Like most teens, I faced a number of depressing challenges. These challenges, unfortunately, dominated me as an adult. As the youngest with three older sisters, I grew up far more in touch with my feminine side than even I would have liked; this resulted in being much more of a private person. The confusion put a huge strain on almost every relationship I had; either because I smothered those closest to me or because I unloaded my problems onto them – or both; and they never really signed up to be my therapist.
I was a very attractive man at least that is what I was always told. Not the buff weightlifting jock, but more of a skinny nerd. What I lacked in athleticism, I more than gained in sensitivity. Making new friends, especially girlfriends was never a problem, keeping them was. For the girls, my sensitivity and ability to lean on my past experiences with my sisters was an advantage, but for the guys, I was often misunderstood – my sexuality was often in question at least when I was not in the room. The labels I discovered contributed to my exploration.
I became so depressed and lonely, I began to experiment and often considered becoming a woman. It started with dressing in en femme and because of my thin physique; I was often very passable as a woman – at least from the neck down. As time went on, I continued to perfect my look and even ventured out a few times late at night to see what it was like to be out as a woman.
After college, I moved away to begin a new career and hopefully build a new life with new people. Far enough away to go relatively unknown, but close enough to my family that I could go home. Living on a budget was common for rookies just starting out, but I valued my space so I struggled to maintain my two-bedroom apartment. While the bachelor pad was intact, the guest room was a retreat of sorts. On the surface, you would think that Billy had a roommate, but the guest room was not for sleeping; the closet, filled with women’s clothes and shoes; a make-up table and floor-length mirror and a chaise lounge that allowed my to pose in different positions instead of just standing or walking in the room.
It was rare that anyone ever came by the apartment and those that did never ventured into the guest room, so I was very comfortable when he was home. This was my life, and I was very happy. Then it happened.
After a hard week at work, I was about to enjoy a four day holiday weekend. Usually, I would head home and visit with my family, but the last few weeks had been very stressful. Work and financial struggles took their toll, so I decided to stay home and calm the nerves. On the way home, I stopped and pick up a few groceries so I wouldn’t have to leave the apartment.
When I arrived, I walked in to find a maintenance man in the apartment and the guest room door was wide open.
“Hello?” I said.
“Hi, I am almost finished.” the maintenance man replied.
“Finished with what?” I asked.
“There’s a leak in the apartment upstairs and we needed to get to it from your ceiling.” The maintenance man explained.
I immediately began looking around the area the repairman was working and became concerned about my things being discovered or worse ruined.
“Don’t worry, we moved the items to the couch behind you,” the repairman said.
“Was there any water damage?” I asked.
“Not here.” the repairman explained.
Just then another plumber walked in to replace the faulty pipe. The first repairman walked back towards the front door as I followed him. Before he walked out, the repairman turned and introduced himself.
“I’m Steve by the way,” he said.
“Billy,” I replied as I extended his hand.
“You have a great place,” Steve said.
“Thanks”, I replied.
“Do you have big plans for the long weekend?” Steve asked.
“Not really, just sticking around here,” I replied.
“Well, if you are not doing anything and want to get away for a little while, I’m having a little party tomorrow night.” Steve explained, “You’re welcome to stop by.”
“Thanks, but I don’t know. I may just stay here and catch up on a few things.” I said.
“Come on it will be fun.” Steve said as he wrote the address on a piece of paper, “You can dress up if you like.”
I just looked at Steve in amazement. How did he figure it out so fast? I didn’t say anything, just stood there as Steve walked out the front door. I immediately picked up the piece of paper and simply threw it in the trash can.
I tried to avoid talking to Steve while he and the plumber continued to work on the repairs. When they were done, I escorted them to the door.
“Hope to see you tomorrow night,” Steve said.
“I don’t know, I’ll think about it,” I replied.
As it got later in the evening, I dressed for the occasion in a simple nightgown after taking a long hot bath. I spent the rest of the evening in the bedroom curled up in bed, reading a book before falling asleep.
The next morning, I got up and threw on a robe and went to the kitchen to make breakfast. Sitting at the table with a cup of coffee, I continued to think about how Steve was so intuitive and found out my little secret. I walked into the room and looked around. Putting the clothes back in the closet that was moved to make room for the repairs. I sat in the chair in front of the make-up table and looked around for clues that could have given Steve the truth.
After spending almost an hour in the room, I walked through the rest of the apartment. Investigating each room, I couldn’t find anything – outside of the room itself – that would give away my secret life. So how did he figure it out? I needed to find out and there was only one way to do that.
