Jamie's Story Ch. 02

"Mmm, sounds delicious darling. Let's do it!"

We got up, showered separately, and dressed. We packed a basket; some sandwiches, fruit, a couple of yogurt cups, potato salad, and a couple of bottles of beer. We took to the road, headed down toward the lake. She was wearing a rather revealing halter top over short white shorts, and snow-white tennies. I was wearing a pair of cargo shorts, and a knit top.

I noticed the cars with males in them slowing down to take in a view of Janet's breasts, since they jiggled as she rode hunched over her handlebars. We heard a lot of horn honks, and a few wolf-whistles. One group of guys even slowed to pace her, and yelled,

"C'mon, baby! Put yur bike in the back and you can ride in style."

She laughed and said, "You guys are cute, but maybe another time!"

They laughed and moved on. She looked over at me, stuck her cute nose in the air, and smiled smugly. The clear message to me was, "see, other men find me attractive!"

We had a nice time at the lake, and she served us everything, even opening my beer for me—which had gotten a little warm on the ride. She acted like she was on a first date, and resisted my efforts, when I got too close, or too amorous. But she made sure I had a nice view down inside her top, and into her bra.

We talked about what was going to happen tonight. I told her that Becca was also coming over to help us, so it would be a good opportunity for the two of them to get to know each other, while I was out with Tom. I encouraged them to use my kitchen to cook for themselves or to out if they wished.

She seemed to be happy with that. It felt so good just sitting near Janet and looking out at the lake. But that was after a while, we started out trying to feed each other, which ended in a minor food fight. I lost the fight, but did end up with her body on top on mine, receiving a nice kiss with mustard and a side of potato salad!

We packed up, putting the basket back on the carrier behind my seat, and took to riding tour around the lake, and then headed for my place. More male shouts, and wolf whistles, since her impressive cleavage showed to best advantage, bent over the handle bars as she rode. She was enjoying it, but frowned a little when a couple of girls we passed said, "Hi handsome!"

At about four in the afternoon Becca arrived and she had Kim with her. I was surprised, but pleasantly so. She explained that Kim was a genius with hair, and could help in that regard. Plus, she knew all about Jill, and vowed to keep it to herself.

Kim entered, walked right up to me, put her arms around my neck and pressed her open mouth into mine, sliding her sweet tongue into me.

"We are going to make you such a pretty little girl tonight honey." She said with a giggle.

Kim likes me! I know from experience with women that consider me to be handsome, even if I am a bit of a pretty boy, but quite a lot of them like that type. I am thinking that I might give her a call sometime. A dinner date with this exotic Asian girl shouldn't hurt anything, or anyone.

When the three of them were together, I said, "Tom will be here at seven, and you guys will have to long gone before then, so it is just Jill here when he comes. Take each other out for dinner or something, Becca still has a key, and I will give one to Janet as well."

They all agreed, and wanted to get right to work on me. In my bedroom, they stripped me down to my briefs, and Becca made me up. Kim did my hair in a very soft sexy hairdo that framed my face perfectly, and Janet dressed me. I started to get hard with all the attention, and they tag-teamed giving me a single blowjob to make sure I was taken care of.

They ended up kissing each other as much as they licked and sucked me, and Kim let me come in her mouth. It was mostly Becca and Kim who serviced me, with Janet off getting my clothes ready. Becca was the one to tuck me under since she had done it before, and I was ready.

I was in a short blue dress, and four-inch heels. I felt very sexy. I got lots of touches and kisses primarily from Becca and Kim. Becca was right, Kim is really a sweet and nice person. I noticed that she left a business card on my dresser with her private number, and a note on it that said,

"Call me sometime, handsome!"

I smiled seeing that, and because of her exotic beauty I decided that I would call her. The girls were in the living room each with a glass of wine, and it was getting to be six-thirty, so I kicked them all out, handing Janet a key.

They all had to kiss me on my ruby-red lips, so I had to touch up the lipstick myself. One quick turn in front of the mirror told me that I was a very pretty girl tonight. I thought so too, and I noticed that I had changed from a boy to a girl on the inside as well. I felt like a girl ... Iwasa girl!

At seven, the bell rang and my heart skipped a beat. I walked to the door with a feminine sway, opened it, and Tom was standing there with a dozen yellow roses. He was stunned and could only say,

"My God, Jill, you are so lovely. We are going to have a nice time tonight." I could hear in his voice that he had a lump in his throat as he said that.

