I suppose a little background is in order here. I live in a small, fairly cut-off, and conservative, suburban community. I have been a closet crossdresser for twelve of my twenty-one years. And, as far as I know, no one knows about my desire to dress as a woman; until now, anyway.
My hair is naturally long, a hold over from my heavy metal days. A few months ago, as I became more at ease with my dressing, I finally picked a name for myself: Melissa. I began to keep my legs shaved and to wear women's panties under my "normal" attire. Occasionally, I'll even wear thigh-highs or pantyhose.
I had been working in a restaurant over the summer, mostly doing miscellaneous work in the kitchen. I had worked there the summer before, so I knew most of the staff. There was, however, a new waitress named Amy. She was a fairly attractive asian girl, twenty years old, but highly mature (I always thought she was in her mid twenties). We got along great, always cracking jokes and sharing cigarettes. She had told me that she had a boyfriend, so I never considered her as anything more than a friend...until one night.
We had both gotten off of work early. I had access to the restaurant's beer closet so we decided to just hang out and drink a few beers and smoke a few cigarettes. We had never really had a real conversation before and soon found ourselves engrossed in an interesting one. Out of nowhere she says to me very casually, "I don't know if you are aware of it, but I'm bisexual." This was the first time anyone had come out to me. She began telling me about how she and her friend had decided to go to a bi/gay/lesbian/transexual ball together and had made out, but that circumstances had not yet allowed them to go any further. She also mentioned that not even her boyfriend was privy to this information.
The thought of her kissing another woman started to put a rise in my Levi's. I wanted to reciprocate and tell her about my crossdressing. I knew that I could trust her with my secret, but I was not yet totally comfortable with myself to come out to someone; but I started to make plans to.
In december she left her job at the restaurant, but not before attending the staff christmas party. I wanted to tell her my secret and even hinted that I had something to share with her. Before I could confide in her, however, her boyfriend showed up and the two of them left; but not before we exchanged phone numbers.
It took me a few weeks before deciding to call her and I am sooo glad I did. We spent a few minutes catching up before I asked her if she wanted to get together and knock back a few. That must have triggered her memory because she suddenly asked me what it was I had wanted to tell her. I asked for her email address and told her to check her inbox in about an hour. So we hung up and I got to work writing down the whole story. I knew she would be accepting so I didn't hold anything back. I told her how I had gotten started and how I had evolved, as well as the problems I was currently having shopping for myself.
She called me right after she read it. I could tell she was really excited and possibly a little turned on. She volunteered to help me with makeup and shopping for clothes. This was what I had hoped for. I asked her if she was free to go shopping in the next few days and, as luck would have it, her boyfriend was going to be out of town the following week. So we set everything up for our outing.
The following wednesday, she came to my house late in the afternoon, bringing everything I had asked her to: her makeup kit and some of her shoes and dresses of assorted sizes. Only stopping to grab a beer from the fridge, we got right to work. First I showed her my collection of women's clothing: a few tops, a skirt, some panties, a bra, garter belt, stockings, pantyhose, and, my favorite, black leather pumps with a 3 1/2" heel. After putting on my bra and inserting my mail order breast forms, I tried on the dresses to try and determine what dress size I could fit into; it ended up being the same as my skirt size, but it saved me having to play the guessing game. Next we tried out the shoes. The pair I owned were a little too big (a size 9), and I figured I was about a size 8, which I was.
That out of the way, we sat down and I pulled out the clothing catalogues I had and showed her what I would be looking for the next day. She admired my taste in clothing: very casual, yet slightly conservative. She was also amazed at my ability to co-ordinate outfits in my head without even seeing the garments.
Armed with the knowledge of the look I was going for, we proceeded to the bathroom to test out makeup. We went through everything she had brought, every possible color combination. After a few hours we had finally arrived at several color patterns that would work for me.
We cleaned up and went for a late dinner. When we got back to my place, we started drinking and talking. The more we drank, the more personal our conversation became. We soon found ourselves sharing our most secret and intimate desires. We both agreed that anal sex was great and she wasn't shocked when I shyly admitted that I occasionally liked to take a finger or a dildo up my ass.
