Jamie's Story Ch. 03

I sat on my haunches, and pulled her hips up toward mine. She handed me the condom, and I rolled it onto my now very hard cock. I filled my finger with the lube, and slid it underneath her, and into her tiny puckered opening. She was so small! So tight!

I slid my finger slowly in and out of her, until she started moaning with her eyes closed, as she wrapped her legs around me. It felt so good to feel her fleshy insides with my fingers, and had a hard time stopping. But I did, and I adjusted my body, positioning my cock at her opening, and she opened her eyes and looked into mine,

"Be gentle, honey!" she said in a jittery whisper.

I pushed the tip of my cock into her and she gasped. Then I slid it in further, just an inch as a time, until my whole four inches were inside her. It felt amazing, so tight, so warm. I started stroking her in an easy rhythm, and then started pushing it in harder as she grunted and moaned with pleasure.

I leaned forward with my hands on the bed next to her for leverage as I slid harder into her and she wrapped her slender legs around me. She must have had at least two orgasms on her stomach and mine, before I stiffened, and came inside her. I lifted her body up, so she was straddling me with my cock still throbbing inside her.

I noticed that she had come on our bodies. She looked down at her stuff oozing down and put a delicate hand to her mouth softly giggling with a slight blush.

We kissed passionately, and I thought I was going to pass out from the pleasure of her lips on mine. She finally broke our kiss, and smiled, with her dark eyes glistening. With a blush on her cheek from out active coupling, she was beautiful!

"Jill, I loved being fucked by you, but I cannot reciprocate because of my developing orientation. If we still know each other in eight to ten months, I will have female equipment, and you can have me vaginally. In fact, I will let you be my first Jamie ... you may take my cherry if you wish!"

"Diana, I would love that!" We both laughed about that.

I laid her down beside her, and took her into a close embrace, and we kissed for nearly another hour. She got up, and I watched her pretty ass as she did. She pulled on a short purple robe. I had my overnight bag with me, so I used her shower, cleaned off all the makeup, and slipped into a pair of jeans.

"Come, my sweet man, let me make you something to eat."

She made us a couple of perfect omelets with coffee, and we just gabbed until I saw her yawn a little,

"It looks like you're tired, I should be running along."

"No, Jamie, please stay! Stay the night!" She pleaded.

Then she rose, took my hand and led my back to the bedroom, but we just cuddled, and kissed a little after I stripped my jeans, and we fell asleep in each other's arms. She felt so good in my arms; her soft tiny frame, and her intoxicating aromas filling my nose. I fell asleep with a smile on my face.

In the morning, she was up before me, exercising in just her panties and a sports bra. She saw that I was awake, and came over, leaned into the bed, opened her lips and pressed them into mine. As she did, her bra puckered open, and I could see a pretty little nipple. She looked down and then up at me,

"See something in there you like? She giggled.

"As a matter of fact, I do! You have very nice tits for a boy."

"Jamie darling, you're are a boy ... I am not!" she said with a laugh.

She crawled in to the bed with me, and let me make love to her once more, the same way as last night. I was glad to be able to take her once more. Then she rose, and headed for the shower. She came out in just a towel, and I took my turn again. When I came out, she was dressed in a skin-tight pair of blue jeans, a halter top, and white tennies.

I dressed in my customary jeans, knit shirt, and loafers with my long hair gathered at the back in a ponytail like some men with longer hair wear. She looked stunning, and I offered to take her out to brunch.

I selected a café I like, because it is frequented by some of my old friends from my baseball team. It is comfortable, and the food is good. Diana approved right away.

"Jamie, this is a nice place! Good choice honey, and if you are trying to impress a girl, well you have!"

We both ordered the heartiest breakfast on the menu, with coffee. I saw a couple of my old buddies at another table, and waved. They waved back, and one of them complemented me on my girlfriend pointing to her and giving me a thumbs up.

It was not long before a couple of men walked in I had never seen in this place before. They were loud, and borderline obnoxious, and then they crossed the border by bothering Diana, trying to hit on her. One of them told her that she deserved a real man, not this little wimp with a pony tail, referring to me. I politely asked them to leave us alone, but one sat down next to Diana, trying to get a kiss.

