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My First Boyfriend - Part One

Tags: young, bi, oral, anal,
I learn to cross dress and get a boyfriend
Since my family had moved to our new house, Steve and I had become best friends. He lived next door and had moved in about a month before we did. With both of us being the new kids on the block we bonded quickly. He was two years older than me at eighteen and I had just turned sixteen a few months back. He was also taller and had more muscles than I did. He had tan skin and black hair where I was pale and had brown hair. He stood almost six feet tall and I was about five foot six. We played ball, fished, rode our bikes, and did all the things boys our age did, including smoking and when we could, drinking.

During the early part of summer we had constructed a fort to hang out and smoke in. Steve had a very large back yard that was mostly wooded and his property sat on a hill. We used shovels and dug into the side of the hill like we were digging a mine. Digging was hard with the red clay we had in Georgia but it was ideal for making tunnels that would not cave in as easily as other soil. We even used two by fours to brace the walls and ceiling as we dug further in. Once the digging was done we took scrap plywood and made walls with shelves and a ceiling. We took a scrap piece of carpet and lay it down for a floor and stuck some of those battery operated lights to the ceiling. We hung another piece of carpet as a door. The fort was big enough to fit four or five people in a sitting position and since we didn't clear the brush and bushes out before digging it could not be seen unless you were right on it.

We spent many afternoons in the coolness of our fort and smoked cigarettes and played cards. One day we were sitting in the fort with the door flap open watching the few cars that drove by, when a guy in an old Chevelle pulled over right in front of us. We watched as the driver went to the back of his car and opened the trunk. He took out three large trash bags and tossed them into the brush before getting back in his car and driving off.

We waited till he was out of sight and went down to check out what he had dumped. We had talked before about a friend of ours who saw someone throw a package out of a moving car right before the cops pulled it over. He had picked the package up to find it was full of cocaine. He had a great time for a while off that! I don't know what Steve was thinking on the way down but I was hoping for three huge bags of weed! We got to the first bag and untied it. There were bras, panties, dresses, skirts, hose and all kinds of other women's clothing. We opened the other two bags and one had lots more women's clothes while the third had shoes, make up, wigs, and at the bottom were dildos, butt plugs, anal beads and some other sex toys. I’ve since come to realize it was a cross dresser purging his collection. Lots of CDs do this just to go back to cross dressing and buy a new collection only to purge again later. It can become a cycle with some people.

We both acted disappointed and called the guy a fag but deep inside I was very turned on by it. Just the feel of the silky lingerie made me get hard and I could swear Steve had a bigger than usual bulge in his jeans too. We left the bags where they were and decided to go home. Steve said he was hungry and I said I wanted to go home for lunch too. That’s what I said but I was so turned on I knew that I was going to go home and use some of my mom’s panties to jack off.

I ran upstairs as soon as I got home and snuck in my mom’s drawer to get a pair of panties. I went to my room and stripped off my clothes. I slid the panties up my legs and over my butt cheeks. They felt so feminine and sexy! I rubbed m cock through the panties and came inside them unexpectedly. I had intended on taking them off or at least pulling them down before I came but it was too late. I took them off and stuffed them under my mattress.

I made a sandwich and sat in front of the TV to eat. I lost track of time and soon my mom was home and soon after it was dinner time. After dinner I watched more TV and before I knew it, it was bed time. I lay in bed thinking about all the panties and stuff in the bags. I was horny beyond belief and wanted more than just jacking off. I decided to sneak out and go check out the bags again. I climbed out my window and headed for the fort. I stopped and rummaged through the bags until I had found a nice bra, panties and some stockings to wear. The bra was black and lacy and the panties were silky bikini style. I headed up to the fort and as I approached could tell that someone was in there. I could see light escaping around the carpet door and could hear something strange.

I crept up to the door on my hands and knees and peeked through the opening. I was shocked, scared, and oh so turned on by what I saw! Steve was in the fort wearing a blue bra and panties and jacking off. I had never seen his cock before and could not believe how much bigger it was than mine. I was about 5 inches hard and he was at least two inches longer and what amazed me was the fact that is was so thick and was uncircumcised. I watched him stroke his cock and loved the way his foreskin would roll over his head then pull back to expose his head each time he stroked it. I think that this was the exact moment I became a cock lover.