She re-iterated her desire to make love to a woman and again told me about the time she had french kissed her friend. Jokingly I told her that the best I could do for her was a guy in women's clothing. We both laughed, but I saw something change in her eyes. Sticking with the lesbian theme of conversation, I asked her if she had ever seen a lesbian porno movie. When she said that she hadn't, I immediately went and popped one into my VCR.
The movie I had chosen started off with two women kissing, touching, sucking, and licking each other to orgasm. The next scene started off much the same way, until one of the women pulls out a strap-on dildo. Amy's mouth dropped open at the site of it.
"Is that a strap-on? I've never seen one before."
She was really getting off watching the two women fucking each other on the screen. I got up to get another beer when the scene was over and when I came back, I found her re-watching it, ogling at the site of the strap-on.
She stopped the tape before she could lose control and we talked about a neutral subject for awhile. But it wasn't long before the subject of strap-ons came up. She said that she would love to to have another woman make love to her with one, as long as she got to return the favor. I decided to tell her my most guarded fantasy: I wanted a woman, with a strap-on, to fuck me up the ass while I was dressed en femme. She just about orgasmed right there, she was definitely in to it.
So that night, unbeknownst to her, I added one more stop to my list: an adult store for a strap-on cock.
We got up early the next morning and drove to a mall about 40 minutes away. First we stopped at a drug store and picked up my makeup. Then we went to all the discount clothing stores. I found a few pairs of shoes at (of all places Payless), and a white cotton tank dress, a few skirts, two tops, and some pantyhose at some other stores. Next came the department stores, where I got a two piece outfit, skirt and blazer, on clearance, with a silk blouse to go with it, and a few bras and panties. Just for the fun of it, we decided to go by the Frederick's of Hollywood. I found a black satin and lace bustier with garters that had been marked down because their was a small white spot (unnoticeable) on the inside of one garter and someone had stolen the matching g-string; it was half off!
Neither one of us could wait to get back to my place; but first, I had to make a quick stop. I pulled up to a non-descript building and went in while Amy waited in the car. Inside, I bought a strap-on harness and a flanged seven-inch rubber dildo. When I came back, I put the bag in the trunk and drove home.
We arrived at my place mid afternoon. I had promised Amy that I would make her dinner. So after putting my new purchases away, she jumped in the shower while I started making supper: a mixed greens salad, sesame chicken with rice, a sorbet, and a bottle of champagne (you don't learn nothing working in a kitchen for two years).
While the chicken was cooking, I laid out my outfit for the evening. I had promised Amy that she would get to meet Melissa, and I wanted to look my best. I chose the forest green sweater and 13" velvet skirt that I had bought that day. Underneath I would wear my new bustier, black stockings, and lace panties. On my feet I was going to wear a pair of black 2" heels.
Amy and I traded places; she watched dinner while I took a shower. When I got out of the shower, I dried off, blow dried my hair, shaved, and put my hair back with a black velvet scrunchy. After setting the table, I put on my makeup: a light pink lipstick, violet eye shadow, and a little rouge on my cheeks. Before I could start to dress, the timer on the oven went off. I served dinner, lit the candles, opened the champagne, and then ran off to get dressed. I looked at myself in the mirror. The knowledge that I was about to appear before someone dressed en femme excited me so much that I had a raging hard-on poking through the front of my skirt. Worrying about getting pre-cum stains on my clothes, I put an unlubricated condom over my cock, and tried to steady my nerves.
When I came back, Amy was already seated and had poured two glasses of champagne. Her eyes lit up when she saw me and a smile spread across her face.
"Melissa, you are absolutely gorgeous," she said as she got up to greet me.
We sat down to dinner and instinctively I began to act like a woman (it helped that Amy kept calling Melissa). I sat very demurely and properly. I remembered all my manners, talked softly and sweetly. I could see that Amy was a little confused at times. She kept forgetting who Melissa really was.
After dinner we cleared the table and moved to the living room. I put on some soft classical music and we opened a bottle of wine. We sat on the couch talking. Anyone looking on would have seen two women engrossed in a gab session, Melissa was that real. I felt like a woman, the role just seemed to come that naturally to me. Amy was looking at me with a slightly wicked look in her eye. We had moved together fairly close together on the couch.
