I met Robyn in one of the chat rooms on Lush Stories. She too was a cross-dresser, but far more committed to it than myself. She was a full-time dresser on hormones and is probably considered a T-girl. It was a strange relationship. We were both gurls constantly looking for cock, yet, at the same time, teasing each other like two lesbians. With so much role-playing and cybersex amongst the multitude of participants in the chat rooms, it is difficult to separate reality and fantasy. I wasn’t sure if her invitations to fuck her were part of a game or a bonafide offer. Given our conversations to this point, neither of us were well endowed. Although, in my case, I could occasionally get a five-inch rock hard erection. However, with little need for it, the occasions were few and far between.
Our teasing continued for several months developing into an almost daily routine. While I so much enjoyed our relationship, I sensed an emptiness in Robyn. Whenever I described one of my recent experiences at one of the bookstores, she would reply with, “That sounds so hot, invite me next time.”
I always responded, “Sure, when would you like to go?” She would immediately move on to something else or just disappear from the chat room. I just assumed it wasn’t practical anyway.
One day during a group chat she revealed she lived in an adjacent county across the state line. I couldn’t believe she was so close. All this time I thought she was a thousand miles away. Then I thought to myself, maybe this is why she’s been so elusive. She wants to keep her distance. But, why would she give away her location? This just confused and frustrated me more. I didn’t want to lose her valued friendship, so I didn’t do anything that would put it at risk.
A few weeks later, in the chat room, I described an experience over the previous weekend when I was fucked in the ass twice in the same night. After several congratulations by some of the gurls, Robyn whispered privately, “When are we going to the bookstore together?”
I gave her my standard answer, “When would you like to go?”
To my surprise, she replied, “How about this weekend?”
Was this for real? Did she really want to go with me? Would I finally meet my idol? I couldn’t believe how nervous I suddenly became. I use an avatar on my profile. It is an image of what I wish I looked like. I’m nowhere close to looking like it. In fact, I don’t think I’m even passable. This is why I go to the bookstores in the first place. The men there are more interested in my anal and oral skills than my facial features. As long as I dress sexy, they treat me like a woman. This probably works in my favor since there are no surprises. They know what I am from the start and they’re going into a sexual situation with their eyes wide open. I don’t think I’ve ever disappointed any of them.
While still reeling from Robyn’s unexpected reply, I somehow responded with, “Okay. You name the time and day.”
“Is Saturday evening around seven good for you?”
I answered, “Yes. Where do you want to meet?”
“Let’s meet in the bookstore parking lot. Give me the address for my GPS.”
I frequent two bookstores. One has extensive accommodations: multiple theatres, rooms, and booths, along with the traditional store area. The other is much smaller with a store area, a few booths and three viewing rooms with a leather sofa and two chairs that seat, at best, five people. This was a better choice since there would be far less activity and people. It was also much closer to the state line and the area she said she lived. I typed in the address in the private mode and a description of my car. She responded, “It’s a date.”
I spent the following days going over how I would dress, what I would say, what we would do, and a million scenarios, including her not showing up. I have had a few rendezvous planned in the past and they all ended up as no-shows leaving me crushed. This would be a disappointment that I don’t think I would get over. I was a wreck all week.
Circumstances were in my favor on Saturday. I was alone for the weekend. I spent the entire afternoon getting ready. First, I douched my ass with a high-volume enema. Next, I used Nair on my legs, shaved everywhere else, showered, and soaked in the bathtub for over an hour in scented bath beads. Then, I painted my toenails and fingernails with a hot pink nail polish. Nothing says “fuck me” like hot pink.
After a week of deliberation in my mind, I decided I would wear a skirt and blouse, bare-legged, with open-toed shoes. My legs are one of my best assets and I wanted to show them off. Also, I love the thrill of the cold air blowing up my skirt. The shoes would expose my painted toenails, but were easy to walk in. Poor walking form is a dead giveaway for cross-dressers.
I started off with a red lace thong with a full front to keep things in place. Then, I put on a red full coverage “B” cup bra with medium size adhesive breast forms. While the full coverage bra is not as sexy as many of my skimpier bras, It keeps my breast forms in place, regardless of my activity. I didn’t want anything to be out of place tonight. I’d rather dress a little on the conservative side to be more convincing than to look like a pathetic old queer. Finally, I put on my maroon mid-thigh skirt and white blouse that left my bra quite visible through the material.
It was time for the hardest part: make-up. I began with a light shade followed by a darker shade in key areas to minimize my masculine features. Then I used mascara to darken my eyelashes. Since I keep my eyebrows short, I have a lot of choices with the eyebrow pencil. I made a long delicate curve with a sharp tail over both eyes. My choice of eye shadow has been poor in the past, so I used a light brown sparingly. I finished with a liquid lip gloss that stays on better than normal lipstick.
I decided to put my wig on before leaving and take my chances of being seen by my neighbors. I wanted it to look perfect and this was not possible using the car mirror in low light. The wig was dark with straight shoulder-length hair. Again, conservative, but fewer issues to stick out. Although I have never felt passable, it didn’t bother me much before. However, tonight was different. I combed the wig before and after putting it on.
It was almost time to go. I put on my shoes, bracelet, ankle bracelet, and necklace. Then, I dabbed on a little perfume. I put a pair of light bikini panties, a dozen condoms, two tubes of lube, paper towels, money, and breath mints in my carry bag. It was dark outside now. This would make my exit easier. I keep my car in my garage so the risk of being seen is minimized. I got in the car, opened the garage door with my remote, backed out, no one around, closed the door, and drove off.
