Life was becoming a little confusing. I was out of high school and attending the local community college part-time at night while I worked at the machine shop during the day. I played soccer on the college team in the inter-county conference. Mom helped me buy a nice used car. Still, I wore panties, a bra, and nightshirt to bed every night. Sis was working part-time at a hairdresser while taking cosmetology courses in the evening. We still sat together in our panties and nightshirts occasionally before bedtime talking about our personal issues. She was still having girls over and giving me a free show now and then. I had not tried to have sex with a girl since my two failures last year and jerked off to porn in my nightwear to keep myself satisfied for now.

On one of my jerk-off-to-porn nights, I found this gorgeous, sexy, hot woman sucking this well-hung stud. When his dick was full of her slobber, she climbed on top of him, pulled her panties down below her ass, and started to sit on his dick. It was the hottest thing I'd ever seen. As his dick began to push into her ass, the camera moved to her face. She started out with an expression of pain and apprehension, followed by a look of relief, followed by a look of passionate pleasure that was indescribable. She raised her hands to the back of her head and lifted her hair up. Her eyes were almost shut and her lips were pursed into a small circle as she slowly exhaled. I came like a horse in my panties.

The camera started panning back showing her body sitting on the stud’s dick. She was beautiful. Then came the unbelievable--she was a he. She had all the features of a real woman: pretty face, long hair, real breasts, round ass. But, she had a six or seven-inch dick that was now sticking out of the top of her panties. The stud began jerking her off until she came all over his bare stomach. She then leaned forward until his dick came out of her ass. She was dripping come out of her ass. Finally, she got up, leaned over him, and licked her come off his stomach. My panties were completely soaked with my come. I turned off the computer and fell asleep with the whole episode playing over in my mind.

The next few weeks I couldn’t get enough of “T-girls.” I was actually coming some nights without even jerking off as I watched them. I had to go to Sis’s room two or three times a week to get clean panties. As the panty drawer was getting low I started to check some of her other drawers. That’s when I looked in her night table drawer. She had a collection of vibrators and dildos. One of the dildos had a large suction cup on the bottom. Since she told me I could come to her room for anything anytime, I didn’t think she would mind me borrowing it.

I took it into the bathroom and stuck it on the bottom of the bathtub. Then I stepped into the tub, pulled my panties down below my ass, and started to lower myself on the dildo. As the end started to push against my asshole I felt an unbearable pain and burning. This wasn’t going to work.

I went back to Sis’s bedroom and got a small vibrator. Then I remembered some of the videos where the guy would use lubrication first. I got some petroleum jelly from the medicine cabinet and rubbed it on the vibrator. This time I held the vibrator on the top of the closed toilet lid and lowered myself on the vibrator as I straddled the toilet. As it started to enter my ass I could feel the small nubs on it. The combination of the smaller diameter and lubrication allowed it to push in with no pain. However, it felt like I was taking a dump in reverse. While it felt strange, my little dick was completely hard and oozing precum.

As I was holding the base I inadvertently started the vibrator. At first, it took me by surprise, but within a minute or two I was coming all over the place. I was in ecstasy. I pulled it out and washed it off. Then I put the vibrator and dildo back in Sis’s drawer exactly as they were. I kept my cum drenched panties on, cleaned up the bathroom, and went to bed.

On Wednesday nights I got done my night classes early and got home well before Sis. So every Wednesday night I would visit her night table drawer. One of my favorite vibrators was her “silver bullet.” It was about four inches long, hard, slim, and had a wire with a remote control. I decided to keep it for the night a few times. I could slip it into my ass, lie on my stomach, and then turn it on while watching porn on the computer until I came in my panties. I often fell asleep with the vibrator still in my ass. When that happened, I would clean it in the morning and put it back as soon as Sis left before I went to work.

Eventually, I felt I was ready to try the dildo with the suction cup, again. So one Wednesday night I got it from the night table and stuck it on the bottom of the bathtub. This time I lubricated it with baby oil first. Then I stood in the bathtub, pulled my panties down a little, and began to lower myself on the dildo. As I made contact with it I could feel my hole being forced open and a slight burning. I positioned myself so my knees were on the tub floor and I could control my descent.

