John to Jen by Jen Anders jenanders2001@yahoo.com
This is a work of fiction. Any similarity to real persons, places or events is strictly incidental.
My name is John Anderson and I wanted to tell you a little about my life and me. When I was about 13 I started getting really interested in girls. Only I wasn't interested in them in the same way as other boys my age. You see I have an older sister Julie, who was 15 at the time, and was always wearing very pretty, feminine clothes. I also have an older brother Jim, almost 17 at the time, who always seemed to date the most beautiful girls in school. And all I could do was envy the attention lavished on the girls, my sister included, by my parents. I felt like a disappointment to my folks.
The problem was that I was small and skinny and not very good at sports or school, unlike my siblings. My parents were always going on about Jim this and Julie that. After a while it seemed that no one even knew I was around. In fact, most of the time I could do anything I wanted. Especially when Jim or Julie had something going on at school. My parents often left me at home as I showed no interest in these activities. That's because my favorite activity was right at home.
You see, I had discovered my sisters clothing. She and I were close enough in size that I could wear almost all of her clothes. Whenever I was alone I would spend as much time as possible playing dress-up in my sisters frilly panties, bras and dresses. I cherished my private time and eventually began to wear some of her panties to school. I even started growing my hair out to shoulder length.
I was always very careful to keep my secret, as I knew that I would probably be beaten up if any of the other boys found out. The bad things about secrets, is that eventually someone finds out. This happened in the most predictable way. After gym class one day I was the last one back to the locker room and saw Tim Andrews sitting in front of my locker. He said that he mistakenly opened my locker, which is right next to his. Apparently I had forgotten to lock it up before heading out. I was mortified! He asked me if the panties inside were mine. I was so terrified I started to cry. The next thing I knew he was hugging me and said, "It's ok. I understand." He let me go and pulled open the fly on his jeans to show me his own lacy white panties! I was stunned to say the least! The next thing I knew he was asking if he could come over to my house after school. I was still a little out of sorts, but agreed. He gave me one more hug and left me alone to get dressed.
After school, we met in front of the gym for the short walk to my house. When I got home it was empty, as usual, what with Mom and Dad still at work and Jim at football and Julie at Theater practice. Tim and I went up to my room and sat on the bed and talked about school for a bit. Finally he asked, "So... do you always wear panties?" "Not always." I replied. "But I do it quite a lot when no one else is home. How about you?" "Every chance I get" he said. " I also wear my Mom's dresses now and hen but they're too big for me yet." I told him I liked wearing my sister's clothes. He immediately wanted to try them on saying he had always admired the way she dressed so feminine.
We were in my sister's room in a flash. I picked out my favorite, a flowery dress she got for her 14th birthday party. Tim chose a bridesmaid dress from my aunts wedding. It was a little longer than knee length and had a pair of matching 3" heels. I "borrowed" a couple pair of pantyhose and a pair of my Mom's white heels and we dashed back to my bedroom. I dressed first and Tim helped me zip up the dress. I loved the feel of the nylon and lace swishing against my nylon clad legs. The heels I borrowed from my Mom fit perfect and had a sexy 4" heel. As I spun and modeled for Tim he sat speechless. After a bit he said that had he not known it was me, he would have thought I was a girl, a pretty one at that. I blushed and said thank you.
Now it was his turn. The fit was a little snug, but not bad. And the shoes were a little tight but he said it was comfortable enough. Once he was dressed I was impressed with the way he moved in the dress. Very natural and feminine. I suggested a little lipstick and soon we were sitting at my Mom's dressing table primping and making kissy faces at each other. "I wonder what it would feel like to kiss a girl?" I said. This was something neither of us had done. Tim suggested we kiss each other. "After all, we're both wearing lipstick so it shouldn't be much different than kissing a real girl." Actually the thought was kind of turning me on, so I agreed, but suggested we go back to my bedroom.
