Jamie's Story

So, I was a good little girl and behaved myself.

I felt his hands slide over my breast forms, and I watched his expression to see if he noticed anything weird, but he didn't. Just then, the song ended, and he led me back to the table, and so did Becky's no name partner (Found out later that it was Mark). Becky and I returned to Anna after another quick kiss for each of us from Tom and Mark before they returned to their table.

We were excited and talked and laughed together about our experiences with the guys. But, I received a strange look from Anna. We decided to have another drink and were just about to order them when our server brought refills for all three of us.

"Complements of the gentlemen at table four."

She said nonchalantly, and jerked her head, to indicate Tom's and Mark's table. They smiled at us and I was thrilled ... my first drink bought for me by a man. I gave Tom a sweet sincere smile and mouthed the words, "Thank you!" He nodded with a handsome smile.

God, am I falling for this lug? Yeah ... I guess I am! I was thinking to myself.

After a while, we started to talk about leaving, and Tom, Mark and another friend came over to ask the three of us girls back out onto the dancefloor for one more twirl. Becky and Anna started to groan a little and I told them,

"C'mon girls how can we turn down such handsome men? Another dance won't hurt us!"

Mark took Becky's hand, and Anna got the third man who is tall, light haired and quite athletic looking. All of a sudden, I was jealous of him with my girlfriend, but a slow tune started and we were all on the floor. Tom and I danced close and talked quietly.

His hand moved down my spine, and he slid the tips of his fingers into the pucker of the waistband at the back of my shorts, I felt them as they slid in almost to the top of my crevice.

"Tom, you are a naughty boy, do you know that?"

"Always have been, Jill honey!"

He laughed a very deep manly laugh, and I felt the vibrations through my fake boobs. He seemed to be dancing us toward the French doors leading to the patio in the back of the club. When we got close, he asked,

"Jill, it's kind of warm in here, want to get some fresh air with me?"

"Sure Tom!" I said sweetly.

God, I am in so much trouble now! I thought to myself! I know what 'want to get some fresh air' really means. But I wanted to be alone with him.

I couldn't make myself saying no to this man, but then, I didn't try either. We broke from our dance and walked out to a rather dark part of the patio. I am thinking that Tom has taken girls back here before. We stood in the shadows, and he kissed me. I mean, he really kissed me! My girl's heart is beating a thousand miles an hour, and I was breathing so hard.

His hand slid down over my breasts and my stomach, and then I felt him unbutton my shorts and slide the zipper down. Then, he pulled me close, still kissing me, and slid his hand down into the back of my shorts and inside my panties.

Oh, God! Oh, God! I was thinking. His strong hand felt so good on my soft bare ass as his large fingers touched very private places!

He started to move his hand around to the front, and when it slid over my stomach, and down toward my mound, I pulled his hand out and stepped away from him covering my face with embarrassment. Tom was inches from discovering my true identity. I quivered from head to toe, and breathed hard as I looked at Tom.

I might have told him any number of things at that point: I'm not that kind of girl, please don't do that! But I panicked! I told him the truth that he was about to find out for himself,

"Tom, you are a very nice man. Under other cir-circumstances, I m-might be a very lucky girl. B-But the f-fact is, Tom I ... I, uh ... I'm ... I am not a girl!"

I dropped my eyes and my head as Tom quickly withdrew his hand and took a couple of steps back. He looked at me for what seemed like an hour although it was likely only a few seconds.

"Jill, please tell me who you are! Tell me what you are!"

"Tom, do you see that pretty light haired girl in the sweater and blue jeans dancing with you friend?"

"Yeah! So?"

"Sh-she is m-my girlfriend Anna! The one dancing with Mark is our friend Becky. My name is Jamie and the two girls had the idea to dress me up this way for a night out with the girls. I am not gay ... I am in love Anna ... Becky rooms with Anna and me!"

My heart was pounding out of my chest as I continued; I hoped that he wouldn't deck me or anything. I quickly told him,

"I have to say that I was attracted to you as Jill, and if I led you on, or embarrassed you in any way, I am heartily sorry. You are a very nice man, Tom!"

I looked up at Tom and as he raised his hand to scratch the back of his head, I flinched thinking at first he was going to strike me. He laughed and said,

"Jill, I am not going to hurt you! I was starting to fall for you too, so I guess we have kind of a predicament!"

