Confessions of a Sex Crazy Cross Dresser Part 4

By cassandrababy

Original link:

Tags: Crossdressing, Sex, Anal, Threesome, Drugs

Added: 28 May 2010 Views: 9852 Avg Score: 4.8

Chapters 7 and 8 of Book #1
Hi Everyone, I hope you like these chapters, please let me know if you want the next two.

Chapter 7: Triangle of Fun

I slept great that night with a full stomach of drink, food and Peter’s cum. I woke up on Friday and thought this is going to be a hell of a weekend. I played around with my cameras and had finally figured out how to use the self timer on the 35mm and how to use all the options on my movie camera. They were both relatively new as I bought them in Phoenix, just before moving back to California.

Although, I was not going to work on Friday, I had a couple of calls that changed my whole plan for next week. A couple of additional accounts wanted to see me and my meeting in Vegas got pushed back a couple of days. It turned out the only way I was going to be able to do this trip effectively was to make it a two week trip and to drive the entire trip.

I called my travel agent and arranged a rental car (I didn’t want to put all those miles on my own car) and hotels for the entire trip. It was going to be a lot of driving, but it should be a very productive trip. I called Buddy at “Da’ Place” and asked him if I could park my car at the bar for a couple of weeks. The rental car dealer was about a twenty minute walk from the bar. He said no problem, so I told him I would see him around 5 PM and give him the keys to my car.

I decided to run a few errands to pick up stuff for my trip, so that I would not have any interference in enjoying my weekend. I wrapped up all of my projects and was back in my apartment at 3:00. I decided to go check out Sheila’s apartment and see what I had to do in regards to watering tomorrow and to do some snooping.

I walked upstairs and let myself in her apartment. I counted five plants in the living room and a one each in the kitchen, bedroom and bathroom. Next I went into her closets and checked out her wardrobe. There was a nice assortment of dresses and suits. Her drawers were well organized and I found a nice assortment of lingerie, swim suits and sweat shirts.

Now that my little exploration was complete, I returned to my apartment and decided to drive down to drop of my car. I stopped first at the rental car office and signed all the paper work and got the keys. I had decided to get a van, as I had to carry my samples for work and suitcases and this would be the best for such a long road trip. I told them I would pick up the van after they were closed sometime tonight around 9 PM. Next stop was my bar and I found Buddy sitting at the bar stool on the end waiting for me. We talked for a while and I drank a couple of rum and cokes (I had to have Bacardi) and gave him my keys. He said he would take the car and leave it at his house and then bring it back here so it was waiting here when I returned.

Buddy left around 7:00 and I chatted up with Cathy the bartender. Cathy was about 40 years old and was a big girl. She was around 5’ 8” and probably weighed 180 pounds. She was a great bartender and could be very tough if anyone gave her “shit”. I thought she was one of the nicest people I ever met. She was always very nice to me and tonight was no exception.

She was telling me that Buddy was so happy I was dropping off my car, that I was his favorite customer, that I was such a great guy, on and on. I was laughing that Buddy thought so highly of me, after all I was just a regular customer, but I guess he felt I was one of the best dressed, smartest, kindest customers. Cathy was getting ready to leave her shift as Dave the other bartender had arrived and he was working from 8 until closing. Cathy asked me if I wanted a ride to pick up my rental car. I agreed and we left out the back door and got into her car. We drove down the street to the rental car dealer. We pulled into the parking lot next door that belonged to a bar I have never visited before.

“Have you ever been in Tango’s before?” Cathy asked while she pointed in the direction of the bar.

“No, I haven’t. Isn’t that a gay bar?” I asked.

“Sort of, mostly gays, but usually there are some straight people too.” Cathy said.

“So, let me buy you a drink then at Tango’s for driving me to my car.” I offered.

“I tell you what; I will meet you in 10 minutes. My apartment is a half a block down the street. I will park and change out of these clothes and meet you there, order me what you were drinking earlier a rum and coke.” Cathy said.

I agreed. I walked over to the Rental Car lot and found the van I had rented earlier. I drove it over to the adjacent parking lot of the bar and walked inside the bar. It was not too crowded as I thought (based on the cars in the parking lot). There were probably around fifteen to twenty people most sitting at the bar. It was a good sized bar with about twenty stools. It was one big room with six booth style tables against the wall and probably five small “pub style” tables with stools in the center of the room. There was a fancy jute box and a small stage at the far end of the room with a small dance floor. There was also a smaller room in the very rear that looked to have a pool table and maybe some other entertainment items.

I sat at a stool in the middle of the bar next to a man on my left side and empty seat on my right that I was going to keep for Cathy. The bartender approached and asked me what I would like and I ordered two Bacardi and Coke. I told him someone would be joining me in a minute. He returned with two drinks in a tall skinny glass that featured a lime wedge on the rim. I squeezed the lime and dropped it into the drink and sampled his drink. It was very good and very strong.

I looked up and said to him “Great drink! Not to be picky, but can I get a bucket, instead of a tall glass?” I asked.

“Sure” he replied. He brought a bucket glass and poured my drink neatly from the tall glass into the tumbler. “My name is Glenn” and stuck out his hand to shake.

I introduced myself and in no time I learned about Glenn and Tango’s. I was halfway through the drink and Cathy walked in. By this time, Glenn told me he was 55 years old and owned this bar for about five years. His lover John and he moved from Laguna Beach to Pasadena to buy this bar and be semi-retired. I am sure he thought I was gay, especially after Cathy walked in. Again, I think Cathy is great, but she does look like the prototypical “fag hag”. Cathy and Glenn introduced themselves to each other and we met the guy next to me and a few others in the bar and before I knew it I had finished six rum and cokes, two tequila shots and was pretty much hammered.

