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To the readers: This story has become a longer saga than I ever intended it to be when I first conceived it. In this penultimate chapter, Jamie finds that his (and his alter ego Jill’s) new-found freedom to date around after breaking up the Anna, is coming at a cost.
Thank you all for sticking with this story. The next chapter, Chapter Four, will offer some twists, and bring this story to its conclusion. Thank you, M142
Part Eight: Jill and Diana.
Janet and I were very professional at work, cordial but not any more than that. She mostly stayed at her desk, and only came into my office when absolutely necessary. Janet started to wear simpler and less revealing clothes, trying (successfully) to hide her natural assets from my eyes. All of my tries to engage her in conversation ended in her changing the subject back to our work.
So, we did our jobs, and went our separate ways after work. I was so worried that in gaining some amount of freedom, I lost Janet. I started to have doubts about wanting all that freedom … if it was becoming freedom from her! I had lunch with Becca on Tuesday, and we discussed our promise to get together Friday night.
Anna called me at work and asked if she could come over Tuesday night. I agreed. She was there promptly, and we decided to have a night in, and we made dinner for ourselves. She was sweet and loving—just as I remember my high school triumvirate friend being.
We talked about Becky, and Anna told me that she was doing fine, and actually had a boyfriend she sees regularly and likes. I made a mental note to call my old friend and wish her well with her new friend. We talked about our lives, and Jill’s experience with Tom. I mentioned to her that I was thinking about putting Jill in mothballs for a while until I can re-examine being with another man. She thought that was a healthy thing to do.
She said that she was not dating anyone currently, but concentrating her energies on work, and hanging with Becky when she was not out with her new boyfriend.
We were having a pleasant evening together. After dinner we listened to music, and even danced to a couple of tunes. It felt so good to have her in her arms again. It started to get late, and she said,
“Well, Jamie! I should get going!” Anna said.
I quickly and earnestly, said, “Anna! Stay!”
She looked at me, smiled, walked over to me, and kissed me, as she said,
“Alright Jamie! But I have to warn you, I don’t like condoms … are you okay with that?”
I told her that I was, and she took my hand and led me up to my bedroom. I had forgotten how truly lovely Anna was, as she slowly undressed, teasing me a little, but I was enjoying the show as she stripped right down to nothing. She stood in front of me rubbing her breasts, and let one hand slide down her body massage her stomach and then her mound.
She slid into the bed, giving me a prolonged view of her exquisite little ass with its private little pucker winking back at me. Anna has the most beautiful little ass of all my girls—even Kim!
She turned onto her back and let her hand slide down her body again and plunged two fingers onto her pussy as she spread her legs. She pulled her fingers out, and they were very wet! I quickly stripped, and slid in on top of her, between her legs. I just slid into her little pussy, and built from insertion, to slow strokes, to quickly taking her hard.
“Anna, you feel so good to me, honey!” I moaned as we moved in a perfect rhythm together—her pushing up against my thrusts, and as she whispered, “Jamie, I have so missed your touch, your feel inside me!”
We both came fairly quickly, and just held each other through our mutual shudders and moans. It felt so good just to relax and let myself release inside her. We just laid in each other’s arms for a long time without saying a word. She broke the silence asking me if I still loved her. I told her that is was an unfair question, but I would always have her in my heart.
We made love twice more before morning. I made her breakfast, and we parted ways after pushing our mouths together in a perfectly symmetrical kiss, and her whispered request that I call her sometime, to which I agreed.
~ ~ ~
Waiting for Becca, I picked up my phone and called Janet. Her phone rang and rang until it went to message. I wasn’t sure what I wanted to say to her but ended up with,
“Hi Jan, it’s me … Jamie. I miss you! Call me sometime and I’ll make dinner for you! (pause) Okay, bye!”
She should normally be home, or at least have her phone with her, so I was guessing that she was screening her calls just now—screening me out! She seemed to be supportive of my gaining my freedom, but somewhere along the way, and for a reason I can’t even guess at, she changed her mind. She might have a giant IQ, but she still had a young girl’s fickle heart.
I miss her! I see her at work, but she doesn’t smile at me. She won’t let me in!
Becca was over early on Friday, and after dinner together, she Bayan Eskort helped me get Jill ready. That’s something she really loves doing, and she does it with lots of kisses and touches as she works on me. She straddled my while I was still undressed, but prettily made up, and placed little kisses all over my pretty girl’s face, and tasting my soft, pouty and reddened lips.
