A day did not go by when I didn’t think about that night at Jimmy’s house. I would frequently wear the black bra and panties Missy gave me when I was alone at home or occasionally out with friends. My buddies and I were looking at girls in a completely different sense. I started looking at girls for what they were wearing and how they carried themselves. And my fellow sixteen-year-old friends, well they were looking at them as girls, as most sixteen-year-old boys would.

My debut as Jenni was not really discussed much among us. It came up occasionally, especially when we had a few beers, but it was generally off-topic given it was the eighties and times were different back then. My friends were deathly afraid to admit they “liked” Jenni, the transgender alter ego of their buddy Jeremy, and I never really brought it up either. However, I was thinking about it all the time.

I longed to be able to hang out with the guys as Jenni. My mind began to wander to very forbidden areas when I was with them as well. As much as I was looking at girls differently, I was also looking at the guys differently. I couldn’t help but think about how it would be for Jenni to be with them? How many of them really thought I was convincing enough as a girl that if they didn’t know me they wouldn’t have known my secret? It was a very awkward summer for me.

My home life was no help to me at all. My parents were very strict, religious, and conservative people. Don’t get me wrong, they were great parents, but to drop the news that I really enjoyed wearing girl’s clothes would be devastating. I would never dream of sharing my sexual curiosity with them. My bra and panty were very well hidden in my closet to the point where it was difficult even for me to get to them. To bring in some different outfits, makeup and shoes were nearly impossible. I was stuck.

Missy and I had good intentions to have another makeover session, but her summer schedule was crazy. Starting with cheerleading camp, her babysitting jobs, and of course, her boyfriend Pete, Missy was not nearly as accessible as I would have wanted her to be. We would occasionally bump into each other when I was over at their house. She would always ask if I was still interested in another makeover, if I was taking care of her gift, and of course always promise to make time, but it was the summer. I understood because I was just as busy. I just needed to be patient with my new found interest.

It was just before school was going to start when Missy presented me with a chance for Jenni to return. Her mom, dad, and Jimmy were going to go out of town over Labor Day weekend but she had two babysitting jobs that she couldn’t pass up and would be staying home. She said she had a job Friday night and Monday and plans with Pete on Sunday. However, she wanted to spend Saturday with me. Other than a BBQ on Sunday afternoon with some of my neighbors, I was open. I was in! The conversation turned to my preparation.

“So Jeremy, there are a few things you need to do before you come over. You’ve mentioned to me how much you think about being a dressed like a girl well now we need to take some action. You need to start by deciding what you want to wear.”

I shared with Missy that I would occasionally drive to the mall and make it a point to walk through the girl’s clothes section in every store. I would never have to guts though to stop and look or to go through the racks. Even if I did, I wouldn’t even know how to begin shopping. Missy pulled out a few of her teen magazines and gave me a few ideas but ultimately it would be up to me. She also reminded me that if I was going to go with my white gym shoes, I may want to girl them up a little with some pink laces. Her final direction was to make sure I completely shaved.

“You never know who may show up or where we may go, so don’t make your outfit too fancy. But let’s make sure your look like a cute young lady.”

I started to ask questions but was told to be quiet. Missy would be ready for hair and makeup. I needed to take care of everything else.

“You’re either all in or not, Jenni. You’ve wanted this all summer and now is your chance. You have just less than two weeks to make this happen and to get your head straight.”

“You’re right and I’ll be ready. Don’t worry.”

“Good girl. My parents and Jimmy are leaving Saturday morning. Call the house around 11 AM to make sure they are gone. I’m sure I’ll see you before then so just let me know if you have any questions.”

I ran home with the magazines that Missy had given me and went right upstairs to hide them in my room then ran back to Jimmy’s house and acted like I had forgotten my wallet. My mind wandered all night hanging out with the guys. They were trying to find a cute girl to hook up with while I was checking out what they were wearing. Later that night, I was lying in bed with a little pen flashlight paging through the teen girl magazines. I had settled on trying to find something with a little more color this time, figuring a poofy skirt, with a mesh top, a tank, and maybe some fishnet stockings. Then the realization hit that I was going to have to go shopping. My nervous anticipation just became nervousness.