During the night Glenn told me more about Tango’s. He estimated about 75% of his men customers were gay and 25% straight. His busiest nights were Saturday and Wednesday. I asked him about cross dressers and he said occasionally some came in, usually on the busier nights. The time was flying by and before I knew it, I looked at my watch and it was 11:30. Cathy was drunk, too and she had worked her charm with Glenn to get us some cocaine. I gave her $60 to buy the stuff and we left shortly thereafter. We drove my rental van the ½ block to Cathy’s place, so that it would not sit in the bar parking lot. .

She had a small house she rented with her friend Lana. It was a two bedroom older home with one bathroom and a nice sized living room. I had been over on one other occasion to watch a football game with a group of people last year. Lana was a nice girl about my age, also kind of big. She and I had fucked each other a couple of times, without Cathy knowing, so this was going to be interesting.

We walked in and Lana was there on the couch. She was drinking a glass of wine watching television. She was wearing a pair of shorts and a tank top as the house was very warm.

“Tony, what are you doing here?” Lana asked with a big smile on her face. She jumped up and gave me a big hug and a nice kiss on the cheek.

Lana was the opposite of Cathy in many regards. Cathy was tall about 5’ 8”, Lana was short about 5’ 0”. Cathy was brunette, Lana blond. Cathy had long hair, Lana short. Cathy had big tits, so did Lana. Well not complete opposites, I guess.

“We bear presents, Lana.” Cathy said.

She went over to the coffee table and opened a drawer; she removed a mirror about the size of a letter sized piece of paper and a fresh razor blade. I rolled up a $20 bill and Cathy poured out a healthy amount of coke on the mirror. “I think he gave us an eight-ball for only $100. He must have really liked you, Tony”. Cathy said.

We filled in Lana the story about Tango’s and Glenn. Lana had poured us all drinks and in no time we were smoking cigarettes, drinking and snorting lines of cocaine. We were all drunk and high as a kite and feeling really good. I excused myself and went to the bathroom which was located at the end of the hall way off of the living room. I passed by both bedrooms and reached the bathroom. On my way back when I passed Cathy’s bedroom, she was standing in the door and grabbed my hand and pulled me in. She put her arms around me and said “Kiss me.”

I was kind of surprised, but I gave her a kiss and slowly it turned into a passionate wet stick your tongue into each others’ throat kiss. We broke off the kiss and she gave me a playful push into the hallway and strode past me into the bathroom. When I entered the living room, Lana called me from the kitchen to help her with the drinks.

When I arrived in the kitchen, I knew I was in trouble. Lana pulled me close and kissed me deeply. She is so short she wrapped her arms around my neck and wrapped her legs around my waist and pushed me towards the cabinets so I could stand up straight. She kissed me deeply and whispered in my ear “How are you going to fuck me tonight? I am so horny and I want you so bad.” She kissed me very passionately as we heard the toilet flush in the bathroom.

She jumped off me and handed me a new drink. I went back into the living room lined up six little lines and rolled up a new bill. Lana and Cathy arrived about the same time. Lana gave Cathy her new drink and they sat down on the couch next to me. Lana was on my left and I gave her the bill and she inhaled ½ of one line with her left nostril, and then finished the line with her right. I did a line in an identical manner then Cathy did her line. We all had a drink and lit up a cigarette. Lana was sitting cross legged on the couch with her tight shorts hiking all the way up her leg. She was leaning her head on my shoulder and was turning me on with her tight tank top showing off her big tits.

After a minute I handed her the bill and she started on her second line. As she bent over Cathy placed her hand on my thigh and leaned over and kissed my neck. She rubbed her hand up my leg and brushed against my crotch as she was kissing me. When Lana finished her line she looked up and started to hand me the bill, she saw Cathy’s hand and Cathy removing her lips from my neck. She looked at me with an inquisitive look that read “What is going on?” I shrugged my shoulders and handed the bill to Cathy who started on her second line.

Lana scooted right up next to me so that our legs were touching each other and she put her arm around my back and placed her hand on the back of my neck. Cathy finished her line and did not even seem to notice the new position of Lana. She handed me the rolled up bill and as I was snorting up the line she rubbed my leg with her left hand. I finished my line and leaned back on the couch. Cathy turned sideways and slid her hand up my thigh. Lana placed her hand on Cathy’s and slid it further up my leg so that it was right on top of my crotch and my growing erection. Lana slid up to me and kissed me on the mouth, a wet deep probing kiss while Cathy rubbed my erection. Lana turned to face me on the couch by straddling my left leg with both of hers. I saw Cathy move up and start kissing my neck and felt her stick her tongue inside my ear.

Well, I am not saying either of these girls were much to look at, but I had never been in a threesome before and I was getting pretty excited. Cathy stood up and moved the coffee table away from the couch and it cleared about a ten foot square area. She went into her bedroom and came back with a couple of comforters and spread them on the floor. Lana stood up and pulled me up from the couch and started to undress me. As she started to take off my clothes, Cathy was pulling off her top and pants. She was now in her bra and panties. It took Lana ten seconds to take off her tank top and shorts as I lay down on my back on the comforter on the floor. Cathy was now naked and she immediately started on my cock. She put her head down between my legs and started licking my balls and stroking my hard dick. Lana lay down beside me and kissed me on the lips then she sat up and placed her pussy right over my mouth.

I had eaten at this diner before and it was one of my favorite locations. She loved to have her pussy eaten and tonight was no exception. She was dripping wet and moaning in no time. I was as hard as a rock as Cathy continued to suck my cock. I felt Cathy get off me and she crawled up so that her face was next to mine. Lana scooted down and said “I am going to fuck that cock right now!”

