Company’s Coming

I have been crossdressing for several years. I am married to a supportive wife who shops for me and helps with my makeup. She also color coordinates my lingerie and outfits.

This Thanksgiving Day was special. After my morning shower, Daisy suggested I put on my makeup and an outfit she had laid out. There on the bed was my red lingerie and a new red dress. The dress was trimmed with lace at the neckline and hem, and it was so short that it just barely covered the hooks on my garter belt when I sat down. Daisy said the new dress was my first surprise. She had another surprise in store.

I lounged around that way till about four in the afternoon, when my wife said, “Touch up your makeup. Company will be here for dinner soon.”

I knew of only two people she could possibly have invited. One was a transvestite friend of mine, the other a girlfriend of hers who lived several miles away. Her friend knew about me, though she’d never seen me “dressed.” When the doorbell rang, sure enough, it was Daisy’s girlfriend Barbara. Compliments abounded as to how nice I looked.

We had dinner, cleared the table and sat down to relax and talk. Barbara had brought me a video. Some time earlier she had given me several videos that her ex husband had left behind when they divorced. My wife suggested I put the tape in the VCR.

The video was very steamy, and about five minutes into it I was hard as a rock. My erection formed a tent in the front of my dress. I was sitting on the couch between my wife and Barbara, and I didn’t see how they could help but notice my hard on.

As I was wondering, Daisy said, “Take that dress off.” I was about to leave the room when she said, “Take it off here.”

I returned to the couch, and she unzipped my dress. It fell to the floor. Then she said I should sit back down, and there I was in my lingerie and heels, sitting between these two women, with a huge hard on pushing against my panties.

With the video still playing, my wife said, “Rub it through your panties.”

Feeling a little foolish but also excited, I did just that. After about five strokes, come oozed through my panties.

Daisy then said, “Why don’t you go clean up and then put on that baby doll outfit, the one I got you last week?”

After I returned, changed, the three of us put up the Christmas tree. Barbara finally left around eleven. After she left, I asked my wife why she had put me on display in front of her friend.

She said, “I had to prove a point to Barbara.”

It turns out that before Daisy met me, she used to do threesomes with Barbara and her then husband. She explained that she had found a pair of come filled panties in the laundry and mentioned this to her friend. Barbara, however, did not believe that married men jack off. Daisy had devised this way of showing her that at least this one does.

It was a Thanksgiving to give thanks for, and to remember!

N.G., Olympia, Washington

REST STOP PASSION

I am a forty one year old crossdresser. I have dressed up in private since I was in my early teens, and I can get to looking pretty good, given enough time to prepare. But until recently, I never tried to venture outside. Last week one of my fantasies came true.

I was driving down the interstate late in the afternoon, and I decided that I could dress in women’s clothes after it got dark and not worry about being recognized as a man. So I stopped at a gas station and put on some panties, pantyhose, a bra and a short spandex dress that I had with me in the car. Then I put my regular clothes on over them.

I got back in the car and continued down the interstate, and as it got darker I began getting more anxious. When I decided it was dark enough, I pulled onto an exit and drove down a back road a ways. I stopped the car and took off my pants and shirt, and then put on high heels, a wig and makeup. I had to use the rearview mirror for this, so I couldn’t really see how good or bad I looked.

As I drove back down the interstate I got more and more aroused. When I saw a rest stop ahead, I decided it was time to be brave and stop in. I parked away from the other cars, and after a few minutes of building up my nerve, I got out. I pretended to look for something on the backseat. With my short dress, I gave everyone quite a show when I bent over. There weren’t many people there, but I did get a few looks from the guys.

I stayed about ten minutes and then decided that I’d better get going. I got back on the interstate, and as I drove on, all I could think about was how great it felt to be in front of people like that. When I saw the next rest stop sign, on a sudden impulse, I decided to stop there and try it again.

When I pulled in, I once again parked away from the other cars, and I got out just like last time. But this time I walked around like I was waiting for someone. There were more people at this stop, and the guys kept looking at me as they walked from their cars to the building. There were also some guys who just sat in their cars and stared.