He put his hands gently on my soft shoulders, rubbed them a little and said,

"I am going to call you Jill since you are dressed as a girl. Jill, I am not gay either—far from it—but if things ever progressed with us, I would have liked to see you again ... as Jill, and in that persona, I could even see myself making love to you. As Jamie, we might go out for a couple of beers and a basketball game or something ... you do like basketball don't you?"

"Dyed-in-the-wool Bulls fan Tom! Plus, I am also a pretty fair racquetball player. Do you play?"

"Yeah, as a matter of fact I do, and I'm pretty good myself!"

"Hmm. We do have a problem here." I mused aloud, and then Tom offered,

"I have to be honest with you. As a solid hetero, I would not mind seeing you again as Jill. I mean it is only a dick, right. You are a lovely person and we would certainly have to discuss how Jamie fits in to all of this. Shit! What am I saying! You have girlfriend, you have Anna, who looks like a very nice person. Jill, what are we going to do?"

"Tom if you have a card, I would take it, but I will have to check on Anna's feelings. This was a spur of the moment thing tonight with the girls. They thought up this 'girl thing' for me so I can join them on their night out clubbing thing next week. Tonight was supposed to be kind of a dry run! This is so embarrassing, but I became their little project ... their little dress up doll!"

He looked at me, turned his head a little to the side, then he pulled a business card out of a leather card folder, held it out to me between two fingers and said,

"I am giving this card to Jill!" Then he slid it down into my bra.

In a soft and sweet girl voice, I said, "Understood, Tom!"

He moved in and slid his arms around me, and kissed me again with great ardor. My shorts are still open, so he slid his hand down my front, into my shorts and panties and over my neat, smooth triangle. He fondled me until it started to break through the tape.

"Can I ... see it, Jill?" he asked.

I reached down and pulled everything out, straightening my cock for him. He moved his hand over it letting his fingers play with it, then he pulled his hand out and slid both of them down the back of my shorts and panties, which then worked their way south to about mid-thigh. With both of his strong hands on my ass, he fondled them gently as he kissed me passionately.

I can imagine that he is aroused by tasting my lipstick, and sweet-smelling the body lotion Anna smoothed over my shoulders. I could feel my cock lengthen and harden. I felt his fingers slide into my crevice, brushing over my asshole and down over the back of my thighs. He didn't object when I slid my down his front, and felt his cock through his pants. It was thick, and becoming aroused.

He kept one hand on my silky smooth butt, and the other one he slid around my thigh to the front. His hand was playing with my silky hairless cock and balls, just massaging them until my cock hardened to it full proud four inches.

"Oh, that feels so amazing!" he said still fondling me. As he fingered and stroked me, I closed my eyes. Then I felt his breath on my crotch, and I quickly opened my eyes and said in a breathless female voice,

"No, Tom! Not that! Not tonight honey!"

He continued to touch me a little, and I shuddered everywhere, from the electricity surging through my loins. I was very jittery, and nearly shuddered out of control with my cock in his hand, so exposed in that semi-public spot. He looked up at me and smiled,

"You feel absolutely amazing, Jill honey!"

Standing up, he kissed me like I had never been kissed before, being held tightly in this strong man's arms, with his lips pressed into mine, and my cock still hanging down, still dripping a little pre-cum onto the patio flagstones.

He helped to put me back together and even volunteered to tuck me under as well as he could, and then fastened my shorts. He looked at me and said,

"Jill, baby, you are something else!" to which I softly said with a shy smile,

"Yes literally!"

We both laughed at that, and he kissed me again and then led me back into the club and to our table. He gave my still tingling ass, a couple of gentle pats before we reentered the pub. Anna and Becky were sitting at the table alone, and Becky was the first one with a remark as we approached,

"Well, darling were we a good girl tonight?"

Tom smiled, and I said, "Yeah, I was!"

Becky looked at me with some doubt, and said, "Uhhh huh!"

Anna's look was one I had trouble deciphering. It looked like a mixture of worry and jealousy. I needed to talk to her later. Tom bid the three of us goodnight and we got ready to leave. I asked Becky to get the car, and she understood after a few seconds that Anna and I had some things to talk over.

Anna looked into my face letting her eyes scan it from top to bottom. She says in a soft—almost sad voice,

"You said that you were a good girl, Jamie! What does that mean, exactly?"

