Do I really have a female side to me? I would never have thought so until a recent chain of events, which started with my girlfriend Anna and her best friend Rebecca (Becky) showing me the way.
My name is Jamie and I have always considered myself to be strongly heterosexual! I played baseball in high school, and nothing I ever saw among all of those naked butts and cocks in the locker room ever interested me as much as being with Anna.
Anna is pretty—God is she pretty! She is petite and slender but shapely, with good-sized breasts for her small size. Her best friend Becky is a little taller, a little fleshier, and her dark brown hair and eyes, contrasts with Anna’s wavy light brown hair and clear blue eyes. Anna is very quick-witted, where Becky is slower on the uptake and more naïve.
The girls have been best friends since the third grade, and I became their friend in high school. Over the years, the girls shared everything between them including clothes, toys, and boys—and they even shared me until Anna and I became exclusive! We three formed a triumvirate in high school; the three of us against all! As good friends we did everything together.
I know that Anna has gone out on me a time or two … she doesn’t know that I know … but I know! She may be smart, but I am much smarter! Although we were in a relationship, she was still as single as am I, and she can pretty much do as she wishes. It’s the price I pay for my own freedom, but I have never gone out on Anna while we were together.
Both girls have always described me as ‘cute’ and I suppose that I am, but I am also somewhat short at five-foot eight … alright, five foot seven and a half! I am very slight, with what you might consider soft, or even ‘feminine’ features; I was often teased as a ‘pretty boy.’ but that might have something to do with my ease in attracting girls. Friends always told Anna and me, that we were a cute couple. I always thought so too!
I earned both a BS and MS degree in math and computer science while still nineteen. High school was holding me back so I quit during my junior year with an invitation from the university to enter early. The only thing that kept me from being stuffed in my own locker in high school was the fact that I was also a good baseball player, a sport that requires quickness as well as strength, and I had the respect and protection of the jocks. I am still friends with some of them!
So, why did my two girls decide to help me with this? It was partially my doing, I suppose. They talked about going out for another so-called ‘girl’s night out’ soon, and I was worried about what goes on at one of the clubs during their outings.
It’s not that I don’t trust her, but Anna has some secrets; I can hear it in her voice when I have asked her to lunch on occasion and she declined. Becky has always been my truth barometer for Anna though. When I ask Anna something, I always look for a reaction or a ‘tell’ from Becky. Anyway, I grumped about them going out and asked what they do when they are out together. Becky quickly answered,
“The only way to know for sure is for you to come along!”
I saw Anna quickly shoot her a look, but the invitation was out there, and Anna couldn’t take it back gracefully. I tried to give her an out by saying,
“Well I can’t very well go with you guys when you are out on your own! That would be a major buzz-kill for you two! Guess I’ll just have to trust you to be good!”
Becky turned to Anna and whispered something to her and flashed a look back at me. They talked back and forth, looked me over from head to toe, giggled, and then continued their private conference. This was making me very uncomfortable, but then Anna cleared her throat and approached me with their verdict.
“Jamie darling, you are going out with us on our next night out … as a girl!
“Wait! What?” was my less than brilliant, but surprised response!
She put her hands on my shoulders and kissed me sweetly, and said,
“Honey, we are going to make you up, and dress you up. Then you are coming out with us next week dressed as our cute little girlfriend. What you do when you get to there, and what liberties you allow men to take, is quite up to you, pretty boy!
“But, Anna, I…”
She interrupted me, “Jamie, it will be fun; please let us do this to you. We are going to have our own little dress up doll, and take her out clubbing with us. It will work, trust us … you will love it!” Looking me up and down she continued,
“Baby, you have a lot of raw material to work with. You have long blonde hair, and a slight build, slender, nicely shaped legs, and with a tuck-under of your cute little junk, you could be a very popular girl!” I tried to interject,
“But, what if…” Becky interrupts,
“C’mon Jamie, I just know you will love it.” Then she looked at Anna for her agreement and continued,
“We will dress you up tomorrow night to get you used to the clothes, the konya escort heels and stuff you will be wearing. Tonight is Thursday, and we are going out Friday night, next week … and you are coming with us, little girl!”