“Ohhh, Jill!” she moaned, as our hand explored each other’s soft feminine bodies.
She still had a glow from our intense love making at our last meeting, and she gave me a nice blowjob before tucking me under. We stood, looking into each other’s eyes, and then she fluttered them closed and gave me a ‘cummy’ kiss.
We were finished, and both stood in front of my full-length mirror, arms around each other, looking over the latest iteration of my transmogrification from Jamie to Jill.
“Jill honey! I can never get used to the transformation, my pretty boy becomes a beautiful girl! You are going to break hearts tonight honey, just make sure mine is not one of them!”
I turned her toward me with my hands on her lovely shoulders, and said,
“Becca, you know that I need to explore Jill’s potential right now, and I don’t want any borders imposed on her. Can you bear with me for a while?”
She lowered her head and grudgingly said, “I guess so.”
“That’s my girl!” I said and kissed her on top of her head. She raised her head and asked,
“Am I Jamie? Am I your girl?” I just smiled, kissed her on the cheek, and said,
“C’mon, let’s go!”
The club was crowded, but it was Friday night. Becca and I both got our asses squeezed and pinched as we made our way to a table near the dance floor. We ordered a drink, and I left enough for it and a tip on the table, grabbed Becca’s hand and we were dancing to a very lively number and having fun. As I looked over her shoulder, I saw a pretty dark-haired girl who couldn’t seem to take her eyes off of Becca and me, as we danced. She smiled when I looked over at her.
Afterward, we returned for our drinks already at the table. We were talking and laughing for a while, and then we heard a familiar voice,
“Wow! The two prettiest girls in the club!”
It was Tom, he asked me if I minded, and took Becca’s hand to lead her out onto the dancefloor. It was a slow dance and Tom pulled her in close. I was happy to see her having fun, since I do not really have any hold on Becca. A handsome man approached me and asked for a dance, and I politely declined.
Watching Tom and Becca dance, I was reflecting on Tom’s change of attitude toward me after making love to Jill. I know that he loved that, but he seems to be showing interest in all of my girls, likely in retaliation. Retaliation for Jill’s bringing something out in him that he seemed uncomfortable with. He loves women, of course, but he loved Jill as well, and I got the feeling that he is punishing both Jill and Jamie for exposing that side of him.
Just drinking my drink, and watching them dance, my mixed thoughts were interrupted by the little girl I noticed earlier, plopping down at my table. She smiled,
“You don’t mind if I join you, do you, sweetie?”
“Of course, no! My name is Jill!” she took my offered hand, and shook it by the fingers.
“I’m Diana! Let’s dance Jill!” she said cheerily.
She was very pretty, and very feminine, with soft, well-defined curves. I was thinking that she might be someone who might interest Jamie. We rose and moved to the dance floor and I put my hands her hips, and she put hers on my shoulders. I looked into a pair of exquisitely lovely dark eyes, expertly made-up. She was wearing an extremely short black dress, and four-inch spike heels.
She was so slender that although her dress was very tight and very short, she didn’t expose much; only her long slender legs, nearly all the way up! Her dress had no back to it, and the front provided a hint of small, but firm breasts. I was in a more modest dress, but did show some cleavage and without a bra, I relied on my growing little natural breasts from my hormone treatments. They were just small mounds, actually!
Diana reached up and kissed me sweetly on the lips, and with a smile, asked,
“What’s your name, honey?”
“I thought I introduced myself, I’m Jill!”
“Yes, I know. What is you real name?”
I gave her kind of a confused look, and then she surprised the hell out of me by saying,
“Mine is David!” She smiled, just waiting to let that sink in.
“Well David, you are a very pretty girl!” Was my response, still quite surprised. She blushed and said,
“Let’s get some fresh air so we can talk.”
We walked out the front hand in hand, and as she passed the bouncers at the door, she smiled at them and I watched as they had their eyes glued to her ass as she passed, I am sure they noticed mine too. We found a quiet spot, and I noticed a pair of black silk panties as she perched on a low wall.
“You are very pretty, Jill, Anadolu Yakası Escort but I can tell the difference … you know?” then she laughed. “I’m sorry darling, but you look so confused!”