Amy suddenly got up and said, "Let's dance!"
I stood up, a little shakily as I was not yet used to my heels. Amy put her arm around my waist, I put an arm around her neck, and she took the lead. As we slow danced around the room, our bodies were getting closer and closer together. I rested my head on her shoulder. Eventually we got tired and collapsed on the couch again. We looked at each other, both flushed and smiling, and kissed. We exchanged a few light kisses at first, but soon we broke out into a long and passionate french kiss.
I let Amy be the aggressor. She pushed me back on the couch, never breaking our lip lock. I threw my arms around her neck, very ladylike. When our kiss finally broke, I gave her a wicked look and told her I had a present for her. I went and grabbed the bag I had received at the adult store earlier and returned to the living room. She was a little confused when she pulled out the dildo, but as soon as she saw the harness underneath, her eyes ignited with lust.
"I was hoping that you would share my fantasy with me," I said. Her reply told me that she would.
Without saying a word, Amy threw her arms around my neck and jammed her tongue into my mouth. We both kicked off our shoes and laid back on the sofa, our tongues darting around exploring each others mouths. Somehow we managed to make it to my bedroom.
We fell onto my bed groping at each others breasts. I pulled off her top exposing her breasts which were encased in a lavender colored, satin demi bra. Running my along her spine to her waist, I began to slowly undid the small zipper on the back of her pants. She laid back so that I could pull off her tight satin pants. Underneath she was wearing only a tight, skimpy pair of lavender satin bikini panties. Her legs were absolutely gorgeous. She leaned back on her elbows and, with her legs bent at the knee, spread her legs open. I ran my hands up her calves to her inner thighs. She cooed softly as I kissed her belly. I began licking the breast exposed by her revealing bra. Amy wrapped her legs around my waist and threw her hands around my neck. She kissed me deeply while running one hand down to rub my ass through my skirt.
I rolled off of her and pulled her on top of me. Amy ran one hand up underneath my top and started to fondle my tits, while her other hand ran up and down my stocking covered thigh. I took off my top and skirt. Amy immediately dove on me and started sucking and licking my tits through the lace cups of my bustier. Without looking up, she hooked her thumbs in the waistband of my panties and very slowly pulled them down my legs.
Amy moved her head towards my crotch and stuck out her tongue. She removed the drop of pre-cum that was perched at the tip of my dick. Without retracting her tongue, she moved back up my body and offered my pre-cum to me. I engulfed her tongue with my mouth as if I was giving head to it. I pulled her on top of me, stroking her breasts with one hand and tickling her satin clad ass with the other. I slowly and ever so lightly brushed my fingertips along her cheeks, almost bringing her to a long overdue orgasm in the process.
We broke our kiss and I moved my mouth down to her tits. I began suckling her nipples through her bra, and could feel how stiff and excited they were through the thin material. I reached back and undid Amy's bra, releasing her boobs from the confines of their satin prison. They were beautiful; a wonderful coffee color with hard brown nipples, and sooo soft and warm. She knelt on the bed as I sucked her tits with the urgency of a hungry infant.
Soon she pushed me down towards her crotch. I paused on the way to lick her soft, smooth belly. She arched her back as I did this, playing with her breasts, pulling and squeezing at the nipples. I placed both of my hands inside of her panties on her ass cheeks and started kneading her globes between my fingers. Amy laid back on the bed and spread her legs wide. Her crotch was soaked through and her thighs were starting to get wet with her juice. I licked the tangy wetness from her thighs, gradually moving closer to the source of that sweet taste.
When I at last reached her panty covered crotch, I licked up the length of her mound, and then took the crotch of her panties in my mouth, eagerly slurping and sucking her love juice from the fabric. When I had drained all the remnants of her passion from her panties, I pulled them down her legs and tossed them aside. Her cunt was magnificent, her vulva closely shaven and the patch above her slit carefully trimmed. The inner lips protruded past the outer ones, her clit was fully engorged and stuck out mercilessly begging to receive attention. I placed my tongue on her pert little asshole and licked up the length of her snatch, stopping just before I reached her clit. The heat coming off of her cunt was unreal. I spread her lips apart and worked my tongue around her pussy canal, being careful not to touch her clit. Amy was going nuts as I fucked her love canal with my tongue and then sucked her inner lips into my mouth, lightly nibbling on them. I put a little bit of her fuck juice on my finger and began massaging her asshole. When her anus was relaxed and enjoying being rubbed, I dove on Amy's love button. As soon as my tongue touched her clit, she shot off like a bottle rocket. Her legs wrapped tightly around my head as she cried out in orgasmic ecstasy.