Each time I thought someone was coming toward me, I walked back to the car. As I got braver, I went to a lighted phone booth and pretended to make a phone call. Suddenly a truck with two men in it pulled in next to my car. A young man got out of the truck and made a beeline for the building, obviously needing some immediate relief.

I stood frozen, knowing there was no way I could get back to my car without the other guy seeing me and perhaps realizing that I was not a woman. So I stood there, trying to look as if I was waiting for someone. Suddenly the second man stepped out of the truck and stood leaning against the front of it. He kept glancing at me, until finally he started walking toward me.

I turned away and tried to ignore him, but he walked right up to me and asked if everything was okay. So here I was with my low voice, hairy arms and muscular body. How could I ever expect to fool anyone? I had no choice but to attempt to be as feminine as possible.

I spoke with as high a voice as l could and told the trucker l was fine and I was waiting for someone. He said it was kind of cold out to be dressed the way I was. I was shaking from excitement, and I was actually very hot by then. I don’t know if he saw me shaking and thought I was cold, but he offered me his jacket. I told him I was fine just like I was and didn’t need it.

Then he asked if I would like to sit in their truck and wait. I just looked at him and said he must be kidding. Then he said if I preferred, we could sit in my car. I said, how did I know that he didn’t have a weapon and want to kill me? He leaned up against a tree with his back to me and told me to frisk him.

I just stood there, but he kept telling me to. I finally walked over and patted his arms and down his back to his waist. I stopped and said okay, but he said I’d better check his legs. I felt his ankles and up his legs. As I moved up, I continued to get excited. Instead of patting, I slid my hand a little way up his thighs.

When I stopped, he turned his head and asked me, hadn’t I better check in front for that weapon? Now I was to the point where I wanted to continue, so I walked up to him he still had his back to me and put my arms around him. I felt his chest and slowly moved down to his waist. Then he took my hands and moved them to his crotch.

Sure enough, I found his weapon. I asked him what kind of gun that was, and he said if I would go to the car with him, he would be happy to show me. I just stood there, not knowing what to do. Suddenly he turned around and kissed me. I’d had men give me head before, but I had never kissed another man. I must admit it was unusually exciting.

Then he put his arm around me and we walked to my car. His friend had returned and was sitting in their truck watching the whole thing. We got in the car and he kissed me again, only this time he used his tongue. As we kissed, he ran his hand up my hose covered leg to my thigh. I reached down and pushed his hand back, but he took my hand and put it on his crotch.

I could tell his penis wasn’t real big, but it sure was hard. As I undid his pants and began to stroke him, he put his hand on the back of my head and gently pushed me down. I didn’t resist, though I did wonder if I was really ready for this to be my first time.

I guess I was.

I rubbed his dick across my lips and face, and then softly licked the pre come off the tip. Then I slid it between my lips. I found I could fit it all into my mouth without much trouble. He pulled his pants down, and I ran my hand up his thigh to his balls. I tried to do everything the way I had had it done to me so many times before by both women and men. I would pull it out of my mouth and lick the shaft and then run my tongue all around the head before putting it back in my mouth.

As I went up and down on him, he pushed his hips up to meet me. Soon I heard his moaning getting louder, and he told me he was about to come. I was so excited by then that there was no way I was going to stop. I pulled my mouth away a little and opened wide as I stroked him with my hand.

Suddenly the first shot of come hit the top of my mouth and dripped onto my tongue. He continued to fill my mouth as I slid my lips slowly back around his throbbing member. I had tasted my own come before, but eating your own come can’t compare with having someone else’s hot, salty, sticky juice in your mouth. I continued licking and sucking until he was finished and got soft. I sat there on the seat next to him and we kissed again.

Then he told me it was his friend’s turn. I was still very excited, and I was more than happy, maybe even eager, to help his friend. The guy I had already done signaled to the other one back in the truck. When the other guy got in the car, he just pulled his pants right down, exposing a penis that was slightly larger than the first guy’s.