She slipped her pussy on top of my dick and it felt sensational to have Lana’s tight pussy around my cock again. She sat up erect so that her tits were straight ahead and Cathy wasted no time. She sat on top of me with her pussy just above my mouth while she started licking and playing with Lana’s jugs. Lana reached out and started playing with Cathy’s tits as she rode my cock up and down. I started eating Cathy’s pussy and started slipping my tongue up her asshole. We were in this position about fifteen minutes and I heard a familiar moan from Lana that she did in anticipation of her orgasm. She did not disappoint me as she screamed out “I am cumming!”

She pulled her chest away from Cathy as Cathy dismounted my face. Lana started riding my cock like crazy! Up and down at a rate that was like a jack hammer. I met her as best I could by raising my ass off the ground trying to shove my cock deeper in her cunt. “Fuck me Tony, Fuck me like only you do!” She screamed.

Lana looked so hot! Her short little body flying up and down on my dick as her big tits flopped up and down. She was so fucking sexy acting like a sex craved nymphomaniac

fucking my cock. Her orgasm was so deep and strong she collapsed on my cock and her body fell down upon mine. “God, I love fucking you Tony! That was great!”

I kissed her passionately and then turned to my right and kissed Cathy deeply too. Cathy and Lana shared a kiss and I wondered if that was the first time they ever kissed. I rolled to my right and lay on top of Cathy. Her body was very round, so I rested my weight on my hands on the floor near each side of her arms. I gave her a very passionate open mouth kiss and then started licking and sucking her enormous left breast and nipple. Lana joined in and did the same to Cathy’s right nipple and tit. Lana and I shared a kiss in between breaks of attacking Cathy’s huge rack.

I slid my hand down Cathy’s stomach and down to her pussy. I started rubbing her clit and Lana followed my lead. She started licking Cathy’s clit while I started inserting my index finger into her pussy. Lana was going crazy licking Cathy’s love hole and I stepped back and watched for a second or two. An idea struck me and I left our love triangle and went to the kitchen. I came back with a dish towel. I went over to the coffee table, now located in the corner of the room and started cutting up some coke.

Cathy and Lana switched into a 69 position. It was so cool! Their body’s so different, but enjoying each other as their tongues were licking the cunt of one another. Wow, this was a hot night!

I lit a cigarette, licked my finger and then ran my moist finger around the cigarette just above the “cherry”. I picked up a pinch of the cocaine and sprinkled it on the moist part of the cigarette. I handed the smoke to Lana and told her to take a hit. She dragged on the cigarette and the cocaine started to bubble and glow. I created a version of a crack hit and Lana took it in deeply. Before she had a chance to exhale, I put my mouth in front of hers and as she exhaled, she blew the smoke in my mouth. I treated the cigarette for Cathy and she exhaled into Lana. For the last hit of the cigarette coke treat I inhaled it and exhaled into Lana.

We were all having the best times of our lives; well at least I know I was having mine. But when looking at Cathy and Lana, I knew they were also having the time of their life. It was time to get back down into the action, so I led Cathy down on her back and I lay down on my side beside her. I kissed her deeply and stuck my hands between her legs and found her wet pussy. She guided my index finger into her pussy and I began to finger fuck her pussy.

Lana took the initiative to go to the kitchen and fill our drinks. Cathy whispered into my ear “This has never happened before. I have never been with Lana and a guy, I mean I have never been with Lana, I mean”.

“Relax, Cathy. Let’s just party, ok?” I said

Cathy smiled and said “Then get back to fucking me, Tony.”

Cathy was almost laughing when she said this, but two seconds later she was gasping as I inserted my index and middle finger in her pussy. I went down lower so that I could lick Cathy’s clit as I fingered her. Then I stuck my hard cock in her pussy and started fucking Cathy really hard. She was meeting my thrusts with her hips and my cock was buried in her pussy. I took out my dick as Lana returned as we were all dying of thirst.

We were all taking slurps of our drinks and I wiped down Cathy’s huge belly with the dish towel and laid out two lines of cocaine on her belly. Lana and I inhaled the lines off her stomach and then Cathy did a line off of Lana’s ass. I told Cathy to roll over and get on all fours. Lana spread out in front of Cathy and Cathy lowered her upper body so that she could eat Lana’s pussy. At the same time, I started fingering Cathy again and slid my index and middle finger in her pussy. As she ate Lana out, I spread Cathy’s pussy wide open and inserted my ring finger and eventually my pinky in her pussy.

Lana was cumming again and as she moaned I told her to come back with me. I took Lana’s hand and replaced my hand with hers; she started sliding her four fingers in Cathy’s pussy. Cathy was bucking back wildly.

“Oh, Fuck! That feels so fucking good.” Cathy moaned.

I told Lana to get her thumb inside as well and she slid it in Cathy’s wet pussy. Her hand was much smaller than mine and she started to slide her hand in deeper and deeper.

Cathy rolled onto her back and said “Lana, I want you to fist fuck me! Shove your fucking fist in my cunt.”

Lana reinserted her fingers and then her thumb and soon her whole hand disappeared into Cathy’s cunt. She started slowly shoving it in her pussy so that her hand up to her wrist would vanish into Cathy’s pussy. Cathy started to shake and scream with ecstasy as she had a mind boggling orgasm.

“Oh, oh, oh, oh, oh, oh my God”. Cathy screamed over and over. “I am still cumming!”

Lana pulled out her fist and had the biggest smile on her face. I crawled up to Cathy’s face and put my dick in front of her. Cathy eagerly took it in her mouth and I started fucking her mouth.

“Fuck my cock, Cathy.” I said. “I am going to shove it your mouth so fucking hard and I want you to swallow my whole load of cum.”