"Oh, Melissa!!! Keep sucking meee, keep sucking..."
Her clenching muscles sucked my finger into her ass, heightening her intense pleasure. My mouth was soon flooded with Amy's sweet nectar. I licked every up bit that I could. When her orgasm had subsided and her legs released me from their grip, I licked my way up her torso. When our lips met, we fell into a deeply passionate kiss.
"Melissa, that was fantastic. Now it's your turn," said Amy with the wickedest look in her eye.
Amy pushed me back on the bed and spread my legs wide open. My cock was covered with pre-cum and Amy licked up every drop. With the pre-cum still on her tongue, she lowered her mouth to my ass and began licking around my brown ring. Her tongue maneuvered around my ring as mine had gone around her cunt tunnel. I relaxed my ass as best I could. Amy spread my cheeks as far as she could giving her the greatest access to my rectum. As I loosened up, she shoved her tongue farther and farther into my fudge tunnel.
Our eyes met and she stopped what she was doing and said, "See? I can eat 'pussy' too. And I know how to handle a 'clit'." And with that, she engulfed my penis, sucking it like a vacuum cleaner. She proceeded to milk all the pre-cum out of my dick. When she was finished, she got off the bed and grabbed the strap-on harness I had given her. She went into the bathroom. When she came back, Amy had a seven-inch cock. I moved to the edge of the bed and when she approached, I reached out and grabbed her cock. I stroked it up and down, loving the feel of it. Amy reached down and pushed my head towards her dick. I opened my mouth and took in the head. She placed her left hand on her butt cheek and her other behind my head and began bobbing my head up and down on her shaft. I opened up my throat to take as much of it in as I could. After a while, she pushed me off of her cock. I looked in her eyes and knew without asking that she wanted to fuck me.
I pulled a tube of KY from the night stand and poured a line of it down Amy's penis. I worked the dildo with my hand, spreading the lubricant all over. When her cock was good and slick, I leaned back on the bed and handed her the tube. Amy quickly placed some of the jelly on her finger and and lubed up my asshole, until my butt was literally dripping all over the sheets. She told me to get on my knees doggie style and moved around behind me. Both her hands were covered in KY and she started to massage my ass cheeks as I reached back to guide her dick to my heavily lubed cunt. I was so horny and slick that Amy's schlong slid easily up my back door. She paused for a moment to allow my tunnel to adjust to the invading phallus. She slowly began pulling out and driving back into my little brown cunt. As my hole loosened up, I began pressing back against her, meeting her thrusts. We built up a quick rhythm, and her dick entered deeper and deeper inside of me. Suddenly, the tip of her prick came into contact with my prostate, sending tingles all over my body.
The base of the dildo was rubbing against Amy's clit and it was not long before she came in a screaming orgasm. I looked back between my legs and could see her cum running down her thighs. As she was reaching the peak of her orgasm, I increased my pace, helping to drive her over the edge. When her climax had finished, I pulled her schlong out of my "pussy" and told her to lie down on her back. When she was comfortably laid out on the bed, I straddled her body and lowered myself down on her cock. Her penis once again brushed past my prostate. I moaned in delight, "Oooohhh yeahh."
Amy said, "Are you starting to cum?"
"Not yet, but you just hit my 'g-spot', sweetie."
I began riding up and down on Amy's sweet cock, taking it deep into my "pussy", forcing up past my swollen prostate. I placed my hands behind me and leaned back still riding that fabulous dick. I could feel an orgasm building and started crying out softly "Ummm." Amy was banging her pelvis against my ass as she thrust into me, eager to get me off. Suddenly I exploded into the best orgasm of my life.