One of my friends, Jack, came over. He looked at the two and said, "Is there a problem here?"

"Mind your down business asshole!" The one sitting next Diana said without bothering to look at Jack.

Jack goes about six-four, and two-twenty. He picked this guy up out of the chair and pushed him away from the table. The guy took a swing at him, but Jack caught the guy's fist in his large hand. When the other guy started to move toward Jack to help his friend, my other two friends each clamped a hand on his shoulders, and one of them, Bob, said,

"Bad idea, dude."

When he tried to twist away, they tightened their grip on him. Jack had the first guy's arm twisted behind his back. My friends were having fun with these two guys, and just messed with them for a minute or two. Jack asked his prisoner to apologize to Diana,

"Fuck you, man!" He spit out at Jack. Then Jack tightened his grip until the guy winced and moaned with genuine pain.

"Want to change your so-called mind about that?" Jack asked.

"Alright, alright!" Jack let him go, and the guy said, "Sorry!" very curtly and insincerely.

Jack clamped his hand on the guy's shoulder so hard that he groaned in pain as he said, "Nah, I think you can do better than that."

The other guy tried to twist away again, he was stopped, and my friends put their arms around his shoulder like you would with a buddy, but holding him in place, and Bob said,

"You're good right where you are, pal!"

The first guy was made to sit next to Diana and give her a sincerer apology, forced to define his bad behavior, and his desire to reform. I think Jack had a lot to do with that script! But the man did deliver it, and the two of them left. Diana invited my friends to sit with us, and we had a great time. I noticed that she looked at Bob, and blushed a little. Bob is easy-going, but rather handsome.

Jack pulled me aside, and said, "Jamie, this one is a winner! Pretty, smart, and I like her. Hang on to her, dude."

We left after I agreed to a guy's night out with them sometime next week. I was looking forward to getting out with my friends again. Diana was impressed with my friends, and it made me feel good to be with her. She especially liked Bob, whom she said characterized as, "Cute!"

I thought briefly about a possible future with her, and what that might be like after the extreme procedures she is likely to have to endure over the next six to eight months!

We did talk about her predicament. Diana prefers not to be called David anymore, since she is setting her mind as well as her body to the task of sexual reassignment—to finally become what she was meant to be in the first place ... a woman with female sexual organs. She is a successful lawyer at a large law firm, and her employers are not only behind what she needs to do, but they made her a senior associate, with partnership potential.

I told her that whether or not we dated or became romantic, I would be there for her through her process. She asked me to spend one more night with her and I agreed. She let me make love to her twice—wearing condoms both time.

She was okay with mutual oral sex, and receiving anal sex for now, but not with giving anal to me or anyone. Being the aggressor that way is not feminine in her mind. I found that she was a very nice sexual partner, and we developed a deep affection and respect for one another.

Before I went back to Diana's with her, I called Becca to check on her availability. She said that she was spending the weekend with Tom, and they were going sailing tomorrow all day. She asked if she could spend a couple of nights with me during the week, and I agreed.

I was happy for both her and Tom, but had a weird feeling about it I couldn't account for.

Part Nine: Continuing my journey of discovery.

On Monday morning, I found Janet to be just a little nicer than she had been since she slammed the door to my town house a week or so earlier. I invited her out to dinner, and she accepted. I told her that I would pick her up at seven, and she wanted to drive to my place instead. I asked her to pack an overnight bag just in case. She said ... "maybe!"

I have never been to her apartment, but I know that she has an array of sophisticated computer equipment, and that she is working on a large project of her own. She can't let me help her, or to even know what it is, due to my association with our mutual employer.

She feels that my being there, and being her boss, might compromise her copyright. She never talks about it at work, since she can't, and I know she is working with a copyright lawyer. If, or when she completes her project, it could be worth millions!

She arrived in front of my place, and I offered her a space in my garage to park. She handed me the keys, and walked in after I parked it for her. I came in from the garage, and my pretty guest already had a glass of wine for each of us. We stood close as we raised our glasses. Then I took hers, set it on the counter, and did the same for mine. I took her face in my hands, and kissed her.