Cathy was more than eager and I really started pounding my cock into her mouth. Her mouth was so eager and I loved the feeling. I slowed down the pace and Lana came over and started licking my ass and feeling my balls.

“Don’t shoot inside her, I want you to shoot your cum all over my tits and have Cathy lick all your goo off my tits.”

It was not five seconds later that I pulled my dick out of Cathy’s mouth and shot the biggest load of cum I could ever remember all over Lana’s beautiful rack. Cathy immediately rolled over and licked up the entire load of cum off her nipples, tits and the space between her massive jugs.

I don’t remember much of the evening after that; I know we stopped doing the coke and I ended up spending the night, sleeping in Lana’s bed. I woke up the next morning around 9:00 and realized I was sleeping next to Lana. I kissed her gently on the cheek and she gradually woke up. We made love that morning very gently and slowly as we were both a little hung over, but horny. She kissed me good bye and my Saturday morning was off to a fine start.

Chapter 8: Tango Anyone?

Saturday morning was kind of a foggy reality. I remember driving home from Cathy and Lana’s place and taking a nap in my own bed. I woke up around 11 AM and felt awesome. I love long weekends as they provide time to party and more importantly time to recover from the partying. I got out of bed, did my duties in the bathroom and walked into my kitchen. As I prepared a pot of coffee, I noticed my message light was flashing on my phone message machine.

As the coffee was brewing I walked to my answering machine and pressed the play button to hear the waiting message.

“Hi Tony, this is Glenn. I am the owner of Tango’s and we met last night. When you have a minute give me a call back at my house. John and my number is 555-4627. Hope to hear from you soon.”

The message made me feel a little awkward. I wondered how Glenn got my phone number. Maybe he called information and requested my number. But why would he want my phone number. I waited for my coffee to brew and proceeded to pour a cup of black coffee. I sat at my dining room table and picked up my wireless phone and called Glenn’s number. The phone rang twice before an unfamiliar male voice answered.

“Hello.” The voice said.

“Hi, is this Glenn and John’s house?” I asked.

“Yes, this is John, who is this?” a very pleasant voice asked.

I thought out for a second what I should say then “I am Tony, I met Glenn last night and he left me a message on my machine to call him.”

“Oh, you are Tony. Glenn told me about you. I can’t wait to meet you. Glenn was hoping you could come by and have a drink tonight, but let me have him explain. Can he call you back?”

“Sure.” I replied. “I will be home for a while, have him call me.”

“He should be back soon.” John said.

John and I chatted for a few more seconds and then we hung up. I really thought this was strange. Why did Glenn call me? Why did John know about me? Why did Glenn want me to come by his house tonight? What did I talk to Glenn about last night that prompted him to call?

I finished my coffee and waited for Glenn’s call. About noon the phone rang and Glenn was on the other side. We exchanged pleasantries and he gradually led into the subject of why he called.

“Tony, I am going to be direct and I hope you do not take offense to my questions. In fact, I hope you are excited about the questions.” He said.

Now my mind was going a million miles an hour and I had no idea what direction Glenn was headed.

“Go on.” I replied. “I am sure I won’t be offended, but I have no idea what you are going to ask.”

Glenn proceeded on to tell me about the previous evening at Tango’s and how he enjoyed our conversations during the evening. I guess I was pretty drunk as I didn’t remember all the details of our conversations. He thought I would like to come over to his place tonight and we could talk more about Tango’s and my interest in cross dressing. When I asked him why he felt I had an interest in cross dressing, he said I brought up the subject on three occasions last night.

“Tony, I hope I am not off target, but I think I can read people pretty well, especially when it comes to the subject of femininity in guys. I don’t know if you are gay, but I certainly saw a light in your eye and genuine curiosity when we talked about cross dressing.” Glenn said. “Tony, I know you either have or are seriously considering it, right?”

“Well, even if I did, what does that have to do with me coming over tonight?” I asked.

“It depends on what mood you are in. If you just want to come over and visit, I am having a few friends over for drinks and then going over to Tango’s later. It will be busy there tonight, so I have to spend a few hours at the bar and everyone at my house will want to come too.” He said.

I didn’t reply right away, so Glenn continued. “If you are in for a more crazy night, you might be able to have some fun, either by coming over ‘dressed’ or bring your other wardrobe with you and change here if you feel comfortable.”

My heart was kind of in my throat. This was the first person who had guessed that I was a cross dresser and I was unsure how to react. I didn’t answer again and Glenn said. “Tony, it is ok. There are lots of people like you. Straight, Gay, Bi, whatever, that like to cross dress.”

“I am not sure, Glenn. I will come over, but I am not sure what I am going to do when I get there.” I replied.

“Awesome, you will have a great time, I hope you aren’t too hung over from last night.” He said.

Glenn filled me in on where he lived and gave me directions. He said his friends would arrive around 8:30 PM and leave for Tango’s around 9:30 or 10:00. I was welcome to come over early around 6 or 7, if I wanted some time to get to know John and himself better.

I fiddled around most of the afternoon, watching football, and running errands. I made sure to water Sheila’s plants and then it was about 3:30 and I had avoided the subject of going to Glenn’s all day. Anytime a thought went into my mind on the subject, I quickly tuned it out. I knew I had to go, since I committed, but I was unsure if I should bring an outfit with me. For some reason, I really trusted Glenn, even though we had just met. He was so reassuring on the phone and he was very mature, not pushy and he obviously trusted me immediately (by selling us the coke the night before).