"Come in Tom, would you like a glass of wine or a beer?"

"Beer's good!"

He came in and slipped his arms around me and kissed me hard. My heart was beating out of my chest as I felt his strong arms around me. When I fluttered my eyes open, he was smiling. He moved his hands up and down my sides, and we sat and had our beers. The girls schooled me on the proper way for a woman to sit wearing a skirt, with one ankle behind the other.

After the beers, Tom said it was time to leave, and he opened the door to his car for me; a black Jag, with a soft tan leather interior. I made sure that my hem rode up a little exposing a descent amount of leg when I reached over to push his door open. He noticed, and slid his hand over my stockinged thigh giving it a couple of love pats.

We had a nice dinner at a very high-test restaurant, and over coffee, He asked if he might take me dancing.

"Yes, Tom, that would be lovely!" I said in a soft feminine voice.

He smiled when he heard the way I said that. We had such a nice dinner conversation, that never mentioned Jamie at all. It was like I was a girl he just met, and was trying to get to know. He really wanted to impress me, and he did; my woman's heart was falling for him.

We chose a club, and were sitting in a private booth, near the dance floor. We started right out, with me stepping as quickly as I was able in heels to a lively tune, and I was having fun. We waited on the floor, for the next song, when a man approached us and asked me for a dance. Tom smiled and said as nice as he could,

"Sorry buddy, this is a private party!" He was trying to be polite, but the guy insisted saying,

"Why don't we let me lady answer for herself."

Tom was very patient with this jerk, and just put his hand on the guy's arm, and slowly squeezed until the man winced in pain,

"The lady says no! Got it!"

"Yeah, yeah, no problem!" the guy walked away, and did a half turn still rubbing his arm and said, "Asshole!"

Tom apologized for that, and a slow tune started. From a normal dance pose, we moved in closer, and I put one hand on his shoulder, and the other around his neck. He pulled me in close and kissed me. I put both my arms around his shoulders, and spotted something strange in a dark corner. There seemed to be three girls sitting together, looking our way.

It was Janet, Becca and Kim! Those little kittens must have gotten curious, and followed us to see what was going on. I decided to give them a show, if a show is what they wanted. I kissed Tom passionately, and whispered to him,

"Touch me, darling!"

I looked back at the girls, and Tom's attentions to me caused Janet to get up, and grab the hand of a cute young guy, and as soon as they hit the dancefloor, she slid her arms around his neck and kissed him, I watched as they danced so close together, and talked animatedly. What were they saying? Did she give him her number?

About that time, Tom slid his hand down over my ass, and I made sure my butt was pointed toward the girls, and Tom found the hem of my dress, and put his fingers on my ass under the dress, and massaged me as I moaned my approval, and told him,

"Oh, baby, that feels so nice! Maybe we can take this evening to someplace more private!"

"Back to my place?"

"Okay, honey!" I said in a sweet voice, I looked in the direction of the two remaining little spies and pursed my lips sending them a kiss-off, and the giggled together as quietly as they could. I couldn't see Janet or her partner anywhere on the dance floor. "Where were they?" I was asking myself with a bit of concern.

Tom and I left the club with his hand on my ass. He opened my car door, and I reached over to push his door open like I did before, but this time I stretched so that I showed a lot of leg, and a panty triangle.

He noticed immediately, and slid his hand over my thigh, I gasped as his hand touched the bare skin at the top of my stockings. He let his fingers touch me on top of my panties, and I shuddered. He pushed the start button of his Jag, and we were off to his place. On the way, I worried a little about Janet. "What is that little chick up to?" I found myself thinking.

Tom had a large expensively decorated townhouse, like someone decorated it for him ... someone with very good taste. He gave me the fifty-cent tour of his place, and we settled into his lush couch with a couple of glasses of wine. The first thing he said was,

"I see that you had a cheering section tonight at the club!"

"I'm so sorry Tom, they helped get me ready, and must have followed us from the restaurant."

"Did we give them a good show honey?"

l leaned my head against him laughing and said to him,

"We sure did! Two of them anyway!"