I asked my mom if I could borrow her car during the week. I dropped her off at work and then headed to the mall. The only problem was I was an hour early. It was the longest hour of my life. I sat in the car listening to the radio reading the list I had written out for myself over and over again. I had gone back to the department store magazines to try and figure out what size I would be. Missy had coached me on a few things and given me a better idea on bra sizes just in case I got really daring. My nerves really kicked in when I saw the doors being unlocked. My heart began to race.

“You can do this. Don’t be a pussy,” I told myself as I turned the car off, got out, and started walking toward the door. I had my list in hand and with every step I took, certain calm came over me. By the time I walked through the door, I was ready. It took a few minutes to get my bearings but in no time I was looking through the “Misses” section looking for something that matched my list. A very nice sales lady came to help me out and under the disguise of buying a birthday present for my sister, she proved to be very helpful putting a cute little outfit together. She even suggested a ribbon that matched the mesh top. I was all over it.

I decided that my black bra and panties wouldn’t quite work with this outfit. Since I had told the sales lady I was buying the outfit for my sister, I thought asking where I could buy a bra and panty set might be a little awkward. I figured it would be a good idea to head to a different store. It didn’t take long to find a blue bra with a little extra padding in the cup like Missy had suggested and a cute pair of satin panties that kind of matched. Paying for the bra and panty was a little more nerve-racking than the outfit but the lady at the counter didn’t even raise an eyebrow at what I was buying. Proud of my purchases and new found confidence, I power walked through the mall, out the door and to my car. Mission accomplished.

It seemed like Saturday would never come. I woke up with as much more anticipation than last time Missy made me over. I had packed a bag to take with me. I had a pair of blue shoelaces for my gym shoes that matched the skirt I bought. My plan was to swap them out when I got to Missy’s house. I waited for 11 AM and called. Missy told me the coast was clear and that I could come over whenever I wanted. I told her I’d be there soon.

Missy had her radio playing music when I got there and much like last time, her makeup was out and she was ready. I had shaved that morning and was sure it would pass Missy’s test. She unpacked my bag and seemed to be mildly impressed by my shopping. She was especially complimentary at the thought to buy a new bra and panty to match the outfit. She laid everything out on her bed which curiously had a few bikinis and two one-piece swimsuits on it.

“Are we going swimming?” I asked with a laugh.

Missy turned quickly and looked really serious.

“OK. First of all, from this point forward, you are Jenni. You need to work on your voice and how you act. You never know where you will be or who you will see. Don’t wait to start. Second, we’re not swimming but we are going to lay out on the deck to get some sun. I think either of the one-piece suits should work for you. Plus, the tan lines won’t be as noticeable.”

“Are you sure that’s a good idea? I mean…” Missy cut me off.

“Our patio has the bushes around it and the Johnson’s are gone for the weekend as well. I know he’s a peeping tom but he and his wife left yesterday. We’ll be fine.”

Missy sat me down and started with light makeup including a little lip gloss, mascara and focused on prettying up my hair. I sat on her chair, in a pair of shorts while she was doing my hair, looking at the swimsuits. Part of me was hoping they wouldn’t fit. It was one thing to play dress up in the house it was another to lay on her deck to get a tan.

“I see you eyeing swimsuits. I think the silver and pink one will fit you fine but I think you should try one of the bikinis first. They are much sexier. And let’s get something out there. I’ve seen a dick before. OK? I’ve even touched one. And I’ve given Pete plenty of blowjobs. You’re going to have to hide your thing, so I’m just saying. I can help.”

She smiled as she kept working on my hair. I could feel myself completely blushing.