Around 4 PM, I stepped into the shower and thoroughly cleaned up. I shaved my legs, arms, chest and removed the rest of my under arm hair. I cleaned up by shaving around my balls, crotch and butt. I decided if I was going to go through with this, I was going to do it right. I packed a duffel bag with all of my supplies. I must have gone over the list four times to be sure I had everything I needed.

I left my house around 5 PM and stopped off at a nail salon. I proceeded to have the first manicure of my life. It felt great and it made my nails look much more presentable. I was out by 5:45 and finished the short drive over to Glenn’s house.

They lived in a small house in an old neighborhood section of Pasadena. It was only a short drive to Tango’s and was only minutes from some of the most expensive real estate in Southern California. I pulled up to the curb in front of their house and parked my Chevy rental van under a tree that hung over the street from their front yard.

I was quite nervous as I walked up to the door with my duffel bag over my left shoulder and a bottle of wine in my right hand. Before I could ring the bell, the front door and screen door opened and Glenn was waving me inside.

He thanked me for coming, for bringing the wine and told me to relax and motioned me over to the living room where there were several chairs and a large sofa. I sat in one of the armchairs and Glenn sat on the couch. The room was beautifully decorated with a Persian rug and antique tables, yet it still looked very modern and extremely comfortable.

John strolled in the room two minutes later with two perfectly prepared Rum and Cokes (in a bucket) in his hands. I stood up to meet him and after placing down the drinks, he shook my hand and then gave me a hug. “I am so glad you came over.” John said.

He immediately made me feel at ease. John reminded me of someone I knew. He was about 35 (about 20 years younger than Glenn) and about my height. He was not feminine and I would have never would have suspected he was gay if I would have met him elsewhere. Glenn, John and I talked for about 15 minutes as John and I finished our drinks and Glenn prepared us refills. We were drinking (Glenn was sipping a beer, as he had to stay sober until we got to Tango’s) and smoking and enjoying the conversation.

I learned that John was a manager of a salon in the Galleria in Glendale (about 20 minutes from Pasadena). The Galleria was the nicest shopping center in this part of Southern California and this was the nicest salon at the Galleria. He had known Glenn for ten years and they had been together the past eight, the last five in Pasadena.

The subject changed to cross dressing somewhere between the third and fourth drink. John told me that he had been cross dressing since he was eight years old. He has always only done it for fun, not sexual kicks, and that Glenn thought it was fantastic when he would dress up for parties or Halloween. He asked about my experience and I told him that I had only just started and I was totally in the closet about the situation. He and Glenn were the first people to know about my secret.

Glenn told me they had about six people coming over tonight. They were going to arrive in about 90 minutes. Five of them were gay friends and the sixth was a brother of one of the gay friends visiting from out of town. John told me that he would love it if I dressed up tonight and if it made me feel more comfortable, he would also. They asked if I could be ready in an hour and a half.

I replied. “Sure it won’t take me that long to get ready, but I am not sure if I should do this.”

“Please.” John said. “I will get ready in our bedroom, you can have the guest bedroom, it has its own bathroom. I will come visit you in about 45 minutes and help you with your make up and hair.”

“Ok.” I said. “I can’t tell you how nervous I am.”

But a few minutes later, I was laying out all of my clothes, accessories and the rest of my items on the queen size bed in the guest room. About ten minutes later, Glenn knocked on my door and brought me a fresh drink. I told him to keep them coming, I was going to need the courage.

John came in when I was 95% done. All that was left was for me to buckle my belt and slip on my shoes. He looked fantastic! I would never have known it was him. He looked like Deborah Winger, the movie star. She was dressed in a very short plaid skirt with white ankle socks and black patent pumps. Her blouse was a white collared shirt that was tied into a not at the waist. It was school girl gone bad.

“Wow, John, you look remarkable.” Without realizing it, I said this in my feminine voice.

“I am sorry.” He replied. “Have we met? My name is Julie, not John.”

“My mistake, Julie. Nice to meet you, I am Cassandra, but call me Sandy.” I said as I gently shook the hand being offered by Julie.

“My friends call me Jules”. She replied.

Jules was carrying treats. She laid out two big lines of cocaine on a mirror on the dresser. We inhaled the lines and Jules helped me re-do some of my make up. She also touched up my nails, let me borrow some other items and had me looking twice as good as usual.

“Sandy, you are one hot little slut.” She said. “You like wearing the sexy slutty outfits, don’t you?”

She leaned over and kissed me on the lips. Oops, we will have to re-do our lipstick. We touched up and then walked into the living room to see Glenn. He was busy putting snacks out on the dining room table and turned to see us.

“Jules, how good to see you. You look extremely hot tonight and who is your beautiful friend?” Glenn was a good actor.

“Thank you Glenn, this is Sandy.” Jules said.

Glenn walked up to me and said. “If I was straight, I would be all over you. I would never know you were a guy, especially if I was drinking.” He kissed me on the cheek and gently rubbed the cheek of my ass through my tight dress.

When I was packing my clothes, I was unsure what outfit to wear, as I have been constantly picking up more items. I was wearing a long sleeve short black patent dress that featured asymmetrical straps and silver buckles and zippers. It was pretty close to skin tight and I had unbuttoned the top two buttons. I wore white fishnet tights and black patent high heel pumps. Silver jewelry including anklets, bracelets, necklaces, earrings and some rings that John, I mean Jules, loaned me. Bright red lipstick and nails finished off the look. The dress was so tight and so short, I wasn’t sure how I was going to sit, but on a barstool, I would be ok.

Glenn gave me another drink and the three of us did a line. Glenn explained that he only did everything in moderation, but not to worry, when he was our age he partied extensively and wanted us to have fun. Jules came over to me and kissed me on the lips again and Glenn explained not to worry about that either, they had a total open relationship.

