April's Adventures, Continued The tale of a man's experiences as a woman By: Sebastian
Copyright 2003-2004 by Sebastian (All rights reserved)
This is a "mostly" true story about a man's introduction into cross-dressing and sex as a woman, as well as sex with groups of consenting adults some of them the same gender. If this offends you, you are under 18 or it is illegal in your country, please close the file and leave now. Otherwise, read on and enjoy!
Chapter Two: April's Dawn
Well, it had been three whole months since Betty had first caught me wearing her sexy under things and playing with her dildos and vibrators, three months since we had had our first encounter with Brian, three months of getting to know Betty better than I have in all of our five years together. Learning her secret likes and dislikes in ways I had never imagined. I had always thought that I knew what she liked and didn't, but I hadn't a clue before. Our relationship hasn't been hurt in the least by our sexual adventures. Instead we have grown closer and our love has grown.
We have had the opportunity to repeat our sexual encounters with tenants in her complex three more times. One of these was even a couple, that was the one time I was almost found out (but lets save that for another story). I am often in the office with her and am introduced as April from the home office. None of the other agents has guessed that the guy that Betty goes to breakfast with in the morning is the same April that helps her rent to that difficult couple in apartment 3C. I will sometimes hang around the office, or go to lunch with the girls. It is such a turn on when we all go somewhere for lunch and all freshen up in the lady's room together. To everyone in the office I am just one of the girls.
Several times I have run into Brian while walking around the complex, as April. We stop and chat and have even kissed and it excites me to know that I can give him an instant hard-on if I even remotely refer to our first meeting. I have even met him when I am just Betty's boyfriend and was even invited over to have a couple of beers and watch the game. He even bragged to me about the women that had done him the night he had rented his apartment. I told him he was full of shit, and so he described, in precise detail, what had happened that night. He was pretty accurate except when he added the fact that he had fucked all three of us. I for one knew he hadn't, I know I would have remembered that!
About a month after that first night Betty was offered the managers position at her complex. It included a three bedroom garden unit free. We moved into one that she picked just for us. With all utilities and rent included we were able to afford to get rid of all our old stuff and furnish the apartment with furniture that fit our lifestyle. It was a really luxury unit when we got done. We turned one of the three bedrooms into a home office for me, and the other into a bedroom for Lorie to use whenever she wanted to spend the night.
It is a good thing that the unit has three closets because the girls are always going shopping and buying me clothes and things. The closet in my office is quite full of my sexy things. On the rare occasion that a client makes some comment about them, I just grumble about Betty taking up all the closet space. The girls has even taken me along when the go shopping, often picking out clothes for me to try on, and even coming into the dressing room to help me try them on.
I was sitting at my desk one morning, in my regular morning attire of a pair of soft panties and a chemise, when Betty calls. She has set up an appointment to show one of the super-luxury garden units to a very wealthy Asian client and is sure that I should be there for this one. She told me to what she wanted me to ware for the meeting; a pair of white lace stockings with a white lace garter belt, my red silk panties with white lace trim, and the matching bra; and a white silk chemise. I was to wear my red wrap-around skirt and matching silk blouse and white heels as well. She said she would send Lorie down to help me in a few minutes.
I stripped and jumped in the shower and used my hair remover gel to take care of any stray hairs. I did my cock, balls, and ass and was just soaping up when the shower door opened and there stood Lorie. She was naked and started checking me over to make sure I was ready. She was on her knees, checking on my ass, when she said that I had missed a spot. She jumped up and got the enema bottle and filled it up with warm water and washed my ass from the inside. After a dump and two more bottles of water and two more dumps. We scrubbed up and she checked my asshole and pronounced me ready. I turned around and stuck my hard little cock in her face and said damn right I am. She gave it a kiss and said that Betty told her not to make me cum because I was going to need all of my strength later.