I began working on him, and the first guy began feeling up my thighs. I pushed him away once or twice, but he was persistent. I finally had to stop and tell him to give it up or they could both get out and leave. I will always wonder how it would have felt to have him plug me from behind and come inside me while I took care of his friend, but I couldn’t let him know that l was really a man.

He finally stopped, and I continued working on his friend’s dick. It wasn’t long before he was ready to pop. I continued to lick and suck him until he shot a huge load in my mouth. I swallowed it all and licked him clean. Then I sat there between the two guys.

They kept trying to feel me up, but I kept stopping them. If they hadn’t figured it out already, I didn’t want them to find out now that a man had just given both of them head. We sat there for a few minutes, and then I kissed each of them good bye and drove away. I will never know if they actually knew that I was a man. But I will always remember my first night out of the closet.

R.T., Gainesville, Florida

YOU’RE MY BOY, GIRL

I’m a 25 year old male. I’ve often been told that I have feminine features particularly my face, legs and butt. This has never bothered me much, and I never thought too much about it. The girls always seemed to really dig my androgynous looks, so I didn’t particularly care.

Six months ago I had an interview for a job as an assistant to an ad executive. At the interview the executive, whose name was Dan, said he liked my appearance and wanted to hire me. I was ecstatic because the position was just what I wanted.

Although Dan had told me he was married, after my first week there I began to suspect that he was also attracted to men and to me in particular but I brushed it off. Live and let live is my motto, and as long as his attentions didn’t get too obnoxious I wasn’t about to let them bother me.

About a month after I was hired Dan and I went on an out of town trip for a business conference. Over dinner one night he told me that he liked my work so far and was considering giving me a healthy raise. I liked the sound of that and told him I would do my best to deserve it.

That night I was in my room relaxing, when a knock came at my door. It was a bellhop with a large package that turned out to be from my boss. Inside was a black minidress, black stockings, a garter belt, a fully padded bra and matching panties, high heeled shoes, a large blonde wig and a complete makeup kit including several different shades of lipstick, perfume, a razor and shaving cream. On top if it all was a note from Dan, suggesting that I shave completely, put on the clothes and wig, get totally made up and then come to his room and knock three times.

I was stunned. I sat on the bed for about 15 minutes before I made up my mind. I couldn’t believe how I was feeling. I had never been with a guy before, and I would never have thought of doing this by myself, but now that I was presented with the idea it made me kind of curious. Well, more than curious…. It actually made me excited.

It took me a while to get ready, but by 11 o’clock I was set. I looked in the mirror at my totally shaved body, complete with boobs, makeup and wig. I looked exactly like a girl I looked like my own sister, in fact. It was weird. I did think I looked very sexy, though, as I turned around and checked myself out.

With every ounce of nerve I could muster, I made my way to Dan’s room. I knocked three times as instructed, and he opened the door. “Wow! You look awesome,” he said as he let me in. Nervously I thanked him, and he gave me a stiff drink, which I downed quickly. He gave me another and told me to relax. We talked about the situation for a while, and he explained how he needed to trust me, and that no one at work could ever find out. I agreed.

After two more drinks I was feeling no pain. I was sitting on the edge of the bed with my legs crossed, and Dan sat next to me. As we talked he nonchalantly put his hand on my thigh and caressed me. I didn’t know what to do, so I did nothing. He asked if I was nervous, and I said yes, that I’d never done anything like this before. He understood, he said.

His hand was now at my stocking tops under my dress. He asked if it felt good, and I said yes. He continued upward until he reached my cock, which was hard under the thin black panties. He felt me up and then pushed my skirt up a little and took my cock out, stroking it gently. Then he got down on his knees between my legs. He lowered his head, took me in his mouth and then began licking and sucking my dick.

It felt great! He massaged my balls as he sucked me, and soon I felt myself getting close to coming. Then I felt his finger at my ass, slowly entering my back passage. It was awesome! I began bucking uncontrollably, and I shot my come into his mouth as he swallowed it all.

When I finished he stood up, wiped his mouth and sat next to me again. Then he took out his cock, which was quite big, and simply said, “Suck it.”