Her lips melted into mine and she moaned softly. She missed me as much as I missed her, but she was still fighting against showing it! She looked very pretty in a light blue dress, that was very modest, with low heels. I was intent on having just a nice romantic night with her tonight. Whether or not we ended up in bed was not important. I just wanted to be with her and enjoy her company.

I drove us to a favorite restaurant, smiled at my lovely date and said, "Janet, I am so happy you agreed to our date tonight!"

"Are you really, Jamie? That's sweet!" then in an afterthought, "Jamie, I know that I have been standoffish lately at the office, but I am trying not to have my heart broken ... I have strong feelings for you!"

"Are you staying overnight tonight?" I asked.

"Haven't decided yet."

"What if I get you drunk enough?" I teased. She laughed,

"You wouldn't do that Jamie; you are too nice a guy!"

"C'mon Janet, no guy likes to be called a 'nice guy'! It is usually the kiss of death from a girl!"

"Well, not from this girl! Nice is nice!" Then she changed the subject, "So, Mr. searcher, how's the search going? I have been such a shit to you in the office, that we haven't talked much."

"Well, mostly it has been Becca lately. I have another date next week with Anna, so not sure how that will go. I did meet another 'Jill', sort of the other night. Her name is Diana, and she is set for sexual reassignment surgery in about six months. We spent some time together, and I like her, but of course there is no future there. I was out with Becca at the time, and gave her to Tom who was also there."

"Mmm, you can give me to Tom anytime you wish, honey. Tom is a hunk, and he's very charming!"

"Really? Really Janet?" I said in exasperation since she was with me on a date! She laughed and said,

"Yes, really! Give him my number!"

I couldn't tell if she was kidding or not, but I called her bluff by taking out my phone just to see if she would stop me. I started to text Janet's number to Tom's phone, saying that she wants to see him. I expected her to stop me, but she was not bluffing. It hurt me, but I did it.

It is beginning to look like I may have to find a whole new stable of women to be with since this well was sort of running dry. Tom as taking all of my girls! That pissed me off a little ... can't he get a girl on his own? Does he really need all my cast-offs?

She smiled when I texted her number to Tom, and just said, "Thanks, boss!" Her calling me boss was her way of de-personalizing our entire evening out. It felt like a punch in my gut from her. Our nascent romantic evening was not looking very good!

We did manage to have a nice time at dinner, and I decided to drive her to the park, for a little fresh air. We parked, and took to the walking path around the lake. We were just a little way down the path, and she got a text on her phone. I could tell it was from Tom, asking if she really wanted to go out.

She texted back, "Yes, Tom, how about next Friday night at seven. (then she included her address)"

A moment later, she received another text. From what I could see (she wasn't even trying to hiding it from me) it said, "Friday is good honey ... see you then ... wear something sexy!"

The she quickly texted back, "I will! Looking forward to it, handsome!"

She couldn't have hurt me more if she had hit me in the face with a two-by-four! I smiled wryly after she put her phone away, and I said,

"You, know Jan, it is a little breezy tonight, is it okay if we go back to my place."

"Well, I feel fine, but if you want to, we can!"

Her lack of feeling as she said that, made me wonder why the fuck I was even out with her tonight. We walked back to my car, and drove to my townhouse. Janet retrieved her overnight bag from her car, and I carried it upstairs, and put it in the guest bedroom. I opened a bottle of wine, and we settled on the couch.

We talked, and drank, mostly trying to connect in some meaningful way, but not succeeding. When it got late, Janet excused herself and settled in the guest bedroom, and I settled in my room.

In the morning she came down, and I had eggs going, so I made her a couple with buttered toast, and I poured her a cup of coffee.

Our relationship was not much better at work, but I could tell that she was itching to talk to me, and to hear about my life and activities. She crossed the line with me by asking for and accepting a date with Tom right in front of me, and as far as I was concerned, Tom did too. What was that prick up to?

I adopted a strictly employer-employee relationship with Janet, and after a while, I was not any friendlier with her than I would normally be with Casey, or Margaret ... or even pretty but shy Lindsay. In fact, I decided to give my pretty, if slightly full-bodied receptionist an ego boost, I took her out to lunch a couple of times. I was pleased to find out that she was quite smart, and poised, with a very good sense of humor.