She put her arms around me, kissed me, I turned to Anna and she did the same thing, and whispered,
“Jamie, please let us do this honey! It will be so much fun!” I was beaten and I knew it!
As I returned to work the next morning, I couldn’t think about anything else, I had to rely on Janet, my second-in-command, to keep project work moving. I had never worn any female clothing of any kind and never cared to, but my sweet girls were going to dress me up. My narrow ass would likely be in panties sometime very soon. I couldn’t say it sounded like much fun, but I did feel some amount of jittery anticipation!
I love Anna and I know she really does love me, but as I said, we are not married so her body is her own to do whatever she wishes when she goes out with Becky. If we go out clubbing as three girlfriends, she would be free to be with someone else; but then so will I, so she takes the same risk as I do.
When I arrived home, I found out that my two little monsters went shopping. I now have a tight little dress to go out in; with bras, panties, stockings and shoes, along with makeup that matches my coloring. These little imps even bought me breast forms … and a garter belt! The girls were absolutely giddy as they laid everything out for my trial run tonight.
We had not planned to go anywhere, so it was just the girls and me at home tonight. Anna laid out my new clothes, while Becky started to undress me. She undressed me completely, and the sight of my cock hardening to about four inches, was too much for her. She slid her fingers over it, touching and tickling it, fingering my balls, and said,
“Oh Jamie, it looks so delicious! I have always loved your cute little prick!”
I told her, “I’m sorry baby! It might be small, but it’s spoken for! It belongs to her (pointing to Anna)!” She started to pout. Anna was seeing this, smiled, and told her,
“Don’t get him too excited sweetie, he will have to be tucked under yet tonight after you make him up!” Anna told her friend.
They took me into the bathroom, and shaved my body clean of all hair everywhere, except my blonde locks up top. They both laughed and giggled as they touched and teased me, but Anna did the shaving. She looked at me with a smirk as the razor neared my junk, but it was expertly and safely done, with little loving touches from both girls.
The cool air on my denuded junk felt funky! Anna applied some soothing cream, running her hands over my smooth cock and tight balls. Then she put some body lotion on my shoulders, arms and legs. It felt so good to have her hands on me!
She reached up under me and pushed my testicles back up into what’s called the inguinal canal, where they naturally retreat for protection, and when they are cold. I could feel what she was doing, and it was uncomfortable at first. Then she tucked my penis between my legs, asking me to hold it in between my ass cheeks from behind, as she taped it in place.
She had asked the lingerie clerk what would work best to hold it in, and ended up buying me a pair of boy shorts a size too small. Then she helped me into them, taking her time getting them into place, and running her hand over my new bulge-free mound to check everything. She said softly,
“Ohhh, baby, that feels so nice!”
Then she kissed me sweetly for being so good and patient. She threw a short cream-colored silk robe with pink trim around me for Becky to make me up. She had everything she needed all laid out. I could feel my manliness slipping away, bit by bit.
“What’s the needle for?” I asked her.
“We bought you some very cute little earrings darling!”
“No, you’re not gonna—”
“Yup! But you’ll be fine! Don’t worry!” she giggled.
She gave me just a quick once over with a little base, something she called a concealer and blush, she did my eyes with a light shadow and mascara, and then a pretty but subtle shade of red lipstick.
She explained how she applied each item, giving me little touches and kisses as she did. When she is finished, she looked at her handiwork with a smile, closed her eyes and kissed me on my soft red lips. Her eyes fluttered open after the kiss and she smiled. I saw what I always saw in Becky’s dark brown eyes and on her pretty face—her genuine sweetness.
Anna helped Becky pierce my ears, and then she did my longish blonde hair in a cute hairdo, soft on top and curled at the edges … very feminine!
Becky smiled prettily said,
“Look at yourself darling, you’re beautiful!” then to Anna, “isn’t she beautiful?”
Anna inspected the job they both did on me, and said,
“Jamie, you look amazing! You really are a pretty girl! Let me get you dressed!”
“Oh I agree honey; you are prettier … konyaaltı escort than … than I am!” Said Becky who is actually very pretty, we all laughed.
I couldn’t believe that she actually bought me a set of breast forms in a bra size to fit my body! They felt nice though … natural. They even had puffy nipples like Anna’s.
