As my time in high school was reaching an end, I found myself with more time on my hands. I was no longer searching for colleges as I was recently accepted to my first choice. I was no longer working at my part time job since I was now trying to focus on finishing school. I also noticed that I was home alone more and more often. Something I loved since living in a house with three women can be difficult for the only male. Mom was dating a new man in her life and my older sister was working nights so I had a lot of time to be me.
We were coming up on a long weekend and mom was spending it with her new boyfriend and his family. She planned to take my younger sister with her, but me and my older sister was not planning to go with her. “Big Sis” was picking up another shift at work so I would have the entire house to myself. As the weekend approached, I was getting more and more excited. I wasn’t planning on leaving the house and was looking forward to dressing up and playing house.
Mom left with our baby sister after work on Friday afternoon and My older sister left for work early Saturday morning. I also got an early start to the day. I jumped in the shower and shaved my legs as I was doing more often, I then slid on a nice lacey thong and a pair of tan pantyhose, threw on my long pajamas and slippers and headed back to my bedroom until Sis left the house for work. While I was paranoid that they might know I was dressing up in women’s clothes and was riding both sides of the sexual fence, I didn’t want to be obvious and assume.
After she left, I jumped out of bed and into a new white minidress I had in my closet that showed off my long legs and barely covered by butt. I then slipped on a pair of blue flats and went to the kitchen to make breakfast. I sat at the table – remembering to sit like a lady and cover up all the important parts. After breakfast, I got started on the day. A throwback to the 1950’s where maintaining the home was “woman’s work”. I started by taking care of the laundry, coming back to the kitchen to take care of the dishes and then finished up the morning with some vacuuming. I stopped to make a sandwich for lunch and sat on the floor in front of the TV.
Then it happened. I fell asleep right there on the floor. While the excitement of dressing en femme was exhilarating, it was also exhausting. I wasn’t too worried about it since Mom was out of town and my sister wouldn’t be home from work until late that evening. What I didn’t plan for was Sis coming home early.
I woke up a few hours later and as I adjusted to my surroundings, I turned to find my sister sitting on the couch in front of me.
“Well good morning, Honey.” she said, “Did you enjoy your nap?”
Realizing that I was completely exposed, I got up and ran to my bedroom and locked my door. I sat down on the floor and was filled with so much emotion that I started to cry. I could hear my sister walk down the hall towards my room, and didn’t know how I was going to explain any of this.
She knocked at the door and said, “Are you okay?”
When I didn’t respond, she said, “Please open the door. Let’s talk about this.”
I slowly got to my feet and while I was still dressed I took a deep breath and unlocked the door. Leaving it closed I walked and sat on the bed. My sister, Julie, opened the door slowly and saw me sitting there with my head down and chin tucked into my chest. She sat next to me on the bed and took me by the hand.
“I want you to know, I have known about this for a while.” she said.
I never moved but hung on every word.
“It’s okay.” she said, “Mom tells me all the time that she doesn’t care what we did in life as long as we were happy… and if this makes you happy, then it’s okay.”
I looked up at her as she slowly wiped my face. She then straightened the skirt from my dress to cover my legs slightly and then started asking me the toughest question I would have to answer.
“Is this what you want?” she asked.
“I don’t know?” I whispered.
“Do you want to be a woman?” she asked.
“I’m not sure.” I replied.
“Are you being careful?” she asked.
“What do you mean?” I replied.
“Have you been with anyone?” she asked.
“No… Wait what do you mean?” I replied.
“Are you having sex?” she asked.
“No, I am not with anyone.” I said emphatically.
“Okay, good.” she said, “Does this turn you on?”
“Julie!?!” I said.
“I’m sorry, I just want to try and help.” she responded.
I paused for a minute and then shook my head and replied, “A little.”
Of course I was lying, I was really turned on by it.
“Okay, Is there anything I can do to help?” she asked.
As soon as she said that there was only one response I could give her.
“Please don’t tell Mom.” I begged.
“Don’t worry about Mom, She already knows too, but she is not going to admit it unless you sit with her and talk to her about it.” she explained.
I now felt worse.
“I don’t know what to do now.” I said.
“What do you mean?” she asked.
“I feel embarrassed.” I said.
“I know and that’s just because I came home early.” she replied, “But I want to help and your secret is safe with me… even from Mom. All I want to do is help.”
When she said that I was a little more relaxed and trusted her completely, so I opened up and told her everything. How it started and how far I had progressed. I told her how I had gone out dressed before and even done a little shopping. The sex part was the hardest thing to talk about. While I had been alone, I was enjoying sex but just not the traditional straight man sex that most might be accustomed to.