He idly ran his fingers over my hair, and played with the edges a little as I leaned against him. I slid my hand slowly over his thigh. We talked quietly for a little while, then he got up to put on some soft music. His sound system was magnificent, and seemed to be all the best stuff.

He pulled me up off the couch, and we danced in our stocking feet very slowly to the music. I was loving being in Tom's strong arms, and love it when his hands roamed everywhere over my body. But deep inside the dress, under the makeup, and the silk and lace there was still Jamie. I decided to push him, and my worries about Janet out of my mind and just be Jill tonight, even if it is just for tonight!

He stopped dancing and we just made out in the middle of his posh living room with my stockinged feet sinking into his thick carpet. Then he took my hand, and led me, like a little girl, into his bedroom. I felt like a fairytale princess! He wanted to undress me, and I let him. He removed my dress, and my bra (wasn't wearing the breast forms) and I stood in front of him in just a pair of panties, and stockings. He put his hands on the small of my back and moved them down over my ass, pulling my panties down with them.

He set my penis free, and let it straighten. I closed my eyes as he stood and kissed me, moving his hands over my body. He pulled me in tight and put his hand on my ass, as my cock pushed up against him. Running his hands down my body to my ass cheeks, he held them tight as he squatted in front of me, and put my cock in his mouth. He gave me a slow methodical blowjob, as I luxuriated in the feeling of having my small silky penis in his mouth.

I shuddered, and just relaxed as I filled his mouth, and he swallowed it as I lowered my face with a blush. It embarrassed me, having come in his mouth, for a reason I don't fully understand. I was so jittery I thought I might fall apart. He led me to his king-sized bed, and he slid in after me, having removing his own clothes. He was naked.

Tom had an athletic shape, and about a six to six-and-a-half-inch cock, but it appeared to be very thick. I was on my back, and he slid in on top of me, letting his cock rub back and forth against mine. I was a weird, but very amazingly erotic feeling! I was loving it! It made me very hard!

We kissed as we slid our bodies against each other, and he kissed every part of my body from my lips to my ass, and down my thighs. He looked up at me and said,

"My God baby, your body is so soft. You feel amazing."

I adjusted the pillows he placed underneath me as I turned over, and my derriere was pointed skyward. I nervously moved my legs apart; it felt strange being so exposed and waiting for someone to touch me there! His kisses started at the small of my back, and went down over my ass cheeks, all the way down to my balls, and then back up to my anus. I felt him lick me there. Then I felt a finger at the opening, as it massaged the circular muscle of my puckered opening.

I felt something cold enter my asshole, as he slid in a lubricated finger. He moved it in and out a little very slowly, and then added some more cream, applying it deep inside me. He donned his condom, and I felt the tip of his cock at my opening. He told me that he would be very gentle with me, since it was my first time. I answered,

"O-Okay, darling. I-I'm re-ready!"

I moaned, and he pushed it in just a little—not even the whole tip yet. He started again, but slid a little further until his whole tip was inside me. It hurt, but I tried not to wince, concentrating instead on relaxing my muscles. It was the first time I ever had anything inside my ass.

My heart pounded in my chest as he gently grabbed my hips, and slid in a little more. I pushed my ass back, opening my legs as wide as I could, and tried to relax until I had his whole six-plus inches inside me. It was the most amazingly erotic feeling in the world, and my cock was starting to react, I knew that I would be coming onto his pillow covers.

Tom's strong hands were amazingly gentle on me as he massaged my ass cheeks leaving his cock inside me. Then he held me under my hips, and withdrew his cock, but not all the way. I knew what was coming. I was about to be fucked for the first time ... to lose my virginity! I was happy enough with Tom taking my cherry. He started with slow strokes, and I grunted a little each time he bottomed out. It was not long before he was pounding me with long even strokes.

It didn't take long before Tom stiffened and released inside me. It was such an incredible feeling that I came at the same time onto his pillows. We lay that way for a while, and he softened and pulled out. He pulled off his condom, and we lay in each other's arms cock against cock, thigh against thigh. He kissed me sweetly for a long time, and I could feel his cock start to harden again.

He laid me on my back, and I watched as he rolled a fresh condom onto his six-plus inch fire plug. He smiled down at me, and pulled my ass up on his lap as he knelt between my wide open legs. It felt so amazing to be to be in this rather submissive position, completely naked with my arms and legs open to him. I felt very so deliciously helpless as he reached under me to grease me up with his finger. I watched everything he was doing to me.