“You’re cute when you get embarrassed. Just relax. Remember last time? Where is confident Jenni who hung out with her friends all night? Instead of hanging with them, you get to hang with me.”

She was right. I’ve wanted this to happen all summer long. School will start next week and who knows what the year will bring. I needed to relax. Missy was done for now. In just under 40 minutes it was an amazing transformation, even just to go lay out and get some sun.

“So do you want to try on a bikini? You are pretty tan already but it may leave some lines.”

“Maybe I should try one on for fun. I can always change.”

“That is awesome,” she said with a definite excitement in her voice. “Ok, let’s go with this black one.”

The “black one” she was referring to seemed to have quite a few strings but it did look like it had enough fabric to help conceal my penis. She was tying them off at the sides and told me to drop my shorts and held them out to me.

“Are you sure this is ok?” I let my shorts fall to the ground and was standing there completely naked in front of her. I took the bikini bottom from her and started to step through to put them on. Her eyes locked in on my penis.

“Nice dick. Or should I say pussy?” as she broke out laughing. I may have smirked but before I could laugh along, she was busy pulling the bottoms up to my waist, tightening the knots over each hip. I felt the fabric tighten up on my ass as she tied the strings tighter. The fabric was covering most of my ass but the bottom of my cheeks was exposed a bit. It felt incredibly sexy. I started to turn to look in the mirror but with no warning, Missy’s hand reached right down the front, grabbed my penis and more or less stuffed it down between my legs under the fabric.

“If I told you I was going to do that, we would have been here for an hour. You can adjust it appropriately but do you see how you can hide it? Just don’t get all horny on me. Boners don’t do well in bikinis.”

I was now turning and admiring how it looked in the mirror. I also had a decent feel on how to keep my dick in hiding. Missy helped me with the bikini top, tied it for me, and stepped back to admire her work.

“Adorable, again. God damn, you have a nice body for a guy.”

Missy pulled her t-shirt off revealing a red and blue bikini top. While my cups were relatively flat, Missy had perky little tits that filled her bikini out nicely. She grabbed two towels off her dresser and told me it was time to tan. I was once overcome by that same giddy feeling that I had months ago. Jeremy was again long gone and Jenni had arrived. I followed Missy downstairs. We each got a glass of water and headed to their deck.

Missy was right, the large evergreen bushes did provide a nice natural barrier. With her nosey neighbors gone, laying out to get some sun should be nice and relaxing. We both put lotion on and laid out on the lawn chairs she had already set up. I admired the way my body looked and how unbelievably sexy I felt. The fabric of the bikini clung to my body in a way that I’ve never felt before. I was very conscious of my package but I had tucked it away pretty good and I wasn’t worried about that at all. I took a nice deep breath and enjoyed the sun for a moment.

“Thanks, Missy. You are an incredible friend.”

“No problem. People would probably think I’m weird or something even helping you do this. But it’s fun for sure. So can I ask you something?”

“Sure.”

“Do you think you may like boys at all? Or have you even thought about what it would be like to kiss one or even do something else?”

“Like give a blowjob?”

“Ok, like give a blowjob, sure.”

“I never would have thought about it before but now when I’m hanging with guys, I start think about dressing like a girl and suddenly my mind starts to wander. And right now as we’re talking about it, I think I would kiss a guy, or maybe even more.”

“Stay right here. I want to show you something.” Missy got up and ran into the house. There I was laying out in a black string bikini on a beautiful sunny day and for some reason, it felt great. Six months ago I would have never imagined this was possible much less actually done it. But here I was, as relaxed as you could imagine soaking in the sun.

Missy emerged from the house a minute or two later with a few things in her hands including a jar of nail polish, some accessories, and what definitely looked like a dildo. I had seen pictures and videos of dildos before but this was my first experience seeing one in person. Missy put everything down on the table next to me, sat on the edge of the recliner next to me, and put the dildo right in front of my face. The dildo had very striking resemblances to a real 6-inch penis, just missing the balls. It looked pretty real.