After our shower it took another hour to finish my transformation into April. Damn I looked good as we walked up to the office and went into Betty's private office. She was sitting behind her desk, with her legs crossed, showing a lot of leg. There was a stunningly beautiful Asian women sitting across from Betty. I was introduced to her and learned her name was Dawn. She was about 4 foot 8 or 9 and weighed maybe 90 pounds. Her hair was a glossy black and worn short, barely touching her neck. Her face looked like porcelain, so white and smooth, almost breakable. I was trying to place her nationally, and decided that she had to be `Thai'. She was wearing an emerald green skirt and matching silk blouse. Her eyes were almost the same shade of green and they were almost hypnotizing. Everything about her said petite, wealthy, and sexy!
We all walked to the section of the property where the owners had built 4 very secluded, very luxurious, and very expensive units. They were fenced on three sides and landscaped so that they had very private back yards, which was necessary since the back wall of the bathroom was a glass door that opened into the backyard. There was a hot tub on the patio right outside the bath. It was a phenomenal place, very sexy, and very expensive! As we were walking through the apartment Betty and Lorie drifted off and by the time Dawn and I had reached the bathroom area we were alone. She was so delicate and was wearing some perfume that smelled like hot and spicy flowers. It was very erotic. The bathroom was the clincher. If I had had a contract there she would have signed it on the spot. Dawn was fussing all around the room inspecting everything.
Dawn saw Betty and Lorie standing in the back yard and ran out to tell them that she loved it and would take it. They were talking about how sexy the bathroom was. Betty remarked that you could take a shower and walk outside to air dry in the sun and never have to worry about being spied upon. Betty and Dawn were walking around the yard, arm in arm, talking about what Dawn needed to do next. Betty's hand was slowly sliding down to Dawn's ass. In no time at all they were embracing and Dawn had her face in Betty's breasts. She was unbuttoning Betty's blouse and since Betty was braless in seconds she had a nipple in her mouth. Betty responded my reaching around her and lifting her skirt and sliding her hand in Dawn's panties. She had a perfectly shaped ass, and I do mean perfect. Her ass was pear shaped with tight cheeks, and a well-defined crack. It was begging to be licked, and that is just what I was going to do.
I stood behind Dawn and began stroking her sweet ass. I slid my hand into her panties next to Betty's and began fingering Dawn's asshole. She groaned and thrust her ass back and my finger slid in to the second knuckle. Dawn released Betty's breasts and reached back and spread her ass wide and said "more please." I thought she meant faster or harder so I did both. She started thrusting harder and said "No, more fingers, I want it bigger". I was more than happy to oblige this hot Asian beauty.
Betty and Lori had stepped to the door and were waving goodbye as they went into the apartment. I thought they were teasing me until I heard the front door close. I almost panicked and ran after them, but Dawn was so fucking hot and drop dead sexy I didn't care if I got caught. I just wanted to see more of this woman. I took Dawn by the hand and led her to a lounge next to the hot tub and proceeded to undress her. When I had her blouse off and her bra unhooked I knelt and took her boyish little titties in my hands and ran my thumbs over the nipples. She trembled and pressed them harder into my hands. From where she was sitting I was sure that she couldn't see my cock sticking straight out making a tent in my panties and parting the opening in my skirt.
As I lowered my mouth to her breasts and took a nipple in my mouth she is starting to unbutton my blouse. I know I am going to get busted at any moment but I didn't care I had to see all of her. I slowed her down by reaching behind her and started unbuttoning the buttons on her skirt. I and fumbling around and can't quite get them all undone. Dawn stops unbuttoning my blouse and roles over on her stomach and let's me undo her skirt. As I started to tug it down her ass she raised up enough so I could get it off of her. I had her almost naked, only the white stockings and panties remained. I reached for her ass and she said that she wanted to be naked. I proceeded to take her stockings off her sexy legs, kissing that baby smooth skin as I went. I worked my way back up to her ass and started slipping her silk panties down her legs.