My cock was so hard it actually hurt. I had to get some relief! I stripped off my clothes and put on the bra and panties. I left the stockings for later. I was trembling as I pulled back the carpet door and crawled in. Steve was in shock at first until he saw that I had on lingerie too. His cock had started going soft already. He said, "Man you scared the shit out of me!"

"It looks like we both had the same idea," I replied.

"If you ever tell anyone about this I'll kick your ass!" he said.

"Don't worry! I'm wearing the same shit too!"

He started stroking his cock again and I sat down and leaned against the wall next to him. I pulled out my rock hard cock and started stroking. We watched each other jack off until he tightened up his grip and shuddered as he released a huge load of cum. As soon as he started cumming I did too. I noticed that while I came in spurts his was more of a steady gush, and there was a lot more than mine. We got the three bags and brought them up to the fort and left them there, then went back home.

The rest of the summer we snuck out every night to go to the fort and cross dress and jack off. We experimented with all the different outfits and tried the wigs and make up. Before long we knew how to make ourselves look pretty hot. I especially looked like a girl since I was petite and developed late. I was naturally hairless and only had a wisp of hair on my genitals. In fact if I was tucked I looked like a well groomed girl. Steve was more masculine though and all his muscles make him look like a guy in drag. I didn't mind though, in fact I thought he looked hot.

One night when we had snuck some beers out and were buzzed we started jacking off like usual, we would lay next to each other and jack till we got off. This night we somehow switched hands so I was jacking him and he was jacking me. We didn't speak about it, it just happened. I was amazed at how much cum he shot and how warm it felt on my hand and I loved the way his big cock felt in my hand.

After that we never jacked ourselves; I jacked him and he jacked me. One night we were jacking each other and Steve came much earlier than usual. I had jacked myself off earlier that day when Steve wasn’t around so it was taking me longer to cum. Steve rolled over on his side facing me and began sucking my nipple while stroking me. It turned me on a lot and I moaned like a girl. Then he kissed me and put his tongue in my mouth. I immediately responded and we started making out. His hands were all over me and I loved how it felt to have him treating me like a real girl. When his finger found my little pucker hole I came immediately. We lay there for a few minutes cuddling together before going home. On the way out Steve kissed me passionately with his tongue in my mouth and gave my ass a little squeeze. I went home and slept in a pair of panties and bra feeling like a real girl.

The next afternoon before I headed home for dinner Steve gave me a little brown bag and told me it was something special for me and to open it before coming out that night. After dinner I went to my room and opened the bag to see what was inside. It was one of those disposable douches. My cock twitched at the thought of using such a feminine product and I was very curious about what Steve had in mind for me. I had tried using my finger and some other small objects in my ass before and found it to be very pleasurable so I was hoping we would fuck. Later on when everyone was getting ready for bed I pranced down the hall to the restroom and used a douche for the first time. I had already showered and made sure I was clean there so all I needed to do was clean the inside. I removed the plastic bottle from the box and while lying in the tub inserted it in my little hole. I squeezed the contents into myself and long story short, I was clean and fresh in no time.

An hour or so later I was in the fort in panties and bra putting my make up on. We had put a small table and a mirror in so with the stick up lights on I could see well enough to do a pretty good job. I put on a black shoulder length wig, stockings, a nice black see through nightie, and some black heels. I was surprised that Steve had not arrived yet. I found a half a joint from earlier in the day so I lit it and sat back to wait for Steve.

I had gotten a pretty good buzz going when the carpet door pulled back and in crawled Steve. He was wearing some nice khakis and a polo shirt instead of his normal jeans and t shirt and I could smell cologne. He had with him a single red rose and a bottle of champagne stolen from his parents bar. He handed me the rose and pulled me in for a kiss.

“What’s going on?” I asked.

“Last night was so good I decided I didn’t want to be a girl with you anymore. I want you to be my girl.”

I was stunned and so excited I almost couldn’t handle it. I threw myself into his arms and we kissed long and deep. After the kiss he opened the bottle and with no glasses we sat next to each other and drank from the bottle and lit another joint. Steve put his arm around me and held me close as we smoked a joint and drank champagne. By the time the bottle was empty I was pretty buzzed. We started making out, sucking each other’s tongues and Steve was pinching my nipples and ass the whole time. He felt so strong and smelled so good I just melted into him. I knew I was his to do what he wanted with me and I wanted him to take me like a real woman.