Back I my bedroom we sat on the edge of the bed and looked at each other. I was starting to chicken out when Tim reached up and stroked my face. Suddenly, I wanted nothing more than to kiss him. I leaned in and gave him a little peck on the lips. The look in his eyes after that kiss convinced me he had enjoyed it as much as I had and was and was eager for more. Soon we were lying on the bed and making out with abandon. Our hands were rubbing all over each other and our legs were rubbing against each other. My cock was harder than it ever had been. Unfortunately, we had to get back into our boy clothes before my family got home. That night I rubbed my little cock until I came all over myself.
Tim and I did this at least twice a week for the next few years. Though we never went any farther than kissing. Shortly after my 16th birthday my parents went to Europe on vacation and I came home to find my sister sitting in my room. She asked me to come in and shut the door. Once inside she came straight to the point. She asked me how long I had been wearing her clothes. I denied it, of course. That's when she opened my bottom drawer and uncovered my secret stash of panties I had stolen from her over the years. While standing there thinking of a response she reached into her purse and showed me some pictures she had taken of me. Apparently she had hidden a camera in my closet. I was busted and I knew it. I blushed and admitted to everything. Except Tim. Then she showed me pictures of Tim and I kissing. She was sneaky this sister of mine.
"So... why do you do it?" She asked "Are you gay?" "I don't know." I replied "Maybe. I still like girls though. Maybe it's just that girls don't like me. Maybe when Tim's dressed like a girl I can forget he's a boy and pretend he's my girlfriend. Maybe I want to be someone's girlfriend. I just don't know." Then she suggested that I dress up for her. I was skeptical until she said that I could be her pretend little sister. So we went back to her room and she helped me try on several of her outfits and I helped her change into some of her sexier clothes. All this dressing up was starting to get to me I must admit. And my sexy sister getting changed with me in the room didn't help. After deciding on an outfit for me, a sexy mini-dress and heels with a matching garter, stockings and bra. She chose a similar outfit and then sat me down at her dressing table to apply makeup and do my hair. It didn't take very long and I was completely unrecognizable as a boy. Only one thing was wrong. I had no tits! She solved this by stuffing some extra pantyhose into my bra. Now we were a couple of hot babes ready for a night out on the town, so to speak. To my horror, I was right!
Just then the doorbell rang and Julie grabbed my hand and pulled me to the door. She explained that her boyfriend had a cousin visiting from out of town and had to find a date for him at the last minute. None of her friends were available tonight and I was the only solution to her problem. Tonight my name was Jen and I was 18. Before I could object she opened the door and let in her boyfriend and his cousin. Luckily Brad, her boyfriend, didn't seem to recognize me and his cousin, Dave, was actually cute.
We were going to a local club for the night. I was terrified! All the way to the club I didn't say a word. Once there we found a table near the dance floor and Julie and Brad immediately hit the dance floor. After a few minutes of total silence Dave asked if I wanted a drink. I agreed, thinking maybe I could just get intoxicated enough to lose some of my fear. Sure enough, after 3-4 stiff drinks I actually agreed to dance a few songs. Dave was a good dancer and very nice, so I soon felt very at ease with him. Then a slow song came on and as we danced I could feel his strong hands on my back and occasionally caressing my ass. I looked up at him and as we gazed into each other's eyes I suddenly wanted him to kiss me. He did. Very softly and tenderly. I was hooked. All I wanted was to kiss him. He made me feel so desired.
After the song, my sister excused us for a trip to the ladies room. Inside she asked me if I was enjoying myself. "Absolutely!" I gushed. "Dave is so nice and cute! Your friends really missed out." "Well, I have a favor to ask." She said. " Brad wants to go make out in his car. Do you mind?" "No." I said. "But what about Dave and I?" "Well, Dave wants to take you out to the car, too. I guess he REALLY likes you." I blushed. After all, it's not everyday a "girl" hears such a nice words.
