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Jimmy to Jamie
This is my first attempt in this category. It was an idea that just grew over a small bit of time. Hopefully it will entertain you readers.
As usual, all characters engaging in sexual conduct are over 18. This is a fantasy, please read it as such.
This story employs themes of androgyny, gender fluidity, and MTF transgenderism. If these themes aren’t ones you like, please find other works to read as there are many, many very good works available to interest you.
Finally, please rate and comment on the stories you read. It is the only way authors know what to write the next time.
The Early Stages
I’ve always been interested in women, but not in the usual ways boys are interested. I’ve been interested in how they look, what they wear, their makeup, their hair, and their feminine ways.
At the earliest age, I can remember my mom hugging me to her and stroking my thick, honey blonde hair, telling me that girls would kill to have hair like mine. I smiled as she told me this. It made me feel good inside.
As I grew older, my mom was the one who raised me and impressed values on me. We took care of each other and looked out for each other.
My father was only but a sperm donor. As soon as he found out Mom was pregnant with me, he left, but he provided for us. He told Mom he just couldn’t be responsible for — tied down to – a child and a wife on a daily basis.
He was well off, so he set up funds that addressed our needs and many of our wants. We had a house with a yard, a car, clothing, and food. About all the responsibility he wanted was to write the occasional check to support Mom and I.
As a teenage boy, I was not physically large or impressive. My looks were average; my face had a softness to it, oval-shaped, clear pale skin, with high cheekbones, a narrow nose, and full, but not overly full lips. My eyes were piercing blue, and I had my hair, my thick, honey blonde locks that I let grow long. I was lithe and fit, just by nature. I didn’t work out.
I didn’t have many friends, but I also wasn’t a loner. I wasn’t part of any of the usual cliques — jocks, freak, popular, cool. It was me and a few other guys, all of whom were quite unremarkable.
As with my looks, I was an average student. Mom would chide me about improving my grades, and I tried, but never succeeded. She’d give me encouragement, and of course she gave me loving hugs.
One day after school, we had our usual conversation and afterwards she hugged me tightly to her. And she said something she’d never said before.
“Oh, Jimmy, you are such a beautiful person, and you have such gorgeous hair. If you’d been my daughter, we’d have had such a different experience together.”
Now, my Mom is a petite lady, she’s only about 5’2″, but she is beautifully proportioned with lovely curves; hips that are wonderful, and ass this is taut and beautifully shaped. But her boobs! Her boobs are, in a word, huge. So huge that had to check her bra size when doing laundry. She is a 32 EE cup. So, she is the desire of every man, and every young man that looks her way, including this young man.
So, when she hugged me that day, and said that to me that day, I became aroused. I could not help it. I’m an 18-year-old teenage male with hormones running out of control. She squeezed me to her breasts, mashing them against me, and pushed my ass toward her crotch, causing me to get hard.
I know she felt it because she squeezed me harder to her as I became more erect. She held me and whispered in my ear, “If you were my daughter, this hug wouldn’t be so embarrassing for you with your hard cock pressing against me.”
I was stunned! I said, “Well, Mom, I’m your son, and you hugging me like this has that effect on me, and I can’t help it.”
She cooed to me, “Oh, Jimmy, I know, I’m not disappointed. It makes me happy that you feel that way about your old mama.”
“Mom, you’re not old, and I love you. But I’m 18 and nearly any physical contact with a woman gets me aroused.
She smiled and said, “I know honey, and all I’m saying is that if you were my daughter, we’d just smell each other’s musk as we got wet.”
After that, I’m thinking to myself, ‘holy shit, she’s turned on too!’
We finally separated, but my hard cock was still visible in my pants.
Mom said, “Sorry, honey, I didn’t mean to get you so excited. It’s different with girls, and not so visible. Please forgive me.”
I approached her and kissed her and said, “Don’t worry about it, Mom. I’m fine.”
But in reality, her comments about if I was her daughter, vice her son, began to make me think about things.
I wasn’t very masculine per se, I was very thin and lithe. I had little to no body hair, even around my cock and balls. I had what many might call feminine features given my face and long, thick hair. I began to think that maybe I was more androgynous than I knew, and Mom saw that.
Time passed and I eventually wound up attending a community college in the fall after high school graduation. But I was still questioning my görükle escort sexuality. I let my hair grow long, down to the middle of my back. I began to dress in loose-fitting tops and tight-fitting jeans. The tight jeans showed off my ass and thighs that screamed femininity.