I felt just like the T-girl in the porn video. As the head of the dildo penetrated my sphincter, there was a brief pain followed by an immense pleasure as I could feel the shaft slowly sliding up my ass. I had to put my arms up and wrap them around the back of my head. When I felt my cheeks touch the tub floor, I was disappointed that it was in as far as it could go. I was oozing precum and my whole ass was warm inside. Then I raised myself a little and I felt like I was taking a dump. Then I lowered myself, again, and felt that wonderful feeling all over another time. I started moving up and down, fucking the dildo.

Before I knew it I was coming like never before. In fact, I was becoming a little dizzy like I was drinking alcohol. When I finally raised myself off the dildo I had a sudden empty feeling in my ass. I could feel the baby oil between my cheeks and a tingling inside. I pulled up my panties. I lost track of the time and quickly pulled up the dildo to wash it off. I quickly washed it with soap and water, then returned it to Sis’s drawer. Every step I took as I walked to her bedroom and back to mine felt wonderful. I went to bed with my wet panties on and a little tingle in my ass as I fell fast asleep.

One night when Sis and I were on the couch talking she asked if I would like to go to a Halloween party at the house of one of her friends. “It would be a chance to go out dressed like a woman without anyone thinking much of it,” she suggested. “It will be fun and no one there really knows us anyway.”

I wasn’t sure what to think. It could make my life more confusing or it could help me decide where I wanted to go with things. I asked Sis, “What will you wear?”

After thinking a few minutes she responded, “We’ll go as Two Broke Girls like on the television show.”

“Okay,” I said, “Let’s do it.” I felt better about the idea, knowing she would be close by me as the other half of a duo. She said we could try on some outfits on Friday night for the party, which was on Saturday night. I spent the rest of the week watching reruns of the television show so I could imitate my character.

When I got home on Friday night, Sis already had a bunch of outfits on her bed ready for me to try on. As I took off my shirt and pants she handed me a bra, panties, and a pair of silicon breasts. She detected my discomfort so she held the bra out, helped me into it, and hooked it. Then she tucked the fake boobs into the bra and adjusted them. I took off my briefs and put on the panties. Next, she pulled a dress over my head and down until it was in place. The buttons were on the top half in the front. She buttoned the bottom four or five and left the top three open leaving a little bit of the bra exposed. I couldn’t believe how good I looked in it.

Sis said, “This could be the dress, but let’s try a few more on before we decide.”

We spent the next hour trying different dresses on me. Finally, we decided on the first dress since it not only looked good but was similar to what was worn on the show. Sis told me to make sure I was home by six so we had at least two hours to get ready for the 9:00 pm party. It seemed like a long time to dress, but I agreed I would be home as she requested.

The next day I had a soccer game at noon and Mom was away for the weekend. The game was over by two, so I went straight home afterward. Sis was doing the laundry when I came into the house. She said our dresses were still in the washer and were not ready yet. Since it was early and Mom was away she told me she would get me a bath ready in Mom’s big bathtub.

Twenty minutes later she called me into Mom’s bathroom. She said, “Strip off all of your clothes.” When I hesitated, she responded with, “You’re wasting time, you don’t have anything I haven’t already seen.” With that, I took off all of my clothes. Then she opened a plastic bottle of Nair hair remover.

I said, “What are you going to do with that?”

Her response was, “Get rid of your body fuzz. Nobody likes a hairy girl." She squeezed some of the lotion in her hands and rubbed it on my legs first, then on my arms, and lastly my chest and stomach. Next, she told me to hold my arms up while she lathered my armpits and shaved them. Then she took a wet washcloth and wiped the hair remover off. She showed me the hair that came off as she wiped. When she was done wiping she told me to step into the tub and relax while she did another load of laundry. The bath was warm and smelled like flowers. I felt like I could fall asleep, it was so relaxing.

After an hour or so, Sis came in and said it was time to get out of the tub. She gave me a towel to dry off. When I finished drying she wrapped the towel around me and tucked it in at the top. Then we walked down to the kitchen where she had me sit on a stool and lean back into the kitchen sink where she could wash my hair with the rinsing hose. She used another towel to dry my hair somewhat before taking me to her bedroom where she sat me down at her vanity.