Although Robyn said we’d meet at seven, I wanted to be there early. We didn’t exchange telephone numbers and her only way to identify me was the information I gave her on my car. I was already convinced that she was going to back out. If there was one chance in a million she was going to be there, I didn’t want to miss it. I arrived at the bookstore twenty minutes early. I must have looked at the car clock a hundred times while I waited.
A car pulled into the parking lot. My heart started to race. It passed by me and parked toward the entrance. It had in-state tags. It was a few minutes after seven. I started to prepare for the worst, she wasn’t going to show up. Suddenly, someone tapped on my window. I lowered the window. The woman asked, “Joannie, is that you?”
I couldn’t believe my eyes. She was beautiful. I nervously answered, “Robyn?”
“Yes, I am. I’m glad to meet you. Are you going to get out and give your girlfriend a hug?” I opened the door and got out. She gave me a big hug as she said, “I hope I didn’t scare you.”
I said, “A little I guess, I didn’t see you pull in.”
“I parked on the street around the corner. I’m always nervous around these places. I’m afraid someone will follow me when I leave.” Then she backed up two steps and asked, “Well, are you disappointed?”
What a package. She was tall and slim with a cute face and shoulder-length hair. She was wearing a tight one-piece black dress with black stockings and high heels. She was perfectly proportioned. Her skin was milky white. I thought to myself, if that’s what hormones do, I’m going to have to try them myself. However, I’m sure it was much more than that.
“Are you kidding me? You’re stunning. You’re everything I imagined, but even better. I should be asking you if you’re disappointed. I know I’m not all that and could never be as beautiful as you.”
“Don’t sell yourself short. Well, let’s go in, then,” she urged.
I reached into my car and grabbed my bag before locking it up. We walked around the building to the entrance and went in. I quietly said to the attendant, “Two for the theaters, please.”
He responded, “It's half price for women, that will be fifteen dollars.” I gave him a twenty-dollar bill and waited for the change.
Robyn said, “Let me give you half.”
I responded, “That’s okay. You can pay next time girlfriend.” Then, I took her hand and we walked to the door with a “three” on it. “Let’s see what’s behind door number three.”
I already knew what was behind the door. There are three of these small rooms in this bookstore. One price gets admission to all three. One of them has videos featuring gay men only, one has T-gurls, and, number three, has men and women performing traditional anal, oral, and vaginal sex. The men in the bookstore constantly move back and forth between the three rooms trolling for their prey. It was only a matter of time before they found us.
I guess it was still early. We sat on the couch by ourselves for ten or fifteen minutes watching the video. There was a well-hung guy getting a deep throat blow job from a naked woman. Robyn commented, “Wow, that’s a nice cock!” She rubbed my thigh a little. “Joannie, you have the smoothest legs I’ve ever felt. What’s your secret?”
I told her, “Nair. Unfortunately, they will only feel like this for a day or so.”
Just then, a man walked into the room. He stopped and did a double-take. After standing there for a few minutes he began rubbing his crotch. Robyn said, “Well, is Dick coming out to play?”
He didn’t need any more coaxing than that. He unbuckled his belt, lowered his pants, and began stroking his cock. It was average-sized, about six inches. Robyn giggled, “Dick looks lonely, why don’t you bring him a little closer.”
He took a few steps towards us. Robyn stood up, leaned over, reached out, and jerked him off a little before putting his cock in her mouth. After a few minutes, she stopped and looked at me, “Could you be a dear and take care of my back end, please.”
My goal is always to get myself fucked in the ass. But, how could I say no to her? I began to rub her ass. She had such a beautiful and sexy body. It was making me hard. I pulled up her dress and pulled down her panties under her garter belt. I leaned over and kissed up and down her soft and smooth cheeks. She was all woman and she was bringing out the little man I thought was long gone.
I reached over to my purse, took out a condom, removed the wrapper, and rolled it onto my hardened cock. I squeezed a small dab of warming lotion over the condom. I rubbed the tip of my cock between her firm and separated cheeks to locate her rear door. Then, I gently pushed forward slowly penetrating her. She was so warm inside as I passed through her sphincter into her colon. She gave off a soft moan of approval. I knew from chat room talks that she loved to be “spit-roasted”.
Suddenly, the door opened and another man entered the room. He stood there, like the first, doing a double-take on the situation. I invited him over, “There’s room for another behind me.” He didn’t waste any time. He came over, pulled up my skirt, and pulled down my thong. I could hear him unwrapping a condom, probably the one I left on the couch next to the warming lotion. He began probing between my cheeks with his cock that I had yet to see. While I couldn’t tell how long it was, I could certainly feel its girth.
He started to penetrate my ass with the large round tip of his cock. My anal ring was stretched like a balloon as it forced its way inside me. I could feel the raised nubs of the condom sliding through my sphincter. I love that feeling. He must have been at least seven or eight inches long as it felt like his entry took forever. I had never been in a daisy chain before this. It was phenomenal.
My hands were on Robyn’s hips. Her hands were on the first man’s waist. His hands were on her shoulders and my man had his arms wrapped around the front of me with his hands on my tits. The man behind me was setting the pace. Every time he thrust forward into my ass, he pushed me forward into Robyn’s ass, in turn pushing her mouth over the first man’s cock. We were all grunting in unison. We went on like that for at least twenty minutes.