I experimented with very light bits of makeup; eye liner and some transparent pink lipstick to give my already full lips a bit of pop. My blue eyes were much more attractive with the eye liner.
The effect at school was that I had both guys and girls hitting on me, which I found oddly erotic. I liked and was attracted to women, but the idea that young guys found me attractive enough to hit on me was a complete turn-on. I never led them on, but from an ego perspective, my confidence was off the charts.
One afternoon, a goth-looking girl approached me and asked if I’d like to get a cup of coffee with her. I immediately agreed and we found the nearest Starbucks.
She introduced herself as Lydia, and I introduced myself as Jimmy. We talked about school stuff for a while and then she asked me, “Jimmy, are you interested in girls, guys, or what?”
I was taken aback by the question, but then realized that I presented very androgynous, so I told her, “I’m interested in you, right now. I’m a guy and I see you as a girl, and would like to see more of you.”
Lydia smiled and said, “OK, let’s date for a bit and see where it goes.”
I smiled back and said, “That would be great!” We exchanged numbers and then, over the next few weeks, dated several times. We had lunch, dinner, went to movies and concerts, and generally enjoyed each other’s company immensely.
After about a month, I invited Lydia back to my place for the evening after we had a casual dinner out. We walked hand-in-hand back to my apartment and when I opened the door, she pushed me in, closed the door behind her and grabbed me to her, kissing me deeply.
I returned her passion probably tenfold, squeezing her, groping her, and forcing my tongue deep into her mouth. We moaned and kissed and groped and then finally fell onto my couch.
Lydia stripped off her clothing faster than I could imagine possible, and then she stripped off my clothes just as quickly.
We were both highly aroused. I was rock hard; she was dripping wet. While I was not blessed with a monster cock, I was a pretty thick six inches when erect.
Lydia got on top of me and slowly impaled herself on my stout six inches. She moaned, as did I, and then rode me for what I was worth. I was not terribly experienced, but Lydia was indeed much more knowledgeable, riding me expertly.
She was able to keep me from coming immediately, while getting herself much closer to orgasm. She worked me hard, and then finally said, “I’m close, I want you to come inside me. Can you do that?”
Are you kidding me? “Yes, baby, I can do that. Keep riding and I’ll fill you up in a few more strokes.”
She smiled and clenched her pussy around my cock. “Come with me!” she hissed.
I needed no additional instruction. My body tensed and I felt my seed shooting out the tip of my hard cock deep inside Lydia’s pussy.
Lydia felt my orgasm and it clearly tripped her to come. She clamped her pussy around my cock and began to buck wildly, yelping and shrieking along the way.
I grunted as the last of my seed pumped inside Lydia’s sheath.
She fell on me, gasping and kissing my cheeks and neck. “That was wonderful!”
I concurred and we nodded off in each other’s arms for a while.
Lydia awakened first, but I was not far behind her. She began to talk to me.
“Jimmy, I have to ask you. You are a great lover, but you present very Andro, if not femme. Are you bisexual?”
I thought for a bit and said, “To be honest, Lydia, I’m not sure. I really enjoyed making love to you tonight, but I have these thoughts running around my head about being a girl. I know that doesn’t make sense, but that’s the truth.”
Lydia asked, “Have you ever been with a guy?” It was an honest question, not judgmental or condescending.
“No, I haven’t. But I’m not sure that it’s out of the question.”
Lydia pondered that and said, “That’s really interesting, and to be honest, a real turn-on for me.”
I smiled and said, “Well, I aim to please.”
She laughed and slapped my chest.
Lydia dove deeper into my androgyny. “Jimmy, I love how you look. You could be a girl or a boy. You have soft features, beautiful long hair, great eyes and lips. You have a body that straddles the line as far as being male or female, well, except for your cock, but with very little effort, you could pass as either male or female convincingly.”
I stared up at her, lovingly and asked, “Well, what would you prefer?” I had opened the can of worms and was unsure how I’d deal with the outcome.
Lydia smiled broadly and then a little lewdly. “I don’t quite know. So, how about we try both?”
I immediately became erect. “You want me to be a girl and a boy with you? Are you bisexual?”
She smiled bursa eskort again and said, “Yes to both.”
I was a little dumbfounded. The girl I had just made very passionate love to was now saying it would be ok if I expressed my gender-fluid self with her in both roles, male and female.