She spent the next hour blow drying and styling my hair. After that, she painted my fingernails and toenails with a hot pink nail polish. She told me to relax and let the polish dry while she jumped in the shower. When she came out she had some lotion for both of us. She told me to take off my towel and squeezed some into my hands. Then she took off her towel, put some lotion in her hands and said, “Watch me and do the same.” She rubbed it on her arms, legs, stomach, and ass cheeks. I did the same.

Then she pointed to one of two neat sets of clothes on her bed. “That one is yours.” I started by pulling on a very sexy red lace panty with a white heart on the front. Next, I put on the matching red bra with some padding in the cups. Sis commented how proficient I was at hooking it in the back by myself. I watched her as she pulled the straps of her bra up her arms and over her shoulders. Then she reached behind her back and hooked it. Finally, she pulled each of her breasts into the cups and then adjusted the bra in place.

Next, she picked up the silicone breast forms and tucked each one into my bra cups. They had something sticky on them where they contacted my skin and after she pushed them like she was feeling me up, they felt like they were attached to me. I could actually feel her fingers rub across them.

Sis picked up a pair of black thigh-high stockings and pulled them up her legs while explaining to me the care required to prevent ripping them. She instructed me to do the same, which I did. I couldn’t believe the feeling of the stockings on my legs. It was hard to describe and it was making me hard.

Sis also noticed and said I was going to have to do something with that. She took my hand and led me into the bathroom next to the sink. Then she pulled down my panties and started jerking me off with her hand. It only took about three minutes and I yelled, “I’m going to cum.” She placed her other hand in front of my cock to deflect my cum into the sink.

“What a mess,” she said. Then she smiled and rubbed her cum-filled hand over my mouth while grumbling, “How do you like that?” This took me by surprise and I couldn’t help but taste it on my lips. She was washing her hands and the sink while I was still in shock. I pushed her away and put my mouth under the still-running water. Sis put both her arms around me saying, “I’m sorry, that was wrong, please, forgive me.”

I smiled at her, reached down to my still-dribbling dick with one of my fingers, and then put the finger in her mouth. “You’re forgiven,” I said. She took a washcloth, wet it, and wiped my dick clean. She threw the washcloth in the hamper and gave me a little kiss on my cheek.

We both went back into the bedroom and put our dresses on. Just as before, Sis buttoned my bottom buttons and left the top three open. Then she sat me down at her vanity and started the makeup. It took at least twenty minutes for makeup, eyeliner, lipstick and a few other things. Then she turned me around so I could look in the mirror. I couldn’t believe it was me. Sis truly transformed me into a gorgeous woman. Jerking me off was a good idea. I was relaxed and calm. I really felt comfortable and feminine.

Sis finished her makeup before showing me how to apply lipstick. She said I would probably have to re-do my lipstick several times through the night. She put perfume on both of our necks. Then she grabbed a purse she had picked out for me. She showed me where the lipstick, makeup brush, hairbrush, and breath mints were in the purse. Then she opened the other side where there were several packs of condoms. She put her finger on my lips and said, “You never know when you might need them.” I didn’t reply. Sis went to her closet and threw me a pair of black flat shoes. They were like wearing loafers, only more open.

“I think we’re ready,” she declared. “Are you okay?” 

I just shook my head yes with a little smile.

Sis grabbed two of her shorter coats and gave me one. I put it on, grabbed my purse, and we went out the front door. As soon as we started walking I could feel the cool air blowing up my dress. This was another new and wonderful feeling for me tonight.

Sis said, “Watch closely how I and the other women walk. We really didn’t get any practice time. Also, whisper when you talk to hide your real voice. We’ll practice talking in the car on the way.” Sis opened my door so she could show me how a lady gets into a car. She said the trick is to never open your legs when sitting or getting up. This turned out to be great advice. I leaned back as I bent my knees until my butt was in the seat, then I rotated into the seat still keeping my knees together. I thought I looked pretty good on my first time.

We had to drive almost forty minutes to the party. This was actually good since it took us a comfortable distance from our neighborhood and friends. Sis and I talked the entire way to practice on my voice. She also kept giving me advice on how a woman should act as she thought about things during our conversation.