"Anna, you have to remember that you and Becky put me in this situation? You made me a girl for the night. It can't be a surprise that a man would be as attracted to Jill, as they were to you and Becky. He reacted to me as Jill, touching and kissing me. When he got too close to my ... stuff, I stopped him and I told him who and what I really was. I emphasized to him you were my girlfriend."

"Well, thank you for that, Jamie!"

"Anna, you know I love you. But, he saw the pretty girl you made me, and reacted naturally. Damn, honey, I have a 200 IQ but I am getting really confused. I don't think there is a mathematical algorithm to explain any of this! Anna, who am I tonight ... Frankenstein's monster? You have to give me a little slack here!"

"I'm sorry Jamie; I guess I was a little jealous of Tom. I love you and trust you, darling!"

"Anna, my heart sank when you walked out on the dancefloor with that man, if only for a dance or two."

"Jamie, I will never ask you another question about tonight, and when we get home I want you to make love to me. I need you all to myself tonight! I need Jamie!"

"Alright honey, I want that too!"

I reached over and kissed her sweetly on the lips. Just then, a large hairy biker-type walked by our table, he must be the only guy in town still sporting a mullet, and he said,

"Damn dykes!"

This caused Anna and me to put our heads together and laugh. We heard a horn honk coming from outside to front door, and both said to each other at the very same time,

"Becky!"

On the way home, Becky became our chauffer as Anna and I cuddled in the back seat, making out like teenagers. Becky talked up a storm as she drove, mostly talking to herself though. I took Anna's lovely face in my hands and told her,

"I love you Anna!"

She started to tear up, and could see one single tear streaking its way down her cheek, and she had her head down a little, but raised her eyes to mine and she said,

"I love you too, Jamie darling!"

I leaned up against the door with my arms around Anna, who cuddled up against me with her legs curled up on the seat. We were quiet, and I just felt her heart beat, listened to her breathing ... and Becky's incessant chatter to herself.

At our place, Anna told me to get myself cleaned up and change back into Jamie. I heard Becky tell us,

"I am tired, and just want to turn in. See you guys in the morning ... I'll make breakfast!"

They gave each other a peck on the lips, and then Anna padded down the hallway to join me in the shower, helping me to scrub off my makeup. We soaped each other up, and kissed and fondled some. We exited the shower and wrapped towels around each other. I took a minute to remove my earrings.

When I walked out into the bedroom, I saw that Anna had already donned a pretty lavender shorty nightgown with matching panty briefs. I pulled on a pair of more 'butch' boxer briefs giving her something she can have the pleasure of removing later. I led her to the bed.

I have previously described her as petite, slender and having light brown hair and blue eyes. Her wavy hair, and the way she has it cut, causes a little nearly blonde curl to slip down over her forehead. I loved it because she always gave me a sexy giggle when I brushed it back off her face. She was sitting on the bed, and as she pulled one shoulder strap her nighty off her shoulder she struck a sexy pose, and that little lock of hair curled down onto her forehead.

I slid into the bed, and reached over to slide my hand over the creamy skin of her shoulder, and then brushed the curl from her face; she giggled, and I felt that twinge of excitement I normally get from her pretty features and her sexy manner. She looked at me,

"Hey, pretty boy, want some of this?"

She said that as she let the other shoulder strap drop, exposing her round firm breasts with their amazing puffy nipples.

"Yeah, baby ... I do!" I answered her question.

Then I took her nighty off, and as she laid back, she raised her cute ass as I slowly pulled her panties down exposing just her mound, and the downy-soft patch of hair lightly covering it. She moaned as I reached down to kiss her there.

I slid her panties down just a little further so I could see her lovely pussy just start to come into view, and I kissed her there, and stuck the tip of my tongue into the fold. I could smell her musk start to rise and involuntarily breathed, "Oh my God!" Anna moaned,

"Jamie darling, don't t-tease me!"

I pulled her panties, down and off, and moved my kisses down to her dewy lips, glistening with her sweet liquid. I could taste it on my lips as she gasped, holding her breath in, and then releasing it in little jittery huffs, and breathes,

"Please Jamie ... pul-ea-se! I need you baby!"

I moved between her legs as she opened them and I watched my cock slowly slide into her. She moaned and shuddered a little as I pushed in. She flutters her eyes open and looks into my face and, moaned,

"Oh, Ja-am-mi-ee! Oh yes, baa-byy!"