After collecting the guys we made our way out to Brad's car and drove to a secluded spot in the country. All the way out Dave and I kissed. I repeatedly had to stop him from grabbing my "boobs" or trying to touch my "pussy". I didn't want to spoil his night or mine. After we stopped I was having a real problem with Dave's hands. Julie had a heck of a solution to that problem. Right before my eyes she started going down on Brad! After all the making out Dave and I had been doing he was obviously ready. His cock was making a very large bulge in his jeans. I started rubbing it and soon had to see this monster for myself. As I unzipped his jeans and reached for his cock he helped out by lifting his ass and sliding them down. I gasped when I saw it. It was at least 8" long! Mine was a measly 5" long so his was HUGE! As I stroked it Dave moaned and pushed my head lower. I stuck out my tongue and licked the tip. Dave gasped and I stuck his cock in my mouth. I had never felt so slutty. I LOVED it! I began to savor the feeling of his hard dick in my mouth. I must have done something right. Before I knew it he was pumping up into my mouth and spraying my throat with his hot come. It was delicious!
As I sucked the last of his come off his wilting cock I heard my sister say, "I never knew you were so naughty, Jen! Or so good at giving head. I'm impressed!" I blushed and said, "Thanks, I'm just a natural, I guess." "I'd say so." agreed Dave. I kissed him and soon Brad had Julie and I home. Luckily for me, Jim had gone to bed already, so no one saw us come home.
Back up in Julie's room Julie hugged me and thanked me for helping her out with Dave. "No, thank you, Julie! I had so much fun tonight!" "I guess. You and Dave were obviously getting along great." She said with a wink. "I just wish I could've gotten off too." I said. I'm kinda sore right now, if you know what I mean." "Oh, does Jen have a case of blue balls?" she giggled. "Yes, I do. And now I have to go back to my room and take care of it." "No you don't." Julie said with a grin. "She pushed me back onto the bed and lifted my skirt. Before I knew what was happening she had my cock out and was sucking it with abandon. She was great at sucking cock! I was deep into having my cock sucked when a voice said, "What's going on here?" Julie and I looked over and there was Jim!
Jim strode into the room and saw everything. Julie started crying and I hung my head in shame, my cock deflating instantly. Jim obviously didn't know what to say, but his body knew what it wanted. His boxers were tented something fierce! He knelt next to Julie and hugged her while saying he wasn't going to tell anyone. Then he looked at me and said' "What's your name?" I lowered my eyes and said "Jen." "My, what a pretty young lady you are, Jen. I can understand how Julie would be attracted to you. I know I am." I was speechless! Was my own hunky brother coming on to me? He stood up and approached me as Julie composed herself. Before I knew it Jim was kissing me and pushing me back on to the bed. Julie having recovered her composure undressed then helped me out of the mini-dress I was wearing. Jim stood back to take off his boxers and Julie got into a 69 with me on the top. As I tasted my first pussy, I felt a warm, wet sensation around my asshole. Jim was making me feel awfully good with his probing tongue, but I was unprepared for what came next.
After he had gotten my tight little pucker all wet and slippery I felt something HUGE pressing at my ass. I looked around and was stunned by what I saw. Jim was as big as I was small. Easily 9" long and 21/2 " thick. I later found out it was 9 1/2" long. All I knew then was it wouldn't fit in yet. Julie said he had a solution. She went to her dresser and came back with a slim vibrator and some KY. Jim applied some to my ass and worked the vibrator in to my ass. I was in heaven. Meanwhile, Julie began sucking Jim's cock and was fingering herself like mad.
After a few minutes of this Jim decided I was ready and pulled the vibrator from my ass. Julie applied a fresh coating of KY to his cock and guided him in. My ass may have been loser now, but Jim was a BIG boy. I thought he'd never get it in but then the head went in with a slight popping sensation. I never thought he'd get any more in. He had different ideas. As he slowly pumped back and forth he kept going deeper into my ass. Julie crawled back under me and we resumed our 69 with abandon, although I must admit it's rather difficult to concentrate on eating pussy when you're getting your ass fucked and your cock sucked. Soon, Jim was pounding his full length into me and I had abandoned all pretense of eating Julie's pussy. It wasn't too long before I felt Jim unloading into my quivering ass. Almost simultaneously I came in Julie's mouth. She swallowed as much as she could, but I had a rather large load built up from earlier that night and she got it all. I squeezed Jim's cock with my ass, milking it for every drop of come. When he finally slipped from my abused asshole, I could feel his spunk running down my leg. Poor Julie still hadn't come though. I remedied that situation soon enough by diving back into her dripping pussy. I soon had her screaming in orgasm all over my face. We all passed out on Julie's bed that night, snuggled up into each other.