I got on my knees as he had done, slowly lowered my mouth and licked the head of his dick. It was salty. Next I opened my mouth and took the head into it. Dan put his hand on my head, as if to encourage me, and I tried taking more, but I couldn’t. I tried again, and as I gradually got over my nervousness I found that I could relax my throat muscles to take in more of him. From then on I tried to copy what Dan had done to me. Soon my head was bobbing up and down, my hands rubbing his balls. When I fingered his ass he went over the edge. “Here it comes!” he moaned. I tried to pull back, but it was too late, as he was already shooting in my mouth. I found I liked the sensation, and as he shot his jism into my throat I swallowed as much as I could.

Dan told me to keep sucking, so I did, and soon he got hard again. Then he told me to get on the bed on my hands and knees, with my ass in the air. I knew what was coming now, and I was nervous and excited all at once. He got behind me and pushed up my skirt, and I felt something warm being applied to my ass. Then I felt his finger sliding into me, loosening me up a little.

Next I felt his cock at my ass, and he told me to relax as he started to push. My eyes flew open and I gasped as he penetrated me, and then I began to moan with pleasure. He kept pushing until he was in me almost completely. Then he gave a final push and rammed the last inch in. I couldn’t believe how good it felt as he began fucking me. My own dick was hard again, and he reached around to stroke it for me. I soon came, shooting my load onto the sheets as he picked up the pace.

After a few more minutes or so he stiffened and began to gasp, and I felt him shoot his come into my no longer virginal ass. It was very warm, and my ass tingled as he pulled out and we both collapsed.

After that I came to his room every night for the rest of the week we were there. I didn’t always wear the clothes and wig, but we sucked each other’s cock, and soon I was fucking his ass the way he had fucked mine. I found myself looking forward to those nights more and more.

On the next to last day of the conference, Dan asked me to be sure to wear the full costume that night. When he opened his door for me I was shocked to see two of our clients present. Nervously I went in, and after a few drinks I wound up being sucked and fucked by all three of them. Most of the time I had a cock in my mouth and one in my ass at the same time.

I was in heaven.

Ever since that trip my feminine wardrobe has expanded, and Dan and I have used my looks and my talents to seal a lot of deals. At one seminar recently, I was on my knees for about three hours while four men formed two lines, one behind me and one in front of me. I just love being what Dan calls a come slut now, and have become an expert at fellatio. This is without a doubt the most fulfilling job I have ever had.

Name and address withheld

Not That He’s Gay, But—

My favorite letters have always concerned crossdressers and lovers of feminine clothing. Since I was a boy sneaking into my mother’s underwear drawer, I have been wearing feminine things at every opportunity.

Recently a golden opportunity arose. While house sitting for some friends, I quickly discovered that all the woman’s clothing fit me perfectly. She’s a glorious size eight and so am I.

On my first night, I spent the entire evening trying on all manner of dresses, skirts, suits, lingerie and evening gowns. I began by choosing my lingerie very carefully. I settled on a lovely white underwire brassiere and matching panties. She also had several camisoles and half slips. The light blue looked most stunning. Various colored stockings depended upon which outfit I was wearing.

Since I owned my own dark, long haired wig and makeup, I was able to complete my transformation. I get such an erotic sensation while applying my makeup. After looking at several women’s magazines, I try to model myself after a particular advertisement. Since I am nearly hairless with soft skin, I am able to create an alluring female face. I just love applying eyeliner, eye shadow and then mascara to create sexy eyes. Finally, I apply a sensuous lip gloss and smack my lips together. When I view my complete self in the mirror I nearly faint from seeing the attractive and erotic fox that I’ve become.

The next night of my house sitting, I made myself up again, this time using a black full slip. Against my brighter lip gloss and red stockings, the contrast was very sexy. I wore a lovely black dinner dress with a sash around the waist. I looked so pretty I came close to climax. After measuring my figure, I stood at a presentable and very becoming 36 28 35, and one hundred twenty five pounds.