Then I answered her question, “My name is Jamie, uh James.”
She relaxed into a nice smile and again offering her small hand, said, “Nice to meet you Jamie!”
I asked, “So how long have you been doing this Diana?”
“A long time, Jamie. I am in the process of changing. I am going to have the operation in about six months or so. Jill. I am a girl inside, and as you might know, I was beaten up a lot in high school. What about you?”
“I am a heterosexual—I like girls. In fact, I just broke up with a long-time girlfriend. She and another female friend dressed me up like this to go clubbing with them, and I kind of liked it. I have had hormone treatments, but just to get away from having to use breast forms when I am Jill. If I quit doing this, I will likely stop the treatments.”
She looked me up and down and said in a soft voice, “We are all alone, Jill. You can touch me!”
I moved in and put my hands on her legs and then slid them up her inner thighs as she opened her legs for me. Her hips were level of mine as she sat on the wall. We moved into a soft kiss, that grew in ardor. She was a dream to kiss, and our lips melted together, and I felt her tongue slide past my lips. My hand slid up over her hips, inside her panties and onto her soft, silky ass.
After several minutes, we pulled back from our kiss with my hands still on her. She slid her hands inside my dress and onto my breasts. She squeezed and fondled them, and pinched my nipples. The treatments had given me puffy areolas, and larger nipples, which have become increasingly sensitive to touch.
“Jill, they are lovely! But treatments only go so far, you need implants you know. Here feel mine.”
She pulled her dress off one shoulder exposing one very pretty round breast. I put a hand to it and started to squeeze. It felt so good, and I couldn’t tell that she had implants. I was impressed that she didn’t get carried away, but decided on smaller implants that best fit her shape.
“Diana, you are a very beautiful girl. I might … like to see you again.”
“Well, we have tonight, darling, so let’s start there! She said with a musical little laugh.
Back at the table, the waitress had just left a new tab and a pen on the table for our drinks, Diana tore off the bottom of the bill, and wrote her name and number on it. She handed it to me, and said,
“Tuesdays and Thursdays are good for me usually; I would love for Jamie to take me out to dinner. But for tonight, I don’t want Jill to escape, can you arrange it?
“Wait here.” I stood just as Becca and Tom were returning to the table. I introduced them to Diana, and grabbed Tom’s hand for a dance, leaving Becca with my new friend.
“Jill! You look very nice tonight!” Tom said, “But you have me confused after our date, we will have to talk about that!”
“Tom, that’s nice of you to say, and we will talk about it sometime.” Then I changed the subject, “But Tom, I have met a new friend that I want to spend some time with tonight. Can you take Becca home? Tell her I will make it up to her!”
“Alright, Jill. I’ll get her out on the floor for the next one, and you can leave. I’ll talk to her. Are you sure you trust me with her?
I wasn’t really sure, but I wanted to be with Diana, so I said,
“Yes, Tom. You are a good man, and I know Becca likes you. She can do as she wishes.”
Tom had been holding me off a little, but was compelled to give me a little kiss. We returned to the table and I signed the tab, paying for our drinks, and Tom asked Becca out on the floor. When he pulled her into an area out of sight of our table, I turned to Diana and said,
“That’s our cue! Your place or mine?”
“Mine. I’ll give you directions.”
We left quietly, but both had our butts squeezed once or twice on the way out, pushing our way through the crowd. Outside, she said,
“Some asshole got his hand inside my dress and on my boob!”
I laughed and offered, “I know, right? I have a full collection of bruises from being pinchedt.”
She laughed, and said, “You can show me yours, and I’ll show you mine!” We both laughed heartily. Then she kissed me, and said,
“See you at my place, Jill!”
~ ~ ~
Diana had a very upscale apartment in a posh high rise near downtown. It was furnished in extremely good taste; she told me that the couch was covered in Italian silk, imported from Milan. She had a nice wine cooler, which held about two dozen bottles. She selected one—a dark red—and paired it with and assortment of cheeses, some grapes and strawberries.
We were sitting on her lovely couch, with its subtle silk striping, and I said,
“Tell me about yourself, Diana.”