The next morning, I woke up last and showered. When I got down stairs Jim and Julie were talking over breakfast. I sat down and they told me that they were wondering if I felt ok after last night. I assured them that I felt great. I loved them both and that I really hoped we could do it again. That's when they told me they had already made plans for me for the next two weeks until our parents got home. They had called Tim's parents and arranged for him to stay over for the next two weeks. I was surprised to say the least! Then they told me we had to go shopping. Apparently I was to get my own clothes! What a wonderful idea! I ran upstairs and started getting into some jeans when Jim stopped me and said that "Jen" would be shopping today, not John. I tried to object, neither Jim, nor Julie would hear of it.
Julie led me back into the bathroom and proceeded to cover me in hair remover. Before I knew it I was left with only a small thin patch of hair above my small penis and that was it. Julie then led me back to her room and helped me into a very pretty sundress and low heels. Then a dash of makeup and we were ready. I was as nervous as a cat, sure that the neighbors would recognize me in the broad daylight. No one even looked twice.
Our first stop was the beauty salon. I was to receive a full makeover and a perm. Not to mention a manicure and a pedicure. Soon, I was looking absolutely fabulous! I had long nails and my shoulder length hair was perfectly styled. I felt radiant! And none of the ladies that worked on me ever suspected I was really a boy. Next stop, the MALL!
I was really starting to get into this. At the mall I walked past several boys from my school and while none of them recognized me they all gave me a good long look with lustful eyes. We went to Victoria's Secret and I picked out several bra and panty sets, as well as numerous nighties and other feminine undergarments. Next were a dress shop, a trendy clothing shop and a shoe store. I even got a bikini! Soon I was almost overloaded with packages and Jim's credit card was nearing its limit. Once we got home I saw what Jim had bought while Julie and I were at the salon. He had gone to the local porn shop and bought a strap-on for Julie some breast forms for me and a few other goodies. Including several butt-plugs.
Julie and I decided to put on our bikinis and lay out by the pool while Jim worked out. Julie and I had a great time, chatting like girlfriends and giggling. I eyed her body and commented that I had always thought she was the most beautiful girl in school. She smiled and gave me a kiss. I rolled over and rubbed her breast as she slid her hand down the back of my suit to play with my asshole. I was getting pretty worked up when she told me to wait. She skipped back into the house and was soon back wearing the strap-on Jim had bought her. It was almost as big as Jim! It's a good thing we had a privacy fence. She strutted over to me, pulled me up and bent me over the picnic table. With a generous dose of baby-oil she greased up my tender ass and was soon pushing her new "cock " into me. I moaned and wiggled my ass to get it farther into me. Soon she was hitting bottom and was fucking me for all she was worth. I pushed back and we soon were coming all over ourselves.
Jim had watched the entire show and he was applauding from the doorway. "You handle that cock like you were born with it, sis." She smiled at the praise and said, "You look like you need some help. Gazing at his stiff cock, I grinned and motioned for him to come over to me. Soon I had his cock buried in my mouth and was greedily sucking his cock. All this sex had my young cock stiff as a board so I pulled Jim down to the deck and got into a 69 with him. He was reluctant to suck me at first but soon got into it. Not as good as Julie, but definitely good. A shadow fell over us as Julie knelt between Jim's legs and rubbed baby oil into his ass. After a weak protest from him, Julie had a couple fingers in his ass and was loosening him up nicely. He was wiggling his ass and was ready for more. Julie lifted his legs and I helped her slide her tool into his willing ass. Jim gave a grunt, but otherwise made no sound until Julie was completely in his virgin ass. After a minute for him to get used to it Julie started a slow stroking rhythm as I resumed sucking on his raging hard-on. He apparently really got into it because he started sucking me with abandon. I didn't last long and he and I came within seconds of each other. I couldn't drink it all and it started leaking out of my lips. I saved some for Julie as we kissed. Julie pulled her sloppy dildo out of his twitching ass. He looked well satisfied with my come on his lips and his leftover cum dripping down his shaft. Julie quickly cleaned this up and shared it with Jim.