"So, if a real dick was right in front of you like this, could you resist the temptation? Or would you want to suck on it?” Missy asked.

I looked left and right to see if anyone might be watching.

"Do you want to suck dick or you don’t. It shouldn't matter who is around, Jenni,” Missy said moving the dildo closer to my mouth. I leaned forward to take it in my mouth.

“Close your mouth a little and let your lips feel the head of the dick enter your mouth. Once the head passes your lips, take your tongue and circle the head a few times. Taste that cock and make the guy you’re sucking know how much you love his dick.”

Letting my inhibitions down once again, I did as Missy instructed, slowly taking the head, pausing to suck a little and allowing the head to find my tongue. I leaned forward in the chair and closed my eyes. Missy fed me inch by inch and I sat there imagining a man was standing in front of me and I was there to satisfy him. She slowly withdrew back to the head before feeding it to me again, giving me at least four inches into my mouth.

“God damn you’re a good little dick sucker, aren’t you? It looks like you’ve done this before.”

I got lost in the moment. My eyes closed, I let my mouth and tongue explore, imagining it was in fact a real cock in my mouth. Missy was slowly feeding it to my mouth, in and out at a perfect pace. As I started to get into it, I could feel myself getting hard and my own dick starting to fill the bikini. After another minute or two, I had a raging hard-on. I opened my eyes to see Missy looking straight down at my fully erect cock, one hand feeding me the latex cock, the other had slid down into her own bikini to play with herself.

“Just keep going. You’re doing great!” she said as she sat down on the recliner next to me. Her skin again mine absolutely made me crazy. I could see her really starting to get into things as well. The pace and force of her feeding the cock into my mouth quickened. I could now start to feel the head of the cock against the back of my throat as I was gagging.

“Take it like a good little slut, Jenni!”

Missy took my hand and put it down her bottoms, guiding it to her wet pussy. Her other hand went behind my head forcing my head forward on the cock. She whispered in my ear, “Make me cum.” Two of my fingers slid into her pussy and I began to finger her in unison with her fucking my mouth with her dildo.

“Whatever you do though, don’t cum. This isn’t about you and that hard cock.”

The two of us leaned into each other and I could barely control myself as I felt her bikini-clad breast rub up against me. Her forceful pace continued for another minute before her hand left my head and slid down to my bikini. She slowly started rubbing my rock-hard cock over the black fabric. The two of us were both quietly panting and really into things when I felt her cum all over my hand. Her hand now slid under the fabric and took hold of my now pulsating cock. She pulled the bikini aside exposing my erection.

“This is the first and last time I want you to cum today. Do you understand?”

I nodded my head in agreement as she took the dildo out of my mouth and set it aside. She repositioned herself while holding my cock in her hand. Without any warning, her warm mouth and lips engulfed my cock. I thought about my cock sucking tutorial and could feel her emulating the same method move for move. The ease at which she swallowed my entire cock was amazing. She released her mouth and lips from my cock and started licking down the shaft.

“Now part two of the lesson. How to properly suck on a pair of balls.”

She took my sac in one hand and forced both of my swollen nuts in her mouth, her tongue moving over them rapidly. She released both but quickly gave each a good work over before licking back to my head which had pre-cum starting to ooze from the tip. She licked across the tip before attaching her mouth back to my cock. It didn’t take more than three or four times of her lips working up and down my cock before I was exploding a wave of cum into her mouth. She licked around the tip before making a point to show me that she had swallowed all of it.

“Part three of the lesson. Always swallow.”

As aroused as I was a few moments ago, my cock was once again lucid and needed to be tucked away. Missy handed me a bottle of water, adjusted her chair, and laid back down.

“OK, let’s get some sun now. I’ll do your nails in a little while.”

I adjusted my bikini and closed my eyes feeling the warm sun on my skin. What in the hell just happened? I kept repeating that question over and over again.