They fit very nicely under the thin bra and to my skin, allowing for a natural look and feel and for the nipples to poke through a little. Anna put my bra on from the front so she could taste my lipstick by pushing her lips into mine as she reached around behind me. Then she slid a very short dress over my head and zipped it up the back. It came to just above mid-thigh down below, and just covered my bra strap in the back.
She sat me down on the low stool at the dressing table and helped me on with my stockings, which went nearly all the way up. The four-inch heels completed the picture, and she asked me to walk around in them to get used to them. They were a little wobbly at first, but I quickly got the hang of them.
The three of us went into the kitchen to give me a floor to try them out. Becky put on some music, starting with a slow number, and Anna danced with me. She had to lead, since I would be dancing with men, and would have to get used to the reverse position. Then she slid her hand down my dress, then underneath the hem and onto my ass. I pulled her hand out and said in a very feminine voice,
“Please! I’m not that kind of girl!”
Both of the girls laughed, wide-eyed, with surprise holding their hands over their mouths! They marveled at my realistic girl-voice, and at the attitude. I have a rather high tenor voice to begin with, so I was able to affect a very believable girl’s voice. It didn’t sound like a man trying to sound like a woman, it sounded like Anna’s and Becky’s voices. Then Anna said,
“Oh Jamie! Wow! You’re ready! Now to train you on poise and carriage, you will be our servant-girl tonight and serve Becky and me until we say you can stop. Then you can become my handsome Jamie again, and take care of your horny girlfriend!”
Then I said to Anna, but really to both of them, “I have just one question. If I am going to be a girl, don’t I need a girl’s name?”
“Darling your name is Jamie, and that is already a girl’s name!”
“My name in James, my family calls me Jimmy; it is just the two of you and some friends who call me Jamie!”
“Okay we will come up with one honey!”
They moved away a little, put their heads together mumbled something I couldn’t make out, Then Anna smiled and announced,
“Welcome to the family, Jill!”
“Hmm, Jill! I guess I can live with that!” We all giggled like three silly girls.
“Um Jill darling, can you get me a glass of wine, and a beer for Becky before you make dinner?”
“Yes ma’am, right away!”
I called them ma’am to play the role tonight, but I asked them not to embarrass me when I am dressed like this. I told Anna,
“Don’t get lost in the role honey!”
“Okay darling!” she says sincerely.
The girls had great fun with their dress-up doll (me!), and they were very respectful as I waited on them to develop some balance and poise wearing me new stuff. I made them dinner, and served them coffee, but they helped with the cleanup afterward.
I got a lot of needed practice with my female voice, and movements. I tried not to exaggerate my movements. I didn’t want to come off as a drag queen, so I watched Anna and Becky and did the same things. I now feel more comfortable going out in public this way.
After being relieved of my maid duties, we were all sitting in the living room. The girls decided between them, that they just couldn’t stand not taking me out in public. Anna asks,
“It’s still early, anyone want to slide out to a pub for a beer? I think we should road test our little dolly here to see what she’s learned and to see how people react to her. But I’m not going to get dressed up so Jill will have to dress down a little.”
Becky quickly said, “I have a cute halter top and pair of short short that might fit her. She can wear a pair of her own tennie’s, or maybe lower heels.”
I was soon wearing one of Becky’s halter-tops and a pair of her shorts that were a little snug, and let a little ass cheek peek out the bottom edge. Anna was smart enough to buy me a pair of low heels when she and Becky shopped for me.
“Oh my God, Jill! Your little ass and legs look so good in my shorts! The boys are going to go crazy for you honey!” Becky said, with Anna’s agreement. Anna added,
“Now be a good girl out there tonight, and play nice with the boys!” and she said in a sultry voice, “Good girls get special treats later!”
We all laughed.
The pub was crowded, but we were lucky to grab a table just as another group was leaving. As I squeezed through the crowd, I felt more than one hand on my ass … and one of them pinched konyaaltı eve gelen escort me! I turned and saw the offender with a big smile as he said, “Hey baby!” I turned back with a little smile on my face.
Anna volunteered to get us each a drink since the wait-people were overwhelmed. I sat up straight and pushed my ass out a little as I see some of the women doing. I was excited to see if I could attract some male attention … to see if I was pretty enough! My nerves were jangling.