Back at the car, my pretty but painfully shy receptionist grabbed my shirt and pulled me into her and kissed me. I could feel her amply beasts press into my chest. Lindsay gave me a very warm, and luscious kiss that had my lips tingling.

"Wow, Lin, what was that for?"

"Just for being nice to me, boss. You are a very sweet man and a good boss Jamie!"

I thanked her, and made a lunch date for next week again. I told her to wear something pretty.

~ ~ ~

Kim insisted that we dine at her place for our Friday night date, and she would cook something. I arrived at seven, and her place was filled with exotic aromas. She was dressed in a Japanese style dress that fit her slender form perfectly, and had a slit that went all the way up to her hip. It was dark blue with large flower designs running the length of her dress on one side. Her silky black hair was up in a smooth French knot, decorated with small white flowers. She was the very picture of elegance!

She brought me glass of California Pinot Noir, with a sweet smile. The table was set for several courses, and she after she seated me, she brought us a bowl of Miso soup, followed by an Oriental-style salad. Dinner was ginger pork, cut thin, and cooked with onions, and served with steamed rice. The food was perfectly cooked and tasted delicious, even for the palette of a gaijin like me.

Kim's conversation as intelligent, and topical as you might expect from a research librarian. She insisted on serving every item of the meal as is the Japanese tradition, right down to the homemade spring rolls, and finishing with mint ice cream.

After the meal we moved to the living room, and since she is someone who cleans up as she cooks and serves, the kitchen was spotless. I had to get my arms around this exotic beauty, and I put on some soft music. She smiled, and slipped easily into a close and comfortable dance pose. I was becoming hard just from my intimate contact with her, and she smiled a knowing smile, slid her hand down over me and said,

"Did I do that to you, darling?"

"Just happy to see you, Kim!"

Her laughter was muted and lady-like, with a musical element to it, with her small hand demurely covering her mouth. We talked as we danced, and with another glass of wine on her couch after the dance, she said,

"Jamie, there is a wonderful new movie out that I really would love to see, would you take me? Let's choose a late showing so we can have some privacy."

From her description, it sounded like a 'chick-flick' but I said,

"Sure, sounds nice, Kim!"

"Well, I will have to change, and I need your help to get out of this dress."

I followed her into her bedroom, and she turned her back to me, and I unzipped her. The zip went from the back of her collar all the way to the top of her ass-cleavage. I couldn't help sliding my hand inside her dress, and over her ass cheeks. She turned around and pushed her mouth into mine as her dress fell from her shoulders.

She was not wearing a bra, but wore a pair of purple silk bikini panties. She removed them herself, and turned to kiss me, pushing her naked body into me with her legs spread shoulder width apart. She selected a cute dress that went to mid-thigh, and I helped her into it at her insistence. She put on a pair of four-inch heels with it.

That means that she was not wearing bra or panties: the dress and her heels were the only clothes she was wearing. There was a crowd for the many features that were showing, and I noticed that she brushed her ass up against a couple of men as we squeezed through.

Our feature, however, was sparsely attended, and we found a couple of seats near the back, so there were some people behind us as well as in the rows below us. I flipped the arm rest up that separated our seats so we could sit closer. Our seats were off to the side in a darker part of the theater.

It was actually a good movie and I was enjoying it. After a while, I noticed that she slid her hemline up several inches, and she whispered in my ear as I had my left arm around her,

"Touch me, Jamie!"

I placed my right hand on her thigh. Her body is so silky smooth, and I slid my hand up her inner thigh as she demurely moved her left leg down and away to open up to me. I let my fingers play with her amazingly smooth inner thigh as she moaned softly. She saw a male patron watching us; he was ahead of us in the next row, but several seats away. She smiled at him and pulled her dress up nearly to her hips, and the guy got nervous and turned around.

I fingered her soft, jet-black pubic hair, just twirling it around my fingertips. She was moist, and I slid my finger slowly down along her pussy lips, and she gasped as I slid it into her. She breathed in sharply as it slid further into her, and she released her breath in little huffs, trying to control her breathing as she became more aroused.