“So, if I were to present femme to you, how would an evening like tonight go?” I asked with genuine curiosity.
Lydia thought for a few minutes and then said, “I don’t really know. I’ve never explored that side of my sexuality, but I think that I’d really enjoy doing that with you. Are you game?”
I didn’t think very long before I said, “Of course!” with a big smile on my face.
We proceeded to make love again for a couple of hours and then fell asleep.
We woke up together in the morning, hugging and kissing. It was Saturday, no school to worry about. I got up to make some coffee while Lydia laid in bed, completely naked, waiting for me to return.
I came back with coffee and we laid there together, silently sipping our steaming morning brew.
Lydia then spoke up, “OK I want to plan an evening with you, both of us en femme, so that we will be seen as a lesbian couple when out and about. What are your thoughts?”
Admittedly, I was intrigued, and my hard cock betrayed those thoughts. My simple response was, “I’d love that. Let’s figure out what I need to do to make it work and do it.”
Lydia was overjoyed.
Lydia went into girls-night-out planning mode. “OK, we need to get you some lingerie, stockings, heels, a skirt or dress, and then a spa session.”
I was happy to agree and begin this process.
We cleaned up and after a little more sex, got dressed and headed out.
Lydia took the time to do my hair in a more feminine style, and put a light amount of makeup on my face to accentuate my already feminine features. She tied my hair back in a loose pony tail and I was set. I looked like a tomboy-ish girl, and was happy about it.
“There’s two things, though.” she said.
“What?” I asked with curiosity.
“Well, you need a girl name, so how about Jamie?”
I thought for a few moments and said, “Sure, that’s perfect.”
“And, there’s you bulge.”
I looked down and my cock and balls were very prominent in my shorts.
“What do we do?” I asked naively.
Lydia said, “Simple. We tuck you and tape you.”
“OK, what’s that?” I again asked naively.
Lydia smiled and said, “It’ll be easier if I just show you.” and ran off to the bathroom, returning in a second with some bandaging tape.
She said, “Drop your shorts and undies.”
I did as she instructed. She noted I had taken a pair of her panties this morning.
“Such a naughty boy, taking my dirty panties to wear!” she smirked.
I smiled and said, “Well, we’re going to shop for girl clothes. I can’t be wearing boxers.”
We both giggled.
Lydia began the process and explained what she was doing. “OK, so your balls have a little home up there in your body and I’m going to push them back up in there. It might be a little uncomfortable at first, but don’t worry.”
I nodded. I was enjoying her manipulating my balls.
She continued, “Now, I’m going to pull your cock back between your legs and tape it so it doesn’t show. This means you’ll need to sit when you need to pee.”
I nodded and let her do her magic. Again, I was enjoying her playing with my cock.
A couple of minutes later she was done. “Pull up your panties, Jamie.” she instructed as she went to put the tape back in the bathroom.
I liked the way that sounded and I did. I was completely flat up front and everything felt strangely comfortable as I walked around.
Lydia returned and took a look at her handiwork.
“Look at you! Perfect! You could wear yoga shorts and nobody would know!”
Again, that thought excited me. I said, “OK, Jamie is ready for her shopping spree!”
We both giggled again like teenaged girls. My voice wasn’t masculine at all, so I didn’t really need to worry too much. Lydia just warned me to speak in quiet tones and nobody would be the any the wiser.
Our first stop was Victoria’s Secret, where we looked at, picked out, and I tried on a whole bunch of lingerie. I was only slightly self-conscious about using the changing rooms, but with Lydia’s encouragement, it was not a problem.
I tried on all the panties we had picked out and came away with five pair that we both liked. The bras were a little bit more of a challenge, as I had no boobs. Lisa told me to stay in the fitting room and left.
Within fifteen minutes, Lydia had returned with some breast forms with adhesive for me to use for the bra fitting.
She carefully and lovingly attached the breast forms to my chest, making sure they looked proper and balanced.
I proceeded to try on the bras and came away with five that met our collective likes.
We paid for the goods and then proceeded to trendy store that catered to young women. Lydia browsed the racks, pulling items she wanted bursa escort me to try on.
We went back to fitting room and, astonishingly, everything Lydia had selected was perfect. I looked like a hot young club-going babe looking to get laid. I was thrilled.
We paid and left the store, heading back to my apartment.
I asked, “What’s next?”