We parked in the street across from the house. There were quite a few cars and people going in and out of the front door. As soon as I opened the door and stood feeling the cool air up my dress, the excitement overtook any nervousness I might have had. I was glad Sis picked out flat shoes so I didn’t have the added problem of walking in heels. She took my hand as we walked across the street toward the house.

The front door was open when we walked up the steps so we just walked in. There were at least thirty people in the living room and adjoining great room. Music was playing, people were talking loud, most were drinking; we blended in with the crowd. Someone across the room yelled, “Hey, Amanda.” It was the hostess and Amanda’s friend from school.

As she came up to us Sis said, “Michelle, this is my friend Joann. Jo, this is Michelle.”

“Glad to meet you, Joann,” Michelle replied. “Make yourselves comfortable. There’s food and drinks in the kitchen.”

We went to the kitchen and each took a wine cooler. Then we walked through a sliding glass door into an enclosed patio where we found an empty couch. Sis sat on the one end and I sat next to her with my legs crossed. Sis said, “Here we are on a couch, again.” We both laughed.

A few minutes later two guys walked over to us. One sat down next to me while the other stood in front of us and asked, “How are you two girls doing tonight?”

Sis said, “We’re good, this is my friend Joann and my name is Amanda.”

The one standing said, “I’m Jimmy and that’s Bob,” as he pointed to the guy next to me.

Bob reached over and took my hand in a light handshake declaring, “It’s nice to meet you, Jo.”

I whispered, “It’s nice to meet you, Bob."

Sis jumped in to help me by starting some light conversation where I could participate with a simple “Yes,” “I remember,” “No way," and similar remarks to minimize my talking.

Bob asked me if he could get me another drink to which I replied, “Yes, thank you.” He placed his left hand on my knee to help himself get up. When he returned with our drinks, he handed me mine before sitting as close as possible.  This time, resting his hand on my leg above my knee. In the meantime, Jimmy found a portable chair and placed it facing Amanda and me.

After a few more minutes of conversation, Jimmy asked who we were dressed as. Amanda told him, “Two Broke Girls.”

He replied it was not much of a costume. I couldn’t believe Amanda shot back, “Yes, it is. Neither one of us are girls.”

Jimmy almost fell off his chair and sat there for a minute without a word.

Bob whispered in my ear, “I don’t care, I think you’re cute,” as he moved his hand a little further up my leg. Jimmy stood up shaking his head and walked away.

Sis then said, “I’ll leave you two alone for a little. I want to go talk to Michelle,” as she winked at me, stood up, and walked into the kitchen.

Bob lifted his left arm up and put it around my shoulder. “You and Amanda are amazing. You’re both so beautiful.” He continued talking a little about himself as he stroked my hair with his hand. I was getting goosebumps. Then he asked me if wanted to go outside and smoke a joint.

Suddenly, memories of a past experience came back to me. Then I thought, This time is different, so I said, “Sure.”

There were a pool and a cabana in the backyard. We sat on a bench as Bob lit a joint. As we smoked it, Bob began to rub my leg working up my right side along my breast. Then he leaned in and kissed me lightly on the lips. I stood up. He finished the joint, stood up, and then put both his arms around my waist. He put his lips against mine, and in what must have been a reflex, I put my arms around his neck. He pushed his tongue into my mouth as his hands slowly dropped to my ass. Again, I could feel the cool air up my dress. I could feel the stockings caressing my legs, my breasts against his body, his hands rubbing my ass. I was suddenly in heaven. As we continued to kiss I could feel his dick hardening as it rubbed against the front of me. My heart was pounding. I thought I was going to explode.

I pulled away and took one of his hands in mine. I pulled him around the back of the cabana out of sight where some lawn furniture was wrapped for the winter. I unbuckled his belt, unzipped his fly and reached into his shorts where I found his beautiful cock. I’m not sure who was more surprised, him or me. His cock was warm and wet from his precum.