Then he took his cock in his hand, and slid it into me, with my ass up on his legs as he entered me. He started slowly again, but then leaned forward over me, and started pushing it in me hard. He grabbed my ass cheeks, spreading them, and pounded his cock into my willing little man-cunt.

"Oh Tom! Oh yes baby! Mmm, yeah, honey!"

That was the kind of thing he was hearing from me, and he loved hearing it. He was fucking me furiously and I came all over him in several spurts. This pushed him over the edge, as he grunted loudly, as he came deep inside me again. It felt very strange, but very erotic with his cum pulsing inside me. I had come twice on his chest and stomach while he was inside me, and I was still jittering from my orgasm.

It felt so free just to let it fly as I came with no consideration to where it was landing. When he pulled out of me, he collapsed on his back. I moved over and licked my way down his front, cleaning up the cum I spewed on him, and then I removed his condom. I gave Tom a slow soft blowjob until he stiffened again and pulsed his stuff into my mouth. His large balls felt so good in my hand as I fondled them, and squeezed them as he came.

It was a lot, or seemed like it but I swallowed as much as I could. I just couldn't let go of him, and kept licking and tonging the glans and shaft of a cock that I had trouble getting my hand around. After that, I collapsed on my back. We just looked over at each other and laughed.

Tom made me a little snack in the kitchen, and he asked me to make the coffee. He was in his briefs, and I was in a little light blue silk slip over bikini panties, I brought along in a little bag with some overnight stuff. I felt very sexy in that little slip! I liked the way the material slid over my naked ass.

We talked, and laughed. A dark cloud came over Tom's face as he started to worry that he might be latently gay, and I tried to assure him that he wasn't, and he should call Kim, or maybe Becca next week, and bed one of them—or both of them—at the same time! He laughed heartily and agreed thinking that the last one seemed like a very great idea. When I told him that I did too, we laughed our heads off.

We ended up back on the couch. He pulled me into a close embrace and we laid together talking until about one-o'clock when he had to get ready for a red-eye flight to New York. I dressed as well as I could, and he dropped me off on his way to the airport.

He was rather distant on the way to my townhouse, and just pulled away quickly after I was out of his Jag. I am guessing that he was starting to worry about having had sex with another man. I know that he had fun being with Jill this way, but was likely wondering if heshouldbe enjoying it!

I entered quietly in case the girls were still asleep. It was nearly two-o'clock, really closer to one-thirty or so when I tiptoed into the master bedroom, and saw two naked female forms intertwined on my bed. I slipped out of my dress and into a pair of shorts.

It was only Becca and Kim in my bed, with no sign of Janet. She was not down stairs, and she was not in the guest bedroom, so I thought she might have gone home.

I saw that Kim was on the far end, by herself, lying on her stomach with her lovely legs spread wide. I slipped into the bed, and smoothed my hands over her silky ass. She moaned, and said without waking fully, "If that is Jamie, or Jill, just put it in me, baby. Then she wiggled her little ass to make her point. I positioned myself between her legs, and slid into her already moist little pussy.

She lifted he ass, and I quickly pounded her until I came inside her. Her body was amazingly smooth with its beautiful olive skin. After I came inside her, I turned her over and she smiled, quietly asked for another go. until be heard a voice next to her say,

"I'm next, Jamie!"

It was Becca, with her legs spread wide beckoning to me with her hands. Kim watched with her head propped up as I approached Becca's enticingly open pussy lips. I was hard again and slid inside her, and started stroking her hard. I came just as she did, and groaned as I spewed my cum into the pretty slender blonde. We kissed softly and when I looked up, Kim was begging for more. I tried to beg off of any more sex tonight.

I reached over and whispered quietly in Kim's ear. "I have you number doll, and we can get together later. But the girls started teasing me, saying that they want some more of me. They said things like,

"lightweight!" "Pansy!" "Girly-boy!" "Quitter!" "Dickless!" taking turns with their taunts.

Just then, it was about two-thirty or a little after when I heard the front door open, then close. Soft footsteps were on the stairs and Janet was at the door, expecting only the other girls. But seeing me naked with Becca and Kim, she turned on her heels, and padded quickly into the guest bedroom and shut the door. I heard the lock turn from the inside.