As our kissing grew more heated Steve had his hands all over me, rubbing my ass, pinching my nipples, and nipping my ears and neck with his teeth. The only part he did not touch was my little cock. He slid his hand down the pack of my panties and found my puckered hole. He slid a finger in and I gasped. He wiggled it around and I pushed my ass into his hand wanting more. I started rubbing his hard cock through his pants while he fingered and kissed me. I managed to get his pants undone and fish his cock out. I stroked up and down the length of it, marveling at how his foreskin moved with my hand. He was moaning and groaning and I soon felt precum leaking on my hand. I licked my hand clean and loved the sweet taste of it. I bent over and took his cock in my mouth. I was instantly hooked on cock from that moment on. I loved the spongy feel over the hard muscle core, and the way he tasted and smelled. I can get hard just smelling that musky scent now.

As I learned how to give head Steve kept working his finger in and out of my hole and soon he had two fingers in. He pushed on the back of my head and I almost gagged when his cock hit the back of my throat. I was so horny by then that I wanted to swallow his cock whole so I relaxed my throat and fought the gag reflex and when he pushed again his cock slid down my throat until my nose was pressed into his pubes. He held me there and pumped in and out of me, fucking my mouth like it was a pussy.

I backed off him and started licking his balls. Then I took one in my mouth and gently sucked it, then did the same with his other ball. I licked his head like a lolly pop then took him all the way in again. I tightened my lips around his shaft and started bobbing my head up and down on it. I would pull back until just the head was in my mouth then plunge it back in my mouth. I kept this up until the inevitable happened and he filled my mouth with warm spunk. I hadn’t even thought about what to do but it seemed natural to swallow it. So that’s what I did, I swallowed the whole mouth full and kept on sucking until I had gotten every drop he had to give. He pulled his cock out of my mouth and collapsed onto his back. I lay next to him on my side and started rubbing his chest hairs while I lay my head on his shoulder.

After he started to breathe normal again he turned his head and kissed me again. I returned the kiss and let my hand wander down to his cock. I gently stroked him as we continued to kiss. Soon his cock was rock hard again. He broke our kiss and asked me. “Are you ready for me to make you my woman now?”

I nodded my head yes, and gave him another passionate kiss. He helped me get my panties off and I helped him get undressed. I sucked him for a little then got on all fours in front of him. He rubbed my ass a little and I sort of wiggled it a bit. He put a finger in and asked, “Are you ready baby?”

I looked over my shoulder at him and told him, “Take me now baby!”

I loved it when he took his position behind me and started lining his cock up with my hole. He used his knee to nudge my legs open a little wider and then placed his cock against my hole and held it there. I really wanted him so I pushed back slightly and taking my queue he pressed forward and his cock began to penetrate me. When his head had passed my outer ring he held it there briefly before slowly sliding the rest of the way in. It hurt some and at first I thought he’d split me open but he held it there until I it felt better and I started pushing back against him.

He started stroking his cock in and out slowly at first and then a little faster. Soon he was pounding in and out of me and I was loving it! His balls slapped against my taint on each stroke and I was begging him to fuck me harder. He kept pounding and pounding my virgin hole until suddenly re reached around and grabbed my cock. As soon as he did I shot a huge stream of cum that hit me on my chin. I could feel him flooding my insides with warm cum as I continued to pump stream after stream of cum.

When he had finished he slowly pulled out and his cum started leaking from my hole and running down my balls and thigh. I could feel the cold air inside me since my hole was gaped open. I fell forward onto my stomach and lay there while the cum slowly leaked out of me. When I had caught my breath I crawled over to Steve and licked his cock and balls clean. I was pleasantly surprised when he turned me over and started licking my ass clean. He licked my hole clean then moved down to my balls and thighs and gently licked until they were clean. Then he rolled me back over and took my cock in his mouth. He gently sucked me and it didn’t take long before I shot in his mouth. He held it in his mouth and then gave me a kiss to share it with me. We kissed and left the cum in our mouths as our tongues danced. When we had both gotten a good taste we swallowed and continued kissing gently for a while until we were both satisfied.

After that night we had regular date nights every week where we would make love as a man and woman. One night after our love making Steve asked me if I’d like to have a little honeymoon since we were a couple and had never made love anywhere except the fort. He explained that his parents would be out of town for a few days the next week and he wanted me to stay with him and be his woman the whole time like we were married. I quickly accepted the invitation and the next week we would finally get to experience being a normal couple. I’ll let you know how that went in my next story.

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