Glenn took several pictures of us together and each time we were close to one another Jules would get more aggressive with the kissing and touching. We had a cigarette and Glenn told us that Bruce, Mark, Dennis and Leon were on their way and would be here any minute. Frank and his brother Lee were going to meet us at Tango’s as Lee’s flight was late and Frank was at the airport picking him up.

They briefly told me about the guys arriving and told me that Lee was a very nice straight guy that lived in Sacramento and came down a lot to visit his brother and other friends in Southern California. Frank was very rich, so Lee would come down and stay at his brothers’ house while he partied in Southern California. Frank called Lee, the Sacramento stud as he always got laid when visiting. Bruce and Mark had been dating for about three months and they met at Tango’s. Dennis was a friend of John’s from work and his partner was Leon. It was hard to keep all of this straight as the drinks had been piling up and even with a couple lines of coke, I was pretty smashed.

The guys arrived together a couple of minutes after 8 PM. They were all very nice guys. Glenn introduced us to everyone as Julie (call her Jules) and Cassandra (call her Sandy). He told them we were lesbians but also like to have a little fling now and then with guys. Everyone laughed as Jules came over and gave me a big kiss on the lips and slipped her hand under my dress onto my ass.

Jules whispered in my ear. “You have me so hot! If you come back here tonight, you will have to fight me off, te hee.”

I was not sure if she was serious, but I was having too much fun to think of what that meant. I felt so feminine in my clothes and my surroundings I was really thinking of myself as a woman and did not have a concern in the world. I walked over to Glenn and thanked him for doing this and inviting me. He was so happy that I was comfortable and having fun.

A few minutes later I dropped my bag with my men’s clothes in the back of my van and hopped in the car with Leon, Dennis and Jules, Jules and I sat in the back seat. We passed around a bullet to take some cocaine hits and I felt Jules hand on my left side. We arrived at Tango’s around 9:30 and Glenn was already behind the bar finding out how things were going.

From my perspective things were busy. Almost all the bar stools were taken, but Glenn had arranged two pub style tables at the end of the bar with stools all around. He motioned to me and Jules to take a seat at one of the tables and served us a couple more rum and cokes. I told him that I would switch to Scotch on the next round and Jules said she would change to a Vodka Martini.

The place was rocking, a band was warming up and there was a big crowd of people surrounding the small dance floor at the very end of the large room. I was very excited, as this was the first time I had really been to a public place as Sandy.

Jules was talking to Leon, when two guys approached our table. The men were dressed to the ‘nines’. One guy was in a beautiful grey suit with a white shirt and red striped tie. The other man was a few years younger and dressed in a black sports coat with a grey turtle neck sweater and dark grey slacks. Obviously these guys were Frank (who looked to be around 30) and Lee (probably 25).

The older of the two looked at Jules and I and said “Hi, I am Frank and this is Lee. What are two beauties like you hanging around these ugly old faggots?”

I had to admit this caught me totally off guard, but laughed hysterically as did anyone close enough to hear. Glenn walked over laughing so hard he was almost out of breath. Frank had never seen John dressed up and I am not sure he knew who she was until Glenn introduced us formally.

Lee was extremely handsome and I could see why he did so well with the ladies. He kissed my hand when introduced and offered to buy me a drink. I accepted, but before drinking it, Jules grabbed me and pulled me out to the small dance floor to dance. Jules explained to me the band played great 80’s songs, especially new wave dance songs. We were immediately hopping on the floor together to a version of the Romantics “What I Like About You.” We danced for two or three songs and then returned to the tables.

We drank a couple glasses of water and then the bartender appeared with a martini and a scotch. Glenn had joined us at the tables and they were a happy group of guys and obviously getting drunk. Lee was probably the furthest along as he had been drinking for about four hours at Sacramento Airport. He was very attentative to me; I realized that he did not know I was a guy.

I grabbed my handbag and went to the restroom. Glenn told me to use the ladies room. I fixed my make up and lipstick and looked in the mirror. Jules appeared a moment later and helped me primp.

“I don’t think anyone told Lee that you were a cross dresser.” She said.

“I know, I have to tell him, he would hate me if I didn’t.” I replied.

We both laughed and returned to the table. Lee was chatting with me and I asked him if he would like to step outside for a breath of fresh air. He agreed and we left through a back door that went to a side parking lot where we had parked.

“Do you like to party, Sandy?” Lee asked as we stepped outside.

“Of course I do. But I have something to tell you first.” I said.

“Follow me, you can tell me in a minute.” Lee replied.

He grabbed my hand and led me over to a van parked in the lot. This must have been Frank’s van, as Lee had the keys. He opened the passenger door and reached in to slide the big side door open. He closed the front door and stepped into the van and I followed him. It was huge, like a cargo van, but was set up like a small business office in the rear. The back section had a round table with swivel chairs mounted to the floor. I was very surprised by this appearance, so he explained that Frank owns a consultant business on construction and architecture. He was always on the road to sites and would hold meetings in his van. This one was brand new and had lots of features including a car phone. He turned on a couple of lamps that were obviously mounted to a cabinet that appeared to hold paper work.

When I sat at one of the chairs, Lee asked. “I don’t suppose you like to smoke crack?”

“Ooh, you asked the right girl, I love it!” I said. “But Lee, I have to tell you something, I am not your usual girl.”

“What do you mean? You mean you don’t put out on the first date?” He laughed.

He was in the process of loading a beautiful big rock of crack into a glass pipe. He looked at me and said “Are you going to tell me you are a guy? Because if you are, you don’t need to say anything, let’s just see what happens, ok?

“Sure baby, let me have the first hit and come sit right next to me.” I said.

