommended I get my ears pierced right away, which I did that day.
So, I went shopping, first at the mall and finally on the internet, finding a huge assortment of items, many of which I bought. I found myself wishing I could go shopping as a woman, but that would come soon enough. I found a web site that explained how to make cleavage, which I tried successfully. I was having a ball, even if I was rapidly draining my savings account. I didn't care. After my cosmetics lesson from Mary, I began dressing as a woman every night after work, practicing makeup, voice, walking, gestures, and everything else feminine. Hanna was right, I felt so much better about myself when I was a woman, like it was meant to be. I was having a blast.
After a week of that I called Aaron, and he agreed to take me out. I wore a rose colored silk blouse and black knit skirt, 3 inch black patent heels, and coordinated jewelry. I looked great, and completely feminine. He took me to the Blue Moon Lounge, so Hanna could see me. She loved the complete transformation, from mousy little wimp to beautiful woman, and hugged me with joy. I thanked her over and over for talking me into it, and told her she was right about it making me feel so much better. After a couple of drinks Aaron took me home, where I gave him a great blow job, eagerly swallowing his come as he gently held the back of my head, his cock buried deep in my throat. I loved every bit of it.
Over the next three weeks I saw Aaron several times, and I got better and better at my feminine presentation, and at sucking his cock. We went out to different clubs, acting like two lovers, walking hand in hand, making out in public. One night we tried a new position, with me lying on the floor on my back, and Aaron on top, fucking my face. We both really loved it. Finally, after about 4 weeks, he said I had become so good it was time to try going out on my own. He wanted me to taste another man's cock. I shivered with excitement, but sorry that Aaron wouldn't be going with me. Sulking a bit, I turned to the internet for solace, and found a web site for a women's clothing store called Crossing Pointe. They were having a going out of business sale. I found a red slinky knit dress in my size, on sale for $9.95! What a ridiculous price, I thought, as I ordered it. The overnight shipping cost more than the dress. When it arrived I tried it on, finding that it fit perfectly, and looked so sexy. It was really low cut, allowing for a lot of cleavage. My first venture out alone would be that night, wearing a low cut, sexy red dress. I couldn't wait.
Leaving Tom's hotel room, after giving him a great blow job, my first with anyone other than Aaron, I approached the elevator. Pushing the button for the lobby, I thought about returning to the bar to see if anyone would be interested in a little late night tryst. Just as the elevator went "bing" a voice called to me from down the hall. "Ella, wait." It was Tom, hustling down the hall, trying to zip up his pants. "Listen," he said as he approached, "I've waited all my life to meet someone like you, and I don't want you to get away so easily."
"Oh Tom," I said, a little perturbed, "I'm really sorry, but I just have to go." I didn't want him getting any ideas about undressing me and finding out the truth. "Maybe I'll come back tomorrow night, and if you're in the bar, well, maybe we could get together again. Okay?" With that, I stepped into the elevator. As the door closed Tom said, "Tomorrow night, I'll be there." I smiled at him just before the door was fully closed.
Walking through the hotel lobby I decided to return to the bar and check out the scene. As before, my red dress garnered a lot of attention for me, and I loved it. Sitting at a small table I ordered a drink, and settled back to see what might happen. Soon enough, a gentleman of about 50 approached, asking if he could join me. I nodded, and he sat down. A bit of small talk, some leg rubbing, and we were in his room in no time. I was definitely getting the hang of it.
As he began kissing me hungrily, my hand slid down to his cock, massaging it through his pants. He said, "Oh baby, I really want to have you now." I tilted my head up a bit and smiled at him, as I continued rubbing his bulging erection.
"Tonight, unfortunately, is my time of the month," I said, looking up at him. I was learning fast. "But what I'm wanting to do you'll like even better, big guy." With that I kissed him passionately, then unbuckled his pants and, dropping to my knees, pulled them off, revealing the biggest cock I'd ever seen. "Wow, you're really hung," I blurted out. "I can't wait to get that in my mouth." With that I began kissing his huge, swollen member, licking a small amount of come from the head. Grasping his enormous erection in my hand, I took it in my mouth, sliding my lips down as far as I could go. My mouth was stretched to the limit as I sucked in and out, swirling my tongue as I withdrew each time.
He was getting pretty hot already, pumping his cock into me as I sucked down the shaft. "Oh baby, I love that. More baby, that feels so good," he said breathlessly. I wrapped my arms around his hips, pulling him into me, as I felt his hands on the back of my neck. Pumping and sucking, he gasped and groaned with passion, as I took him deep into my throat, my head bobbing up and down on his throbbing member. His hips pumped in and out rhythmically, thrusting his swollen member deep into my mouth time and again. I was in heaven, gripping his hips and pulling him into me. He let out a passionate moan, saying, "Oh baby, I'm going to come right now," and then exploded deep in my throat, as he continued pumping in and out. His seed came in a torrent of spurts, seemingly endlessly, as I eagerly swallowed it all. He tasted wonderful, and I was hoping he'd never stop coming. Finally, I licked him clean, and he helped me up on my feet.
"Oh sweet baby," he said, "that was the best I've ever had. Where have you been all my life?" He gave me a big hug, and then kissed me passionately.
I smiled, sat on the bed, and took a couple of long sips from my drink. He sat down next to me, as if he wasn't done, but I was. "Oh, look at the time," I said. "Gotta go. Thanks for a lovely time. Maybe we can do it again sometime. But my mouth is going to hurt for a week, after sucking that huge cock of yours." With that I giggled and smiled, then got up, straightened my dress, and left. The red dress strikes again, I thought, smiling, as I made my way to the elevator. Not bad, all in all, sucking two cocks in one night. My success had led me to a decision this evening. It'll take some doing, but I think it'll be worth it. From now on, I'll be living as a woman full time. I thought I should go by the Blue Moon and tell Hanna. She would be thrilled, I was sure.
The next night, I met Tom in the bar, and really sucked him dry this time, as I pulled him down to the floor on top of me, and let him fuck me in the mouth. He really loved that, climaxing harder and more passionately than the previous night. My "time of the month" excuse worked perfectly, just as before. Tom begged to see me again, so I gave him my e-mail address, telling him to let me know when he'll be in town next. He'll have a difficult time going back to his wife, I thought. Leaving Tom's room, I smiled and giggled a bit, wondering if it was possible to suck a thousand cocks in a year. Hmmm, I chuckled, as a smile came over my face, on my knees, or on my back, either way I loved it.