She grunted a little with each stroke into her, and when he breathing quickened, I knew that she was close, I tried to hold my own excitement off until she squealed, shuddered, and quaked into a strong orgasm. I pushed into her with a few strokes until I stiffened, and shuddered as I gushed deep into her with strong eruptive spurts.

We just held onto each other until the room stopped spinning, and the earth stopped quaking. In the calm aftermath, I looked down into that beautiful flushed, sweaty face. Her eyes were wide, and appeared very child-like. She closed her eyes, turned her heard and breathed out,

"Mmm, dar-rl-inn-g! Oh Ja-am-mi-ee! I love having you in me, loving me, fucking me!"

I rolled off her, but pulled her with me and she squealed ending up on top. She pushed her body down, trying to make herself heavier, and said,

"You're not going anywhere, Mister! Not until I say so!" then I rolled again, and she was underneath looking up at me.

"What about now honey?"

"Okay baby! You win! Now get up and make me a nice midnight snack, and the fuck me again!"

I told her I would, but like the view I have! We talked a little—just sweet sexual banter, and then after a few seconds of silence she became more serious, and asked,

"He gave you his card, didn't he Jamie. I saw it on your dresser."

I replied, "Well, this is something you almost never hear a man say to his girlfriend, but yes, he stuffed it in my bra!"

She giggled musically. "Jamie, you are too silly!"

After another period of silence, she quietly asked, "Are you going to call him?"

"I don't know. I told him that I was in a relationship and that you were my girlfriend. I also told him that I would discuss it with you, and abide by your feelings."

"What if I said 'go ahead and call him'?"

"That depends on whether I am calling him as Jamie or as Jill. If I am Jamie that means we will just get together for a burger and a couple of beers, and watch a Bulls game ... you know laugh, swear, slug each other on the shoulder. If I am Jill, I would meet him dressed and made up as pretty as I can, and let him take me out to dinner, with no more than a nice kiss goodnight."

After a pause I smiled and added, "Maybe I'll let him squeeze my butt!"

She giggled at my remark and then asked, "Is he queer Jamie? He doesn't seem like he would be!"

"No he's not gay ... and neither am I. Look Anna, I am not going to call him. As tempting as it might be, to be with a man as Jill, I choose to be with you as Jamie, for as long as you want!"

"So you will not call him if I asked you not to ... not even as Jamie?"

"As Jamie, I think that is my decision. I would never ask you not to associate with a girlfriend of yours!"

"Oh!"

I reached down and bit her gently on the side of her neck. I know it didn't hurt her but she still said,

"Ouch! Jamie!"

We quietly talked back and forth, I called her a big baby and we talked sleepily about her supposed injury for a little while. Then I felt compelled to say,

"We need to talk about Jill sometime. You know it is odd, but Jill has her own personality and her own set of wants and desires, completely separate and completely different from Jamie! You and that little cutie in the next room created a monster. So, we will need to decide on ground rules for our little Jill."

She yawns, and says, "Okay Jamie, we'll talk. I promise. Um, darling? Let' forget about any snack, I am fee-feeling so tir..."

I said goodnight to her but it was too late, she was already starting to snore softly. I kissed her softly on the neck, eliciting a sleepy "Mmm!" from her, and I fell asleep with my arms around her.

~ ~ ~

Part Two:

We woke in the morning to find that Becky had worked her ample body in between Anna and me, so I also discovered that I was spooning her, as she was spooning Anna. I do not have sex with her ... not for a long, long time, but Anna and I are both okay with her cuddling up with us on occasion. My morning hard-on was starting to press against the back of her thighs so she shifted her legs enough to let it slide between them. I could feel her slippery moist morning dew on me.

She had her hands around Anna, idly playing with her friend's breasts, and fingering Anna's puffy nipples. My free hand was on Becky's well-padded hip and when she started to push her butt back against me, but I pulled back to avoid any 'accidental' insertions.

Anna was half-awake for a while, and she said, "Becky, you moved away from me, come back up against me honey! It felt good!"

Anna turned around and moved in close to her, face to face, breast to breast, and thigh to thigh. They kissed and touched for a little while. Brenda turned around, pushed her ample breasts into my chest, and I enjoyed her sweet morning kitten breath as she kissed me with open mouth. She fondled my semi-stiff junk a little then rose and headed to our shower, telling me to play with Anna as she bounded off.