I remembered my evening in New York with Linda and the trick she showed me with the crack. I took a huge pull and watched the glow of the rock as it ignited fully. I felt the warm smoke enter my lungs and then I held it in. I moved over and straddled Lee on his chair hiking my dress all the way to my crotch. I gently kissed his lips and motioned his lips open and then I slowly exhaled the entire hit into his lungs. Lee took in the whole hit and then exhaled himself. I slid the pipe between his lips and lit the glass pipe and rock for him. As he exhaled his powerful hit I kissed him on the lips and he eagerly stuck his tongue in my mouth. I slid further up on his lap and could feel his cock getting very hard.

I slid off of Lee and knelt before him. I spread open his sport coat and undid the belt to his grey trousers. I unbuttoned his pants, unzipped his fly and pulled down his pants below his knees. I could see the top of his cock sticking out of his bikini briefs and it was very hard. He slipped off his left shoe with his opposite foot and repeated the process on his right side. I wasted no time and slid his briefs down all the way to his ankles and slid his trousers and briefs all the way down and over his feet.

His cock was standing straight up and it was a nice specimen of a piece of the male anatomy I was becoming more familiar with. It was about six to seven inches long with a purple colored head. I reached out had put my right hand around the base and started with a very deep plunge with my mouth down the entire length of his cock. I could feel the head of his dick hit my throat and I was able to take the full shaft all the way so I could lick the base of his cock while having the full length in me. I slid my mouth up his rigid shaft and ran my tongue along the underside of Lee’s cock.

I moaned in a very sexy manner as I went down the second time on his dick. Lee pushed my head down so I was all the way down on his cock and I gladly took it deep into my throat. I heard a knock on the door and heard it slide open and out of the corner of my eye I saw Frank step in the van. I looked up at Lee while I came up on his cock and he had a smile on his face.

“I thought I would find you two in here, but not doing that!” Frank said.

Frank strode over and sat in the chair I had just left. He undid his belt and took his pants down as I licked and kissed Lee’s balls. Obviously Frank wanted to play too; I was getting very excited as I was about to service two very handsome men.

As I took another plunge down Lee’s cock, I looked up into his eyes to see how he was reacting to his brother joining us. The look in his eyes and face was pure ecstasy; he was totally into enjoying the blow job I was giving him. Without even looking in Frank’s direction, I stuck out my left hand and felt for his cock. I grabbed it around the base and started stroking his dick as I went down on Lee’s cock again all the way to the base. Lee was already moaning like he was going to come and as I stoked Frank’s cock up and down I felt Lee ready to blow in my mouth.

“Fuck! Sandy, I am going to cum! Suck my cock and drink my cum!” He roared.

He started moaning louder and I felt his jizz hit my throat and I could taste the sweet flavor of his cum. I was eager to swallow every last drop as it tasted wonderful and it made feel like the slut I wanted to become.

“Fuck! Frank, I have had blow jobs, but this bitch is the best I have ever had. She sucks cock like no one else.” Lee said.

I was just removing my mouth from his cock and came up to greet him with a big kiss. The entire time I was doing this, my hand never left Frank’s cock. I finally turned around and looked at Frank. He was very handsome and I was very anxious to suck his cock as well. I turned my attention to his “member” and saw that it was smaller than his little brothers, but still very nice. It was about 5-6 inches long and getting harder with every stroke from my hand.

“Well little brother, I may let this little slut suck my dick, but I think I am going to fuck her.” He said. “How about you reload that pipe?”

Lee immediately started to reload the pipe and I started working Frank’s cock in my mouth. I did my deep plunge and took his whole cock in my mouth on the first try. Then I started to lick and play with his balls. I sucked each of his balls one at a time and then lifted his ass of the seat and licked his ass as well. Then back on his cock and did about 20 or 30 sucks on his cock going as fast as I could and moaning frequently.

“Frank, I love your cock, I love sucking your dick.” I said in between going down on him.

At this point Lee handed me the pipe and I stopped sucking Frank’s dick. I put the pipe in my mouth and Lee lit the pipe, it glowed and crackled and I took a deep hit, but did not hold it, I pulled Frank close and exhaled into his mouth to give him an extra deep hit. Then I inhaled again and did the same to Lee. Lee reloaded the pipe and we all took big hits individually.

I was so fucking high and horny, that I started again on Frank’s cock, which was still very hard. I went up and down with my mouth on his cock so fast, that it was like a wood pecker pecking a tree. I was very gentle as I always opened my mouth wide going down and sucked his rod very tight on the way up. I was licking his shaft every time I rose up on his cock and was also kissing his balls and licking his asshole in between my deep plunges.

Frank was hard as a rock (and I think Lee was hard again from watching) and I knew what needed to be done. I stopped sucking his cock and went to my handbag and pulled out some lubricated condoms and some KY jelly. I slipped off my shoes and pulled down my fishnet tights and slipped them off my right foot.

Next I opened up a condom packet and removed a rubber. I placed it on Frank’s cock and sucked it a little to keep him hard. I didn’t have to do anything else, as Frank took charge. He stood up and leaned me over the table and lifted up my skirt. He slid the strap to my thong panties out of the crack of my ass exposing my puckered asshole.

“Lee, lube her up, put some KY on your finger and stick it up her ass. Be gentle, work it in gradually.” Frank directed.

Soon I could feel the lubricant being applied to my ass and then Lee’s finger going inside me gently. I was moaning in ecstasy as soon as his finger penetrated my asshole. Lee was so gentle, but at the same time he was getting more aggressive. He worked his index finger deeper into my ass as I moaned with excitement.

“Good job bro. Let me tap that ass now. Frank said.

I felt Frank put his cock up against my ass and spread my cheeks apart. He guided his cock so that it was in the center of my asshole and I could feel him apply pressure on my tight ass. His cock went in much easier than I thought and in seconds he was all the way in.