She launched into her story:
“I realized that there was some confusion between my plumbing Pendik Escort and my mindset, at the age of about eleven. I was interested in boys, but I didn’t think of myself as gay. I was beaten up many times and called, ‘queer,’ ‘homo,’ ‘sissy boy,’ and the coup de grâce, ‘faggot’! I talked to my parents about it finally, when I was eighteen, and they were very understanding.” (sipping her wine)
“They helped me find a specialist for some counseling, and eventually to explore a change. It was a long process, and now, at twenty-seven, I am close to that goal. Jill, I want to be with you tonight, even if we just hold each other.” (another sip) “So, cutie, what’s your story?”
I thought about what I might say, and then started in,
“Diana, I am a hetero as I have said, and although I am not really effeminate I was always a pretty boy, and I did get teased. I was a shortstop on our high school baseball team, and I was liked and protected by my teammates, so I never saw my locker from the inside with the door closed. I still see my friends from time to time.”
I took a sip, and as I looked into her lovely eyes, my heart skipped a beat. Then I continued,
“Some time ago, I expressed some concern over what my girlfriend Anna, and her best friend Becky did on their girl’s nights out. These two little monsters decided to take me out clubbing with them … dressed as a girl. So they bought me a lot of girl-stuff, and made me up. One of the first men I met was Tom whom you met at the club Tonight, and we have gotten together both as Jamie and as Jill. He is very strongly hetero, but right now, he is confused about his feelings for me.”
“Well, that’s quite a story, Jill! Um, why don’t we bring this bottle into the bedroom!”
Her large bedroom was more richly appointed than the typical woman’s boudoir, with a king-sized bed covered with expensive satins and silks. It had French doors that opened onto a balcony. I noticed a large en suite bathroom with what looked like gold faucets.
She turned and pulled me into a kiss. Then she said,
“We are going to spend some time tonight exploring each other, darling. Both as Jill and Diana, and as Jamie and David.”
I was nervous! This person was so exquisitely beautiful that I needed to be with her. I had to do this! We slowly undressed each other down to our panties and stockings, since neither of us was wearing a bra. She took my hand and led me onto her bed, and we lay together in a close embrace. Her tiny frame seemed to disappear in her huge bed!
We kissed … a little, talked softly together … a little, and let our hands explore the other’s bodies … a little. She removed my panties, and I removed hers. We slid our hands over each other’s private area. Her skin was silky smooth, and she told me that mine was too.
I turned over her in reverse position and slid down her body. As I got close to her crotch, she voluntarily untucked her stuff, and I took her small slender cock in my hand. She became erect almost immediately, and hers was about my size, or maybe a little smaller, but slenderer than mine. She was completely shaven down there like I was, and her stuff felt very nice … silky.
With my cock positioned over her face, after I turned, I moved in just to smell her, and to taste her down there all the way down to the bottoms of her ass cheeks. Her aromas were intoxicating! Then I put her cock in my mouth, and started to suck her as I played with her tiny balls. She did the same to me. It felt wonderful having her soft lips around me, and also having her slender penis in my mouth.
I fondled her and sucked her with vigor, and she came before I did. She filled my mouth with her milky essence, and I licked her tiny cock clean, then moved my lips and tongue lower, between the bottoms of her buttocks, and I even teased her little puckered opening.
Her attentions to me caused me to stiffen and come in her mouth moaning and shuddering. I turned back around and with our cocks rubbing against each other, we kissed and fondled each other’s breasts for a long time. When we stopped, she got out of bed, and filled my wineglass. We sat on her bed, legs folded under us, in silence just sipping from our glasses.
She brought some of the cheese and grapes, and we took our time feeding them to each other. We laughed and giggled our pretty faces off, when feeding became throwing at. Then she looked into my eyes and said in a soft breathy voice,
“Jill, I want you inside me!”
I smiled, pushed another grape into her mouth, and helped her set the food and our wine glasses on the bedside table. I gently pushed her back, and asked, “Front or back?”
“Front darling, I want to look into your face. I want it to be less like gay sex, and more like boy-girl sex. Then she reached into the drawer for a condom, and a tube of lubricant. She set them on the bed next to her.
I reached over and took a grape off the table, put it between my lips, and pushed it into her mouth forcing a sweet kiss, as we both giggled like crazy fighting over possession of the grape. I let her have it. I moved my lips down her body, kissing and sucking her nipples into my mouth. I trailed my tongue and lips down to her stomach, and then to her cock and gonads, teasing them with my tongue.
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