He put his hands on my shoulders and started to push me down a little. Although I understood what he wanted, I wasn’t sure if I wanted to go there. But I did start this encounter. So I bent down and licked the end of his cock. This was the first time I ever touched another cock, let alone with my tongue. It wasn’t bad. I licked it a few more times and I knew I was going to have to go further. I opened my mouth and moved my head forward feeling the almost hot shaft sliding through my lips and onto my tongue. I could feel the vein on the bottom side of his dick on my tongue. I could feel the slobber in my mouth coating his dick. It was sliding in and out easier every time I bobbed my head.

I pulled back, stood up, and fumbled through my pocketbook for the condoms. I found a pack, opened it, removed the condom and rolled it onto his glistening dick. I’m sure there was no doubt in Bob’s mind what was next.

I bent over the covered lawn furniture, looked back at Bob, and said, “Go easy at first.”

He pushed my dress up over my ass, pulled my panties down to my thigh-highs, and put the end of his dick against my waiting hole. Then, as I asked, he pushed the head of his dick very slowly. It was softer, yet bigger than Sis’s dildo. There was no pain as it pushed open my sphincter. The condom was lubricated and studded. As the head of his dick passed through the entry I could feel it tighten on the slightly smaller shaft. I could actually feel the studs of the condom slipping along my sphincter as Bob continued to feed his cock into my ass. My ass began to feel warm and filled while my legs were cool from the autumn night air. His hands were firmly on my hips to help pull him completely into me.

Finally, his legs were tight against my cheeks. I pushed myself back into him to get his dick as far into my ass as possible. Then I moved forward a little signaling him that it was time to fuck. He didn’t need any instruction. He pulled back a little then pushed his dick in as far as he could. I could feel that familiar dizziness as my ass responded to the friction of his dick. As he started moving in and out I found myself pushing back on his forward thrusts. My ass was getting hotter.

As he picked up the pace I could feel his hands grip my hips tighter and I could hear him almost gasping for air. I pushed back as far as I could then I started to stand. His hands moved up my hips to my waist, then to my breasts. He started to squeeze my breasts while lifting my feet off the ground as he pushed his dick into my ass standing straight up.

His mouth was on the back of my neck and I could hear his labored breathing. I put my hands on top of his on my breasts as he bounced me off the ground with his upward thrusts. Suddenly, he started to bite the back of my neck; I could feel him tense up. He was struggling to restrain his sounds as he came in my ass. He squeezed me in a bear hug and stood straight up lifting me completely off my feet as his orgasm reached its peak.

As he stood motionless in his tight grip on me I instinctively reached my hand down to cover my dick just in time to keep from shooting come all over my dress. My hand was full of come and I didn’t want to wipe it on my dress. I held my hand up to my mouth and licked it off.

After a few minutes, Bob leaned forward until my feet were back on the ground. I leaned forward over the lawn furniture. I could feel his dick soften in my tight ass as he moved his hands back down to my hips.  After a few more minutes, he slowly pushed back pulling his dick out of my ass. I could feel the cool air on my hot ass and the emptiness. I reached down and pulled up my panties. Then I pulled my dress down. I was still feeling a wonderful tingle in my ass.

I looked at Bob. He leaned forward and kissed me full on the lips before saying, “That was the best sex I’ve ever had in my entire life. I hope we can do this again, Joann.”

I told him to give me his phone number before we left.

I grabbed my pocketbook and walked toward the house when I thought about how I might look. I walked back to the cabana and tried the door toward the pool. It was unlocked. I fumbled for a light switch and was surprised to find it was a bathroom. Lucky me, I was able to redo my lipstick like Sis showed me, straighten out my dress, and pull my thigh-highs back up all the way. I sat on the toilet to take a pee before heading back into the house.

Once in the house, I milled about looking for Sis. When I couldn’t find her right away I got another wine cooler and sat on the couch. Bob came over, sat next to me with a big smile, then handed me a piece of paper with his phone number on it. “I hope you call me,” he said.

I replied, “I will, you were great.” We sat for a few minutes when Sis came over and asked if I was ready to go.

I responded, “Whenever you’re ready.”

So she said, “Let’s go, then." With that, I leaned over and gave Bob a kiss on the cheek. I could see the surprised look on Sis’s face as I stood up.

“Should I ask?” she said as we walked toward the front door.

I replied, “Maybe later.” I was feeling too good to spoil it with too much thought. I just wanted to finish the night as a woman.