She raised her ass in the air and spread her cheeks and asked me to do her ass. I bent my face to her ass and began to kiss and probe her ass with my tongue. She was on all fours with her legs squeezed together, her head down on the lounge and her ass in the perfect position for licking or fucking. I reached under her and pinched her nipples as I fucked her ass with my tongue. It opened for me like a flower as she was groaning and thrusting her ass in my face. I wanted to taste her cunt before it was too late. I asked her to turn over and let me see her pussy. She slowly turned over, and as my eyes went to her bush, I got a real surprise it was his bush. I was shocked and immediately knew that Betty had set me up.
I wanted to get mad but I couldn't. Dawn was the perfect woman in every way, except for the cock. It wasn't a man that looked like a women (I'm that) it was a woman that happened to have a dick. I was going to get some of her/him no matter what. I knelt between her legs; that is the way I thought of Dawn as a woman, and began kissing her little cock. Like most Asian women she has very little pubic hair. Her cock was only about 2-3 inches long and about as big around as my thumb. I gently sucked it into my mouth and slid down till my nose was buried in her hair. I reached under her ass and felt for her balls. They were like two little marbles in a little bag. I changes position downward and was able to take them; and her cock in my mouth. I was a wonderful feeling to be able to do this. I started chewing very softly and licking at the same time. I had her humping up and down in my mouth trying to fuck my face. I slipped those two fingers in her ass again and she rode them like crazy. Dawn was moaning and fucking her ass on my fingers and her cock was throbbing in my mouth and I knew she was about to cum. I let her cock slip from my lips and shifted my position between her legs. I took just her balls in my mouth and continued to lick and suck them. I was rewarded for my efforts as she started to cum. Her little cock was pointing up in the air and shooting gobs of spunk up in the air. I could feel her balls contract in my mouth with each shot. I gathered as much as I could and was rubbing it into her soft skin. For such a little cock she sure shot a just of cum in just a few seconds. I had to let her balls slip out so I could watch.
I pulled my fingers from her ass and began caress her hips and tits, as I would any woman after sex. I eased up next to her and slid onto the lounge and lay next to her. She had tears in her eyes and she was silently crying. I told her everything was ok. That she was beautiful and sexy and I had really enjoyed what we had just done. She said that she wasn't upset, that they were tears of joy. She started gently kissing me and reached for the buttons of my blouse. She said "Now let me do the same for you." Little did she know that it was really going to be the same thing? She eased off the lounge and had me lay on my back as she knelt by my side and began to undress me. She started with the buttons of my blouse and after she had them undone and my blouse laid back she went to work on the ties of my wrap-around skirt. I was prepared for her to be upset when the inevitable happened and she saw my cock sticking out of my panties.
Dawn opened my skirt and I watched, and waited as she looked down at the tent my cock was making in my panties. I was so turned on that the pre-cum had soaked them and you could see the head of my cock through the red silk. At first she just stared, and then she slowly slid her hand into the waistband and wrapped her delicate fingers around my cock. She said, "You poor girl, you have the same problem I did. Let me help you with that." I just said, "Please," and let her have her way with me.
I don't look feminine when I am undressed like Dawn does. She is a woman who just has the good fortune to have a dick. While I look like a guy who would like to have a pussy, oh well. She was making me feel very good as she explored my half dressed body. She didn't try to take my bra off and was squeezing my breasts through it with one hand as she stroked my cock through my panties with the other. Her delicate mouth tracing little trails on my stomach as she gave me little love bites all over. She worked her way down my body and then started to make love to my cock through my panties. I mean she didn't just suck my hard cock. She made love to it. Aside from the fact that I was horny as hell; and that she was so damn beautiful and that we were outside in the garden, and all the rest. I would do anything to have had others do to my cock what she was doing to me. It wasn't one thing, it was everything, every movement, every caress was so sensuous and loving and so sexy. I could have taken her attentions for hours.