Becky and I talked excitedly and Anna came back with beers for Becky and me, and a gin-tonic for herself. Anna sat, and I made a limp-wristed gesture to Anna telling her that I will get the next round. She giggled at my feminine gesture and said,
“Okay sweetie, whatever you say!”
Becky looked over at us smiling, but she missed my little interchange with Anna. My pretty girlfriend moved closer, picked up my hand and kissed it just out of affection. This place was big and mostly a sports bar, but they had a dance floor and a small band on the other side. I loved the noisy atmosphere of this place! I thrive on activity and noise whenever I go out … the noisier the better!
Anna grabbed my hand and pulled me over to the dance floor and we did a sort of ‘bop step’ to a lively number. Anna is a better dancer than I am but for a brainiac-nerd, I kept up my end quite well. We had fun and I could see that Becky was enjoying watching us.
I feel someone brush against me, and two young men cut in on us. One on them pulled me into a dance and the other did the same for Anna. They were not great dancers, but they were of the male persuasion, and that’s all we needed.
Mine was tall and nice looking and Anna’s was a little shorter but a better dancer. I was having a great time, and found out something that shocked me. I found myself looking into his face and wondering what it might be like to kiss him. Dressed the way I was, wearing panties, and all made up, I found that I had urges I would never have as Jamie, they seemed so natural. It scared me a little.
After that song, the four of us stayed on the dancefloor, talking and introducing ourselves. My partner said his name was Tom but with the noise of the place, I didn’t catch the other one’s name. Tom took my hand and kissed it. That was a little strange but it made me feel pretty … feminine … nervous. I was afraid of what I might let this man do!
Anna gave her partner to Becky feigning sore feet. The next number was a slow one, so our partners moved in close with us. When Tom pulled me in close, my heart was beating fast—I could feel it about to burst from my chest! I thought he might be able to hear it! Tom painted my face with his eyes and I held my breath in momentary panic thinking that he might discover my secret. Then he slowly smiled, and still looking into my face said,
“Jill, you are a very pretty girl! But, you probably hear that all the time!”
“Well, no girl ever hears that often enough, but thank you Tom!” I said in a soft sweet feminine voice.
His smile told me that he was buying my feminine voice and manner. As he looked into my eyes, his lips were so close I almost reached out and kissed him, I so wanted to see what that was like, but I controlled the urge. He said,
“You have a very nice voice … very feminine!”
“Well, I am a soprano for a local church chorus (I lied, I’m a tenor), I love to sing!”
“Uh oh, a nice church girl huh?”
“Mmm, not always so nice I guess.” I said to him with as coy a smile as I could manage.
We continued dancing close, and his hand moved from my hip to the small of my back. This had the effect of pressing his groin against mine. Dressed as a girl—as Jill, I felt a tingle at having a strong man’s hands on me. I wanted him to touch me. After a minute or so, his hand accidentally slipped onto the seat of my tight shorts. He corrected it immediately saying,
“Oh Jill, I’m so sorry I didn’t mean to…” I interrupted him,
“It’s okay Tom honey! It felt nice!”
I replaced his hand directly on my ass. His large strong hand felt amazing on my little ass as he gave me a gentle squeeze! Then he put a finger under my chin, lifted my face, and kissed me. I felt a shiver running through my entire body as his strong lips pushed into mine. God! It felt so good to kiss this man.
Hello? Jamie? Are you in there somewhere? I tried to think to myself, but, there was no answer of course, so little Jill was now on her own. Give him something, but not too much! the ‘Jill’ in me was thinking.
As Jill, it was thrilling but as Jamie, I would never have conceived of letting a man kiss me! He pulled me in closer and I laid my head on his chest. He took full advantage by softly rubbing my behind, and even slid a couple of finger down the seam of my shorts between my ass cheeks. It felt so good I let out a sigh to let him know I liked it.
I moved my face up to his, parted my ruby-painted lips and kissed Tom softly but ardently. I loved it! God, I loved kissing by this man, I was loving being a girl! I was beginning to think that if Tom, wanted me, I would let him do that too. But, I had my sweet Anna to think about, and the ‘Jamie’ in me would never even consider such a thing.