I made the decision to attend Steve’s party. I figured I would be there long enough to ask the question and depart without being noticed. It also gave me the opportunity to go out en femme – since Steve was the only one who knew and I didn’t have many friends – I figured going out in disguise would be okay and I wouldn’t be recognized.
So I took the rest of the afternoon to get ready. After a long hot bath where I shaved his legs, arms, underarms, and groomed my private areas, I stepped into the guest room where I began my transformation from “Billy” to “Billie”.
I started with a pair of black panties, which squeezed my tight butt and hid my modest man-parts nicely. I then put on a padded black bra. Looking in the mirror, you could see the transformation taking shape.
I then pulled on a pair of black tights followed by a plaid skirt and a white top that barely hid the black bra underneath. I added a wide leather belt and ankle boots to complete the ensemble before moving above the neck.
I was never one for a lot of makeup and usually kept it very natural and subtle. Simple foundation, a pink blush, and light smokey eyes, followed by a simple rose-colored lipstick. I added hair extensions to build a long straight hairstyle with a little bit of volume. With a scarf to cover my neck, I was now almost ready to go.
I needed to rehearse the outing… walking around making sure my posture and walk was lady-like; my hand gestures and mannerisms also had to match my disguise sitting like a lady and making sure I could pass for any other woman. I also practiced my voice a little to sound as believable as I looked.
After I was satisfied, I grabbed a small handbag from the closet and my keys and once the sun went down, I covertly made my way to the car and headed to the address Steve gave me. I took my time, by making a few stops on the way – at the gas station, drug store, and coffee shop – getting down and going in to practice a little more.
I was very observant – almost paranoid – about those around me, but the only thing I noticed was a few younger men checking me out thinking about what was underneath the skirt. Other than that, I wasn’t noticed at all. I arrived about a half-hour later and sat in the car, still undecided. Should I go in or not?
I took a deep breath and hopped out of the car. As I walked towards the loud music coming from the back of the house, I was continuing to rehearse what “Billie” would be saying to Steve. As I followed the handwritten signs and walked to the back yard, I became more and more nervous. I then heard a familiar voice.
“Hey!!!” Steve yelled as he saw me, “I am so glad you made it.”
“Well I can’t stay long,” I replied.
“Don’t be silly,” Steve said, “Stick around. Have a good time.”
“I really just wanted to talk to you,” I explained, “Besides, I really don’t know anyone.”
“Sure, I understand, Hey Rick, come over here,” Steve said as he called one of his friends over.
“What’s up, Steve?” Rick asked.
“Rick, this is…” Steve tried to introduce me but didn’t know my name.
“Billie,” I said.
“Right, Billie.” Steve said, “Billie, this is Rick.”
We shook hands as Steve walked away. I wanted to follow Steve but didn’t want to be rude to Rick.
“So, how do you know Steve?” Rick asked.
“He did some work at my apartment,” I replied.
“Oh, Steve and I grew up together,” Rick added.
We continued to talk, but Rick could tell I was distracted as I continued to look for Steve.
“Are you okay?” Rick asked.
“Sure why?” I asked.
“You look a little uncomfortable,” Rick said.
“I just feel a little out of place,” I said, “I really don’t know anyone. I just wanted to talk to Steve for a couple of minutes anyway. Maybe I’ll just go.”
“No, don’t go,” Rick said, “Have a drink and stay awhile. Steve’s not going anywhere.”
I had a couple of drinks and started to loosen up a bit. I noticed I was moving more to the music and I was not the only one who noticed.
“See there ya go,” Rick said, “Have a little fun.”
As the evening moved into the early morning, I started to really open up more. Rick and I danced with each other and talked most of the evening. It was the first time I had been held by a man and we seemed to get closer every minute.
The party started to die down a little bit and Rick and I moved to a quiet spot in the backyard. I was getting to know Rick really well and before I could stop him, Rick leaned over and kissed me. I pulled back quickly and we looked at each other and I became hypnotized by his stare and I leaned back in and the two of us began kissing passionately.
Rick’s hands caressed my shoulders and back while I wrapped my hands around his waist and pulled him closer to me. I was no longer concerned about talking to Steve. I had discovered something I had been looking for all my life. Rick moved his hands down to my thighs, but with my legs crossed and pressed together, I protected my secret.
I wasn’t quite sure why, but I had never been happier; but the happiness would not last and would take a turn, as I heard some laughter in the distance. The laughter continued to get louder and Rick and I broke our connection – only to see Steve and a couple of his friends staring at them.
“What’s so damn funny?” Rick asked.
“Dude, you’re sick, Steve said.
“What are you talking about?” Rick asked again.
“Dude… that’s a guy.” Steve announced.