“Do you think you are gay?” she asked.
“I don’t know, maybe.” I explained, “I mean, I still love the sight of a pretty girl and get excited when a girl gives me attention, but I have been thinking more about being with a man.”
“I can understand you are confused, but until you see what that is like I don’t think you will be able to get passed it.” she said, “but you have to be careful.”
“I know, I just don’t know how to do that without being exposed.” I replied.
“Well maybe when the time is right it will happen, you can’t force it to happen.” she said.
Of course she was right. What happened next was completely unexpected. Julie got up and took me to the bathroom and got me cleaned up. She then helped me perfect my makeup which I thought I was getting really good at, but she showed me how to best use colors and then she took me to her closet and started handing me outfits she no longer wanted. When she found something she thought would look good on me, she had nme try it on. That evening her boyfriend showed up with friend of his. I was still dressed and not really ready to interact with anyone else – much less her boyfriend and a complete stranger.
“Don’t worry, it will be okay.” she said, “Jimmy knows and I trust him.”
“That’s not the issue, Julie and you know it.” I said.
“Look you have already been out in public. This is no different and it is safer anyway.” she said, “Don’t worry I am not going to leave you alone – unless you want me to.”
I hesitated but agreed to the “double date”. Julie helped me pick out a nice miniskirt outfit that I wore with black tights and a white top covering the padded black bra.
“I’m not sure I can do this.” I said.
“Look take your time, when you are ready, come out and join us.” she said.
I sat in the room for what seemed to be hours, but I looked at the clock and it was really only 15 minutes before there was a knock at the open door.
“Hope I’m not bothering you.” Jimmy’s friend said, “I was just wondering if you were hungry… we ordered pizza.”
I was quickly startled and scrambled for a blanks on my bed.
“I’m sorry, if I scared you.” he said, “If you’d like I’ll go back to the living room.”
“No, it’s okay. I need to do this.” I said.
“Do what?” he said as he came and sat next to me.
“Nothing,” I said, “I’m Brenda.”
“I know, Julie told me, I’m Drew.” he said.
We shook hands and talked a bit. He knew a little about me, and I learned quite a bit about him. He was Jimmy’s AA sponsor and helped him through some tough times. As he talked, I noticed that his mannerisms were manly but a little more on the feminine side. It wasn’t long until I confirmed he was in fact, gay. When I asked him directly and he said yes, I became a little more angry at Julie for trying to fix me up, but I got over that quickly since I was enjoying the conversation.
Julie and Jimmy came down the hall and saw us sitting on the bed.
“We were thinking of going to the drive in to see a movie, do you want to come with us?” Julie asked.
Drew and I looked at each other and without saying a word, we mutually decided not to go with them.
“No I think we will just stay here.” I said.
“Are you sure?” Julie asked.
I looked at Drew one more time and replied, “Yeah I think so.”
Before they left Julie took me into her room and again wanted to make sure I was okay with staying alone with Drew. I told her that I wasn’t really happy with the fix up but I told her I would be okay.
So Jimmy and Julie left and Drew and I went out to the living room, where we continued to talk. As we did, I found myself opening up more to him. Explaining to him what I was going through and how frustrating it was. Surprisingly, he understood and said, he went through a similar situation and it wasn’t he overdosed that he realized that the chances he was taking were riskier than coming to grips with the fact that he was gay.
“I tried to hide it too long and pretend I was straight.” he said, “That is when I started drinking. I thought the drunker I got the better chance I had of hooking up with someone.”
I thought that sounded stupid and it was, but he was so frustrated and lonely, he didn’t see any other way.
“How did you come out?” I asked.
“I didn’t, really.” he said, “I realized my private life was private. If I got close enough to someone I trusted I would be honest at that point and trust they would not try and expose me, but that is obviously a little harder for you.”
“Yeah a little.” I said.
“But you can still be private.” he said.
“What do you mean?” I asked.
“I am looking at you now and I can see the picture on the wall and I see two totally different people.” he explained, “That is the easy part. The hard part is when you meet someone you would like to be with and they are expecting to see a woman… not a man.”
“Yeah I guess you’re right.” I replied, “I guess it comes down to trust.”
He then took my hand and we continued to watch TV. As we did I rested my head on his shoulder. We sat there for only a couple of minutes before we looked at each other and kissed. IT was a first for me so I didn’t know what to expect, but it was so great that I stayed close hoping he would continue and he did. His hands ran down my back and onto my hips as I ran my hands down his face and chest.