I was feeling very comfortable now in a complete outfit. Convinced that I looked every inch a lady, I donned my house owner’s faux fur coat and went for a drive.

I drove to the bank machine and went window shopping at a couple of malls after closing. When I looked in women’s store windows, I became hard and excited by my erotic reflection.

Several cars drove by during this time. Two honked their horns and the drivers whistled at me. I felt really good and truly feminine.

I secretly wished someone would try to pick me up. Although I’m not gay, erotic, feminine desires arise in me when I’m dressed as a woman. At such moments, I long to feel a hard, hot cock inside my mouth. I want to rub my glossy, red lips over its length, engulfing its head and sucking its hardness. I would slide it in and out, eagerly and lustfully, until its owner came. Swallowing as much as possible, I would save some and kiss my lover hard and warm on his mouth, filling his oral cavity with our shared lust juice. Then I would leave.

This is my erotic dream and I thank you for letting me share it with you. I hope you will continue to print as many letters from crossdressers as you receive.

B.C., Portland, Oregon

He’s in Her Pants

I guess I should start from the beginning to try and explain this. I’m six feet two, have a pretty lean build and have always loved women. Everything about them: their bodies, their smell, the way they move— their panties.

I love women’s panties. Often, before sex with my wife, I’ve insisted that she wear a pair of lacy panties. But it gets deeper. I’ve also enjoyed wearing them.

I began by sneaking into my wife’s panty drawer to steal a pair and head to the bathroom to put them on and jack off. I’ve always been careful never to splash semen on them. Also, I’ve never told her, fearing she’d think I was crazy and leave me.

About a month ago, I finally got the nerve to confess to her my love for panties and the thrill of feeling my cock being pressed tight to my body under the silky lace trimmed panties I’d put on. She told me she didn’t mind and found it right damn sexy! What’s more, she knew I had been in her underwear drawer. So that broke the ice!

Now it was time to show her what I’d been looking at in the bathroom mirror. I decided to clean up a little and trimmed my pubic hair short, then shaved it into a nice V shape the way women do, only I included my balls. Then I took a long shower, dried my body and slid on a pair of white silk panties with tiny little bikini sides and a little pink bow in the center.

Once I was ready for bed, I dropped my pajama shorts to the floor and got into bed. Moments later, my wife came to bed and we lay talking as usual. I started rubbing her leg and continued talking. I could tell she was getting turned on. She reached over and started rubbing my belly, working her way to my hardening, panty bound prick. Her fingers hit the tiny silk strings and her eyes widened as they met mine.

She let out a little moan, then began caressing my cockhead and shaft through the silky material, dragging her fingernails lightly up and down my length.

I was going crazy! She finally pulled the elastic band from my waist to the underside of my balls, freeing my love muscle. Breathing heavily, I begged her to suck my dick. With no hesitation, she swallowed my shaft into her mouth and worked her tongue on my purple swollen head, while massaging my heavy sac of nuts with her hand. I began pumping my prick hard into her mouth.

I was getting the feeling I was about to come when she thrust her index finger into my untried asshole. Never had I felt such a sensation. I grunted loudly and ejaculated a hot load of spunk down her throat. She didn’t slacken or miss a drop until my dick was limp.

She slid up to me and we kissed deeply. I tasted my salty juice in her mouth. She was hot, grinding her cunt against my leg and tweaking her nipples between her fingers. Within seconds I was hard again. I rolled her onto her back and threw her thighs over my shoulders. I spread her moist pussy lips wide and drove my hard cock deep into her waiting hole. She moaned loud and bucked her hips to meet mine. I began ramming my pole into her as she moaned, “Yes, yes, fuck me hard!” She clenched her teeth tight and her body began shaking.

I couldn’t hold out any longer. I emptied myself into her hot hole. Then we lay together, sweaty and exhausted, and fell asleep.

Now she goes shopping for me, buying me panties of all kind: lace, silk, G string, bikinis. Nothing gay or bi about me, folks. it’s just that I love women and I love their panties, on them or on me!

G.W., Elkhart, Indiana