Now we had to hurry and get ready, Tim would be here soon. Julie and I went upstairs to fix ourselves up while Jim took a shower. I put on a sexy pair of skintight hip huggers with a halter- top that showed a little tummy with a pair of high-heeled sandals and Julie wore a slinky little mini-dress with a pair of 4" heels. Jim was dressed in khakis and a polo. All of us then put in butt plugs in anticipation of the fun we might have that night.
Tim showed up at 7pm and I was upstairs waiting for the proper moment to re-introduce myself as Jen. Jim let Tim in and said I'd be down in a minute and that dinner was almost ready. Tim asked where my parents were and Jim lied and said they were out for a bit, but would be back. Not really a lie, but not really the truth. Julie came in and Tim commented on her outfit. She said she had a night out planned but it wouldn't start for a while yet. That was my cue. I came down the stairs as gracefully as I could and almost laughed when I saw the look on Tim's face. Boy, was he surprised! I walked over and kissed him deeply. And explained that both Jim and Julie knew our secret and were cool with it. Jim then pulled out my chair for me, Julie and Tim. Tim was obviously still a little uneasy with it and didn't say much all through dinner. After dinner Julie and I took Tim upstairs and began his transformation into "Tina".
Julie helped him with the hair removal just as she had done for me, and then the makeup. Since Tim's hair wasn't long enough for styling we used one of my Mom's wigs. I then helped him into the outfit I bought just for him that day. A short skirt and a silk blouse with a matching garter, panty and bra set. Once he was dressed he was stunning. I kissed him and told him he was beautiful and that we had one more surprise for him. That's when Jim came in and asked if his date was ready. Tim stammered that he couldn't possibly go out but then the doorbell rang. Brad and Dave had just arrived! We all piled into my parents Lexus and went to the same club I had gone to the night before. I knew what "Tina" was going through and squeezed her hand. She smiled at me and then we were at the club. After a round of drinks all of us went out dancing. Dave said I looked even sexier than the previous night. It's nice to be adored. He smiled and pulled me close. I looked over at Tina and she wasn't comfortable yet, but was doing all right. After a few more drinks a slow song came on and Jim and Tina followed us out on to the dance floor. Jim pulled Tina into his arms and she leaned right in to him. The next time I looked over, Jim was kissing her and she was obviously enjoying it. All of us girls then went to ladies room to "freshen up". Once inside I mentioned that Tina seemed to be enjoying herself. She said, "I am! I can't believe I'm out on a date with a cute guy like your brother!" "Just wait," I said, "The fun is just starting."
Once we got back to the guys we all decided to head home. Julie and I were busy making out with our dates, but decided not to invite them in. After we all got inside. I led the other girls upstairs to get into something more comfortable. Jim meanwhile had poured some wine and brought it upstairs to the bedroom. By the time we got to the bedroom he was already in the bed waiting for us. Julie went to get some toys and Tina and I got in bed and started making out. Jim started kissing Tina and I kissed my way down to her cock. It was long and stiff and I sucked on it greedily. I soon worked her into a 69 and she got into sucking my cock as much as I was into hers. Julie had come back by then and had already donned her strap-on. She climbed behind me and lubed me up. Then handed the KY to Jim. And he prepared Tina by working the lube into her ass. She moaned around my cock and soon had Jim's cock pushing into her ass. I had Julie fucking me in a steady rhythm and Jim was almost completely buried in Tina. Soon we were all getting into a good fuckfest. Before I knew it both Tina and I were spraying our loads across each other's faces. We spent the rest of the night fucking and sucking in every possible position and everyone ended up sleeping in a pile on my parent's bed. We kept this up for the next two weeks with Tina and I becoming more feminine every day.
I lived a double life for the next 2 years until I graduated and could move out on my own. Tim moved in with me and we live as women full time. We have many boyfriends, but always make room for Jim and Julie when they want to visit.