My "cunt" muscles began clenching around Amy's cock as I pushed down hard to feel it deep within me. My "clit" started spasming, very slowly, and thick gobs shot up into the air falling back to land on Amy's tits and face. A gallon of semen poured out of my dick. It seemed as though my orgasm would never end, my muscles kept contracting so hard. I felt like I would pass out.
Finally, my body ceased to feel the intense pleasure that had just coursed through me. I eased myself off of Amy's dick, loving the slurping noise that accompanied her exit from my "snatch".
I collapsed on my back and Amy took my "clit" in her mouth, milking the last of my fuck paste from my softening tool. That done, she leaned over me and put her sperm coated tits in my face. I leaned forward and began to lick the cum from her breasts. When it was gone, I pulled her face towards me and began to eagerly lick the cum from her cheeks and lips. I took a huge glob on my tongue and fed to her. Amy took my tongue in her mouth and sucked the juice from it.
When I had cleaned the cum from her body, we stopped and surveyed the mess we had made. My "pussy" was dripping lubricant down my thighs and all over the sheets. I suggested that we should clean up a bit before continuing. We got off the bed and I took off my bustier.
As I bent over to take off my stockings, Amy noticed the lube coming from my hole. "Looks like you have a little leak there. Don't worry, I know how to fix that." She went into the other room and returned digging through her purse.
"Bend over the bed for a sec, Melissa." I did as instructed. Amy pulled a tampon from her purse and inserted it into my sopping "pussy". "There, that should take care of it."
We quickly cleaned up the mess from the lubricant and straightened up the bed as best we could. Amy brought out a pink satin chemise from her bag of clothes she had brought and handed it to me. I slipped into it, loving the soft feel of it against my skin. Amy changed into a red satin teddy with a thong back. The two of us slipped between the sheets and snuggled up for a nap.
I awoke a few hours later to find Amy stroking my "clit" through the satiny gown. I moaned softly to let her know I was awake. I turned to face her and threw an arm around her, stroking her ass hole through the thong back of her teddy. Amy rolled me onto my back and straddled me. I could see that kinky look in her eye again. She leaned down and whispered into my ear.
"Melissa, I want you to fuck me with that 'strap-on' you're packing," she whispered into my ear as she gently squeezed my balls.
I pulled aside the crotch of her teddy, wedging it in the space between her mound and her leg, exposing her glistening slit. Amy pulled up my chemise revealing my rock hard "dildo" and stroked it a few times before lowering herself down on it. My tool sank easily into her velvety love tunnel. God it was magnificent. Her silky walls grasped my rod like a vise as her juices coated my extension.
I grabbed the bottle of KY and coated my finger as Amy began to rock back and forth on my "strap-on" tool. I began luring her asshole, playing with the rim and sliding my finger a small way into her butt. With two fingers, I began stretching her rectum, and inserting my digits as far into her ass as I could. Amy was really getting off on the attention I was giving her ass. As I inserted a third finger, she came, her rectum contracting against my probing digits as her cunt spasmed around my fuck tool. I could feel her pussy juice dripping down into my crotch towards my tampon plugged asshole.
I was so turned on from watching her orgasm that I was nearly ready for my own. Without missing a stroke, we rolled over so that I was on top of Amy. I pushed her legs back toward her head and she locked her ankles behind my neck. I began banging into her hot, dripping, box as hard as I could, going all the way to the hilt and pulling out so that only my head was still inside her. Amy reached back and took one of my butt cheeks in each hand, squeezing them. I was nearing the precipice when Amy gave my dick a squeeze with her cunt muscles; I went head first over the edge, spewing my seed into her wet vagina. She milked my tool with her cunt as I finished emptying into her.
Amy lowered her legs as I softened inside of her. She pushed my head towards her crotch. I started licking our combined love offerings from her pussy, offering them to her on my tongue. After I had cleaned her up, she laid back and fell asleep.
And that's where she is now, lying in my bed on a visit to dreamland. And I'm sitting here in front of my computer recording the events. I got so horny writing this that I had to put a maxi pad in my panties to soak up all the pre-cum. Now if you'll excuse me, I have to replace my tampon with my lover's "penis"...