Rick then looked at me and popped up out of his seat, Dropping me to my knees. I began to cry and ran to my car as they laughed at me. My last memory of Rick was the look of shock on his face and I wasn’t about to stick around for further humiliation. I struggled to unlock the car door and sped off and headed home.
When I got home, I was still fighting the tears and sat on the floor against the door. About an hour later, there was a knock at the door. I got to my feet and looked through the peephole to find Rick standing outside.
“Go away,” I said.
“Billie, it’s Rick,” Rick said, “Please open the door.”
“Go away,” I said.
“Come on, Billie, I just want to talk,” Rick replied.
I cleared away the tears rubbing the makeup across my face and opened the door.
“What do you want?” I asked.
“Are you okay?” Rick asked.
“Do I look okay?” I asked.
“I am really sorry about all this.” Rick said, “Steve can be a dick sometimes.”
“Yeah,” I replied as she walked to the table to get a tissue.
Rick walked in and closed the door and walked over to me. He stood behind me and tried to console me further.
“Are you going to be okay?” Rick asked.
“I’ll be fine,” I said, “You should go.”
“Why didn’t you tell me?” Rick asked.
“I don’t know, I had never done this before,” I said.
“You never dressed before?” Rick asked.
“No. Never gone out to socialize before,” I said.
“Why didn’t you stop me when I kissed you?” Rick asked.
“I don’t know that either,” I explained, “I had never done that either.”
Rick sat down next to me on the couch and put his arm around me.
“What are you doing?” I asked.
“Shhh,” Rick said as he leaned in and kissed me.
“What are you doing?” I asked again as she hopped up from her seat.
“It’s okay,” Rick said, “I really like you.”
“You don’t even know me,” I said.
“Yeah, well what I know, I really like,” Rick replied.
“What about Steve?” I asked.
“What about him?” Rick asked.
“He could make things hard for both of us,” I said.
“Don’t worry about that coward,” Rick explained, “He won’t say a word. I have enough on him to keep him quiet.”
I felt a sense of calm as I listened to Rick. I stood motionless as Rick stood up and walked back over to me and put his arms around me. He kissed the top of my head and walked towards the door.
“If you ever want to talk… or hang out sometime, give me a call,” Rick said as he put his business card on the table.
“Wait. Don’t go,” I said.
Rick turned around as I walked back over to him and kissed him passionately on the lips. Rick hoisted me up in his arms and carried me back to the couch where the two of us continued making out. I began to unbutton Rick’s shirt and worked my hands down to his pants. I placed my hand on his crotch, which was pressing against his jeans. Rick pulled me up to his lap where I was sitting on him. We continued to kiss as I continued trying to get into Rick’s pants, but Rick continued to move my hands away.
“What’s wrong?” I asked.
“Are you sure you want to do this?” Rick asked.
“No, but did you really expect to meet me tonight knowing what you know now?” I asked.
“What’s your point?” he asked.
“If I were a woman, would you stop me?” I asked.
He allowed me to continue. I moved next to him, unbuttoned his pants and reached in to find a sizable piece of meat. I continued to pull gently at his cock. As we continued to make out, I continued to stroke his cock which was growing and getting harder by the second.
I then slid down and squatted in front of Rick. I pulled his pants down further exposing his cock and with both hands continued to stroke him. His head fell back against the couch as I continued maintaining my grip. As both of us closed our eyes, things got very interesting.
I leaned forward and began licking Rick’s cock; slowly, but enough to get the shaft wet and subsequently to get Rick to moan.
“That feels good,” Rick said.
I continued to lick his cock and cradle his balls as Rick continued to groan uncontrollably. He then put his hand on the back of my head and with the next lick of his shaft he pulled me forward and I opened my mouth wider to take in every inch. I took it in as far as I could and closed my mouth, wrapping my lips around his shaft firmly and gently began to suck.
“Oh you are really good at this,” Rick said softly, “That feels so good.”
I began to move my head up and down on the shaft, drooling on it and sucking it firm enough to keep him moaning. Rick tried to reach for his pants to take them off but needed my help. Without hesitating and without breaking her mouth grip on Rick, I was able to take off his shoes and slid his pants off. I then ran my fingers up his legs back up to his groin and continued to orally pleasure him.
Rick arched his back and pulled my head back. I remained in front of him waiting for him to explode with my hands on his knees.
“I would really like to be inside you,” Rick said.
I looked at him with a look of fear and curiosity. I wasn’t sure what to say to him. Outside of using toys, I had never done that before.
“I’ve never done that before,” I said.
“You don’t have to,” Rick replied.