I could feel him start to suck on my neck and the feeling was awesome. I held his head in place with one hand as I continued to run my other hand up and down his body while he began to caress my nylon-covered butt. He then stopped and looked at me. The look was a look I gave women I dated before, only in this case I was on the receiving end and unlike the girls I dated, this “girl” was willing.
I slid down to my knees kneeling between his legs in front of him. I began to rub my hands up his thighs and right over his crotch, which was bulging, trying to break through. I slowly unbuttoned his jeans and pulled them down far enough to expose his thick cock. I was very intimidated by it because it was so big, but I had gone this far, so I took a big deep breath and moved in. taking his meat in one hand and slowly licking the tip while I began to jerk him off.
As I wet his cock, his head fell back and he began to moan. I then went in for the tough part. I took another deep breath and slid his cock into my mouth and gently began to suck. Pulling back hard enough to get him to moan louder and louder.
“Oh damn that feels good.” he said.
I never came up for air, just continued to pleasure him, hoping he would explode.
“OH YEAH… YEAH… AAWWWHHHH FUCK YEAH.” he shouted.
He pulled me off him quickly and I was waiting for him to cum, but he just fell back and wanted to rest.
As I continued to stroke him, I asked, “Do you like that?”
“OH YEAH.” he said.
“You like it when I suck your cock?” I asked.
“Yeah I love it.” he said.
I started to move back down and he stopped me before I could get passed the tip.
“I want to fuck you right now.” he said.
I looked at him then looked at that giant piece of meat. I wasn’t sure I could take it, but I was really enjoying the fun so far so I took another chance.
“Be gentle with me okay” I begged.
“Okay baby. We will take it slow.” he said.
He then stood up over me still on my knees. I took his hand and he helped me up and we went to my bedroom. There I helped him take off his shirt and he helped me off with the dress leaving me in the black slip, bra and black tights. He started to bend me over and was attempting to pull down the very snug tights. When it wasn’t working with one hand, I gave him another suggestion.
“Tear through them like you are going to tear through me baby.” I said.
He grabbed a hold of the tights and ripped them, exposing my tight ass. I handed him the lube from my nightstand and he proceeded to penetrate me with his fingers first, to open me up a little bit.
“Oh god that feels good.” I said.
“Yeah baby, you like that?” he asked.
“Oh yeah baby, I love it when you push your fingers inside me.” I replied.
He continued that for a couple of minutes until I was ready.
“OH GOD…. FUCK! I WANT YOU INSIDE ME…” I said.
“You ready?” he asked.
“RIGHT NOW BABY… GIVE ME THAT HARD COCK.” I demanded.
He got up and lubed up and began pressing his cock inside me.
“AAAAEEYYYYYYOOOOWWWWWWW!” I screamed as he pushed his thick cock all the way inside me.
He stopped when it could go no further, allowing me time to get used to it, then he started moving back and forth slowly and the feeling was more than I ever hoped it would be.
“OH WOW… I LOVE YOUR TIGHT PUSSY.” he said.
“YEAH… YEAH… YOU LIKE BEING INSIDE ME BABY?” I asked.
“OH YEAH… FUCK YOU ARE SO TIGHT.” he said.
“POP MY CHERRY BABY… FUCK MY VIRGIN ASS.” I shouted.
He started to move faster and with each inch inside me I moaned and screamed louder and louder.
“OH… OH… I’M CUMMING…” he said.
“CUM ON MY ASS BABY…” I said.
He pushed in a couple more times then slide out and exploded all over my ass. I could feel the warm juices run down into my crack and along my back. I looked over my shoulder and saw how exhausted he was as he was clutching his cock. So I guided him to the bed and took a hold for myself. Squeezing out every drop and then I went back down on him to make sure he was nice and clean and I had the rest of his cum in my mouth. When we were done, we laid in bed together until I fell asleep. A couple hours later, I felt a kiss on the cheek and woke to see Drew getting dressed and preparing to leave.
“Is everything okay?” I asked
“Yeah, but I don’t want your sister to get upset with me.” he said.
I understood and threw on a bathrobe and walked him to the door. As he left I realized that Julie was already back home. I turned around to see her standing across the room.
“So did you get what you hoped for?” she asked.
I ran to her and wrapped my arms around her and yelled out “Oh god yes… it was better than I ever hoped.”
She hugged me back and we sat down and talked about the evening. I now had a new found trust in my sister and for her she now had a new sister she could mentor.