Lydia said, “We have two more stops. I need you to be brave on this first one.”
Not knowing what she was talking about, I simply said, “OK, whatever you want, babe.”
Lydia smiled and pulled into a women’s’ costume jewelry store.
We got out and I followed her in.
“Go sit in one of the chairs.” She told me. I complied.
Lydia came back with a few sets of earrings and studs, and a girl with what looked like a gun in her hand.
Lydia said, “OK Jamie, this is Crystal. She’s going to pierce your ears and your bellybutton.”
My eyes got large, but Lydia calmed me. “Go with it, you’d feel great afterwards.”
I acquiesced and got my ears pierced twice each, and got a bellybutton piercing. Lydia was right, I felt great.
As we were heading home, we saw a nail salon up ahead. Lydia stopped and said, “OK, last stop. We going to get our nails and hair done.”
I didn’t argue. In for a penny, in for a pound.
Lydia introduced us to the girls in the shop and told them we needed to get dolled up for this evening.
The girls buzzed around us, doing giving us a manicure and pedicure making us feel pampered.
“What color?” the girl asked me.
Lydia chimed in and said, “Oh, she needs bright red!”
I smiled and nodded, “Bright red it is!”
My fingernails and toenails were painted, and I have to say they looked beautiful.
For our hair, they just gave us both a quick blowout and added a slight curl to the end of my long locks.
The girl working on my hair said, “Oh, Jamie, you have such gorgeous hair! I’d kill to have hair like this.”
Turns out Mom was right.
Finally, we got home and unloaded our haul. Actually, my haul. It was my new femme wardrobe and we were going to get ready to go out to dinner and a club afterwards.
Lydia instructed, “OK, strip off your clothes and get into the bathtub. I’m going to shave you all over from the neck down.”
It sounded kind of exciting. Lydia got started and lovingly shaved me all over. But first, she had to untape my tuck, which she did with great care.
She used hair remover on my chest and legs to make it easier, but she took great care in shaving my cock and balls until they were smooth like a baby’s bottom.
I felt so sexy being bald all over!
After shaving me, Lydia moisturized me all over with a lovely lotion that made me feel like a complete woman. I was sure that being treated like a woman would turn me into the best woman I could be.
Lydia laid out my clothes on the bed right next to hers. We were going to be a couple of very hot women tonight at dinner and afterwards.
“OK, before you get dressed, we need to take care of something again.”
Lydia approached me a kneeled down so she was looking at my cock and balls.
She went to work, pushing my balls up inside me again and pulling my cock back and taping it.
“This way, you can go to the ladies’ room and pee sitting down like the rest of us girls.”
I laughed a bit and said, “OK, sounds good to me! But, when I have to go, I want you to come with me, at least the first time.”
Lydia laughed and said, “Oh Jamie, girls always go to the bathroom together. All the time!”
I giggled like a little girl, and it surprised me. This whole process had kicked off something in my head and opened a gateway to my feminine side. I was feeling feminine from the inside out, and it felt amazing.
“OK, dreamy girl, time to get dolled up.” Lydia’s command broke me from my reverie.
I put on my black high cut bikini panties that had mesh cutouts on both hips. Lydia carefully attached my breast forms and then helped me with makeup to blend them into my chest. When she was done, I could not tell that my breasts weren’t real.
“Perfect!” Lydia whispered to me. “You look so feminine, and we are just getting started!”
I smiled and then slipped on the matching demi cup bra, adjusting my “boobs” so that I had cleavage. I could see Lydia salivating out of the corner of my eye.
Next was the underbust corset with matching garter. Lydia helped me close the corset to give me a gorgeous hourglass figure. I had to learn how to breathe with it laced tightly around me, but it was worth it.
Lydia instructed, “Panties off. They go over the garter so when you need to pee, it’s not an all-night project.”
I slid off my panties and then rolled my thigh-high stockings up each leg and attached the garter straps, with a little guidance from Lydia.
Then, a black pleated skater skirt and a sheer red top that showed off my bra and corset.
Lydia gasped as she took me in. “My god, Jamie, you are so sexy in that fit!” She came over and kissed me passionately.
Her soft lips met mine and I immediately melted into her. I felt so feminine, and her kiss made me feel even more so. I was getting aroused, but not in my usual way. With my cock taped back, it couldn’t get too very hard, but I felt my panties get wet as precum leaked from me.
Ben Esra telefonda seni bosaltmami ister misin?
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