“Oh baby, Frank, I love your cock inside me. It feels so good, fuck my ass, Frank.” I said.

I loved the feel of his dick inside and I was practically begging him to start fucking me. Frank pulled his hips back so that his cock almost left me then slid it back in very slowly.

It felt unbelievably good. Frank repeated this about four times and I could tell he was very excited.

“Oh, Sandy, you feel good. What a tight fucking pussy you have. Damn, you are good.” Frank commented.

He started to fuck me faster and harder. After two or three plunges, I felt the rhythm of his cock pounding my ass and I started to meet his thrusts. I was shoving my ass towards his cock, so that I could feel the full length of his cock inside me.

“Come on baby, fuck me hard! I want your cock in me all the way. Yea, baby fuck me fuck my brains out.” I was practically moaning my words as I was in one of the highest levels of pleasure I ever felt. “Fuck me harder.”

Frank was pounding inside me faster and harder and I could not get enough. I was practically throwing my ass towards his cock to get more and more of him.

“Sandy, I am going to cum so hard.” He said.

“I want to drink all of your cum.” I said.

He pulled out of my “pussy” and I turned around and immediately went down on my knees in front of Frank. I pulled off his rubber and took his cock in my mouth and gave him the fast up and down treatment on his cock. He was ready to blow his load and I could not wait. He shot a strong load of cum in my mouth and I slurped off each last drop. I licked every last drop off his cock and cleaned his balls with a very sensitive tongue bath.

I barely noticed Lee beside us stroking his cock and it was hard again. I wasted no time and scooted over to him and took him in my mouth. I spent the next five minutes repeating my blow job on Lee and felt him getting ready to blow again.

“Sandy, I want to fuck your pussy too!” Lee said.

I leaned over the table as Lee placed a condom on his cock and Frank put a little more KY on my asshole. Lee didn’t waste any time he gave me a very powerful thrust and shoved his cock all the way in my ass on the first shot. I screamed in ecstasy.

“Yes! Yes! Yes! Fuck me Lee, fuck me hard.” I screamed again.

Unfortunately he was so fucking hard it only took two or three long hard thrusts and he came.

“Fuck, Sandy. You have the tightest ass I ever felt. I didn’t stand a chance.” Lee said as he pulled his cock and soiled condom out of my ass.

I turned around and looked at my two latest lovers. I couldn’t believe what I had just done, but could not have felt better. I straightened out my panties, put my tights back on and tried my best to get myself back together. We each took another hit off the pipe and I left the van first and returned to Tango’s. I went to the bathroom to get fixed up and soon Jules was there wanting to know if I would tell her what had happened.

“Girls aren’t supposed to kiss and tell are they?” I asked with a big laugh.

“Well, you can always share with your best girl friend.” She replied with a wink.

We agreed to catch up next week and to get back out to the bar and have a drink and dance some more. It was a great night of drinking, dancing dressing and fucking. I had the time of my life on my first time “out” as a girl. I couldn’t wait for my next adventure. I told my friends that I was tired and Glenn offered for me to spend the night at his house. I declined and told him I would pick up my van tomorrow.

Glenn called me a cab and about fifteen minutes later the bartender told me that my car was here. I kissed all my new friends good night and walked outside to the cab.

I hopped in the back seat of the cab and gave the driver the address to my apartment. It was only a ten minute cab ride to my place and we were half way there when he spoke. “So did you enjoy yourself tonight?” The driver asked.

“I had a great time, but had a little too much to drink, so I needed a cab.” I replied.

I really couldn’t see him or what he looked like, but I could tell he was about 60 years old with dark skin and his voice had a Middle Eastern or maybe an Indian accent. I was not looking to be a conversationalist as I was really ready to go home and rest.

“Very smart.” He replied. “Very smart not to drive when you are drunk. The police are very tough in this town, especially on beautiful women like you. They would pull you over and don’t know what would happen.”

“Well, I can take care of myself.” I said in a very meek voice. “I bet you get a lot of action on Saturday nights.” I don’t know why I said this, but I felt exhilarated all of a sudden.

“What do you mean?” he asked.

“Well, girls like me get a ride home in a cab after getting all drunk. I mean I get so horny when I drink, I bet you get girls all the time.” I said.

“Not very often.” He replied. “I wish I got lucky more often.”

At this point we were nearing my complex and I instructed him to pull up to the garage. I had a key on my key chain that opened the door to the garage. The lock was accessible from the car, so he pulled up to the lock and I rolled down my window and opened the garage. He pulled in the garage and I told him to park in my spot.

I opened up the car door stepped out and walked up to his car window. “I am going to give you an option, driver. You can have $10 for the ride or you can come upstairs and I will give you a blow job. What would you prefer? I asked.

He could not get out of the car any faster. I got a good look at him now and he was at least 60 and was very heavy, probably 250 pounds. I grabbed his hands and led upstairs to the pool area. I told him to stand by a chair and I unbuckled his belt pulled down his pants. I told him to sit in the chair and then I started sucking his already hard cock. It was a small cock about the same size as mine, but it made it very easy to go all the way down on him. He was shoving my head down with his hands when he shot his load in my mouth. I slurped up every drop.

“Thanks for the ride!” I said.

I walked away as he was still buckling his pants and belt. “Thank you, honey! That was great!” He said as I walked through the opposite doorway.

I walked down to my apartment and let myself in. I went to my full length mirror and was amazed that I still looked pretty good. I mean I had sucked three cocks taken two up the ass, danced, drank and I could still pull off looking pretty good.

I undressed and didn’t bother to shower. I was asleep in no time at all.