“I’m just not sure I can,” I said.
Rick leaned forward and said, “It’s okay.”
He leaned back and began stroking himself slowly. I felt so guilty watching him take matters into his own hands and not giving Rick what he really wanted; so I tried to make it up to him. I moved his hands and went back to sucking his cock until he came all over my face. I licked all of his juices from his cock then gently laid my head against him.
Later, after Rick cleaned up, I asked him to stay since it was really late. I remained dressed but went to the bathroom to clean my face and fix my makeup, so I was still passable. I returned and laid in bed with him as we both fell asleep.
The next morning, I got up and walked down the hall to the guest room, where I changed clothes and freshened up. Rick woke up and walked down the hall to find me sitting in front of the mirror.
He instantly became aroused as he saw me wearing a red lace lingerie set complete with a thong, garter and fishnet nylons. He startled me as he walked in and I popped up, scrambling to find my robe.
“Is all this for me?” Rick asked.
“Do you like what you see?” I asked as I dropped the robe.
“Oh yeah, you look beautiful,” Rick said.
I walked back over to Rick who stood there in his boxers. I reached up and kissed him and immediately squatted back down and pulled down his boxers uncovering his package. I began getting his cock nice and wet as Rick stood there with his head back, enjoying every minute of my service. I then stood up and pulled his head closer to me.
“Do you want me?” I whispered.
Rick looked into my eyes and could tell I was serious and very willing. I then pulled away from him and leaned over the chaise lounge, bending over showing Rick my ass. I began rubbing my cheeks slowly with an occasional smack.
“Are you sure?” Rick asked.
“I am now,” I said.
Rick slowly moved over to my backside – gently grabbing my ass.
“Come on baby,” I said.
“Your ass is so awesome,” Rick said.
“Give it to me, Rick,” I said, “I need you.”
Rick moved in closer and the next sensation I felt was indescribable.
“OOOOHHHH, what are you doing?” I asked.
“Do you like that?” Rick asked as he began eating my ass.
“Oh god, that feels good baby,” I replied.
He continued using his tongue, tickling my pussy. I pulled my penis and testicles away, keeping the image of his fucking a woman intact. Rick never reacted but knew exactly what he was doing. He then got up and rubbed his cock over my now wet virgin hole.
“Are you ready?” Rick asked.
“Oh yes, baby,” I said, “Give it to me.”
He continued to wet his cock and my hole, then began to press it against my opening. I could feel the pressure of his cock against my pussy as I began to moan, begging for Rick to penetrate me. He then pushed his cock into me very slowly.
“AAAAAAOOWWWWWW,” I screamed.
“Are you okay?” Rick asked.
“It hurts,” I said.
“Do you want me to stop?” Rick asked.
“No… No, I want you inside me,” I replied.
He continued to push into me as I continued to scream. My screams became moans of pleasure as he pushed his cock all the way in. He left it there and slowly moved it back and forth as I continued to enjoy the sensation.
“Oh… god… you’re so big,” I said, “I love you inside me.”
“You feel so good,” Rick said
“Come on baby,” I said.
Rick pulled out slowly and I let out a huge groan of pleasure.
“More… Please… More…,” Billie begged.
Rick proceeded to push in and out of me as I came all over my legs.
“Keep going honey, I want you inside me,” I said.
He moved in and penetrated me faster and faster until he was ready to cum again. He pulled out and came all over my back and ass, rubbing his cock against my ass, spreading his cum all over my cheeks. I reached back to touch the gift he left for me, then turned back looking at Rick licking her fingers.
After we were done, Rick cleaned up in the shower while I stood and watched.
“What do we do now?” I asked.
“What do you mean?” Rick asked.
“I don’t know, I mean, I would like to see you again,” I said.
“Me too,” Rick replied.
“What about Steve and your friends?” I asked.
“You can’t get passed that can you,” Rick replied.
“It’s kinda hard to get passed what happened at the party last night,” I said.
“No, you’re right,” Rick said as he dried off, “but you can’t let that bother you. You are more than I bargained for. Let me worry about Steve. All you have to do is stay beautiful.”
“But a beautiful what?” I asked.
“Would it bother you if I said I would want to see you this way?” Rick asked.
“It might… as you said, I am more than just this,” I replied.
“Well hopefully, I can learn to love both sides of you,” Rick said as he walked over to her and kissed her.
“I look forward to that day too,” I replied, “I really do.”
Rick finished getting dressed and left the apartment. I scurried to the guest room and got undressed and got into the bathtub. All I could think of the rest of the weekend was the incredible sex I had and how I found the one thing in my life I had been missing – a real man.