I was slowly starting to thrust my hips in time with her movements. She had slipped a hand under my ass and was working a finger into my ass. As I thrust back and forth in her mouth I was fucking my ass on her finger. I got harder with each thrust. I reached for Dawn and she turned so I could reach her ass and cock. I began gently stroking the insides of her thighs, and that little spot between her balls and ass. She responded with a moan and moved so that I could slip a finger in her ass again. She started humping my hand and I slipped another finger in there and she moaned and ground her ass on my hand.
Suddenly, she stopped everything and stood up and went inside. I thought what was wrong. She came back and proceeded to put a condom on my cock. Then she stepped up on the lounge chair. She was facing my head and I thought she was going to stick that cock in my face but no. While still facing me she started to squat down on my cock. I didn't believe that I would be able to fuck her ass from this angle but she aligned the head of my cock with her ass and sank down. As I went in, her cock puffed out. In no time she had me fully buried in her ass. It felt so good to be inside her. I was buried to the hilt and her cock was against my belly. I reached down and started to stroke her cock as she began riding mine. The feel of her balls rubbing that soft spot at the base of my dick, every time she came down was indescribable.
Her cock was too small to really jerk-off in the standard sense, so I took my hand and pressed it against my stomach. This caused Dawn to change from bouncing up and down on my cock, to rocking her hip's back and forth. She was dragging her cock and balls against my hand as she fucked it. I was playing with her little breasts with my other hand and time seemed to stop. We may have been at it for seconds or minutes or an hour, I couldn't tell. All I knew was that Dawn was making me feel incredible and that I wanted this to go on forever. However, that was not to be. With the thrusting action, Dawn's ass was providing way to intense a feeling along the shaft of my cock. I felt the rush of my load as it rushed up the length of my dick. I grabbed Dawn by the hips and held her tight as I pumped my load in her ass. She began squeezing my cock with her ass and milking me dry.
She leaned forward and kissed me. This trapped her dick between our bellies. Was we kissed and held each other she gave a little cry and began to shoot her load. My dick was slipping out of her ass as she continued cumming. The slippery feel of her cum as she rubbed against me, I could feel her cock pulse and jet the thick juice between us. I held her ass and pulled her hard against me and we held each other as we began to slow down and return from the intense level of excitement we had just had.
We stayed there holding each other for a long time. She was still laying on me with her head on my shoulder. It felt so natural for her to be there like that, and it was a very comfortable position, she was light as a feather. I was rubbing the small of her back and kissing her neck when I felt how warm her skin was getting. I then noticed that the sun had moved and we were probably getting a, serious case of, sunburn, or rather she was, since she was my umbrella. Dawn had begun to doze and as I shifted my hands to her sides she woke and said "Thank you April that was wonderful." I told her that we had better move out of the sun and she rolled off me. I stood and picked her up in my arms and carried her to the shower to clean up.
She finished taking my clothes off and we explored each others body as we let the water rinse the remains of our lovemaking off our skin. It was very sensual and exciting but neither of us was physically responding. When we finished we remembered that there were no towels, so we just walked back outside and moved the lounge chair under the tree and lay down on it together and let the warm air dry us. We drifted off to sleep in each other's arms in peaceful contentment.
I awoke to the feel of someone kissing my cheek. I opened my eyes and there was Betty standing over us. She was smiling and I just looked up and mouthed thank you to her. She nodded her head and looked at her watch. I could tell from the position of the sun that it was late afternoon but when Betty showed me her watch I was shocked to see that it was after 5 pm and that we had been at it for 6 hours. We awoke Dawn and the three of us gathered the clothes that were scattered in the yard, bathroom, and elsewhere. Betty helped us both get dressed and restore our makeup. As we left the apartment Dawn kissed me deeply and than did the same to Betty. I saw Betty's nipples harden and knew that they would be together soon as well. I needed to go home and recover so with a parting caress I left my Dawn to return to the office with Betty.