Jamie's Story

Becky and I still have sex occasionally, by only at Anna's request to help our mutual full-figured friend over an occasional dry spell. Becky is a very good and energetic lover, and I look forward to our occasional trysts ... I love fucking her! She has the warmest and lushest pussy ever. But when she slides in with Anna and me, on an occasional morning like this morning, it is just kisses and light touches.

I took Anna in my arms and pushed my throbbing, thickening member between her legs and then easily inside her from Becky's stimulation. I stroked her until it was evident that we would not reach nirvana or anywhere close to it, but just build up a warm tingly feeling for both of us from the friction. Typical for morning sex sometimes.

I slipped into a pair of jeans and a sweatshirt, and watched Anna pull on a pair of shorts over her naked butt, and grab a thin soft sweater. We walked into the kitchen to see that our pretty flat-mate had already made coffee and was working on breakfast for us. She saw how underdressed she was wearing just a pair of bikini panties and said,

"Wow, I am really underdressed for this party!"

With a naughty giggle, our free spirited friend bent over with her ample breasts swaying and pulled her panties off so she was completely naked. Anna and I laughed at her antics. She came up to me and pushed her body against mine with her a breast in my face as she asked,

"Want a little breakfast, Jamie honey?"

When I looked at her proffered breast as the possible breakfast source, she swung around and plopped a plate of eggs, hash browns, and sliced strawberries in front of me. We all laughed, as she turned to get a plate for Anna, saying over her shoulder,

"I'm not a cow, Jamie!" and I quickly retorted,

"Oh yeah, well l really like the way you mooo-ve!"

"Droll Jamie! Very droll!" She answered with a smirk.

We ate breakfast with Becky taking a seat opposite Anna and me. She dug into her food with great vigor, jiggling her breasts attractively as she did. Anna and I both stopped just to watch her. She looked up at us with half a mouth full of food and asked,

"Whah?"

Anna and I looked at each other and laughed. She shook her head and went back to cutting, forking and jiggling. Becky is a wonderfully natural person ... part of the reason we love her so much!

We all talked about what to do today—a day off for all of us—and we decided to take a trip down to the lake, with our roller blades to follow the paved path around it. It should be about a four to five-mile skate and just a nice day in the sun. I wore a pair of cargo shorts and a knit shirt, the girls were both in cotton halter-tops with string ties around their necks, and very short, running shorts.

They are both showing some cheek below, and both have a very pleasant 'jiggle factor' going on up top. I was a much faster skater than either girl, but I hung back a bit. Mostly to give them their space and to avoid all the 'chick chatter,' to watch their cute little asses in their short shorts, and just to see what might happen out on the trail.

Sure enough, the girls attracted the attention of a couple of young guys who looked like they lived in the gym. They were muscly and handsome, and skated along with the girls chatting them up pretty good. With their attention on these guys, I skated up a little closer so I was nearly behind them.

A lot of what's your name ... my name is ... where are you girls from ... where are you going after ... you girls are so hot ... just your standard hitting-on, bullshit kind of chat. I think that Anna caught sight of me but wasn't obvious about it, and decided to tease me a little with this guy. She decided to stop for a rest, sitting in the grass looking at the lake, Becky followed and the guys sat with them.

I saw Anna look around behind her carefully to see if I was watching. She had something in mind, but I didn't know what her game was. If it came to some kind of showdown, with me trying to wrest my girl away from them, I wouldn't be able to take these guys on—not by the wildest stretch of imagination. I had to rely on Anna's good sense to blow them off at some point.

Since she seemed to be happy playing her game, I seized on another option. I looked around and saw a young woman sitting by herself. She was very pretty, slender blonde. I skated a bit past Anna and Becky, and stopped by this girl and said "Hi!"

"Hi handsome, I'm Rebecca. Are you here by yourself?

"Um, not anymore! I'm Jamie ... mind if I join you?"

"Pull up some grass and have a seat!" She said cheerfully.

I perched next to her as she looked off across the lake and continued, "I love coming here, it is so calming, so Zen. You know?"

"Yeah I feel the same way. I hate to intrude on your Zen experience, but I know of a great little restaurant just around the bend by the beach!"

"Jamie, are you hitting on me?

"Mmm, not really, I am here with a couple of friends, but I lost track of them."

"Well, maybe I can help you there, Jamie honey. Would it be the pretty brunettes with those two gym-rats, back over there? The light haired one seems to be awfully interested in our conversation."

"You are a smart girl Rebecca, and a pretty one, but you are right!"

"Why thank you, kind sir! But, I think we are about to have company. Your friends have blown off their very large suitors, and are heading this way. The pretty light haired one gave hers a kiss on the cheek though, and I thought she handed him something."

I got up and so did Rebecca. She was a little unsteady on her skates after sitting for a while, and grabbed hold of my arm to steady herself. I looked at Anna with Rebecca still holding onto my arm, and I said,

"Oh there you are! I lost track of you, and didn't see you sitting there, dwarfed by that huge guy rubbing you back under your top honey."

Anna was trying to make me jealous, and she knew that I knew!

"I stopped to ask this woman here ... her name if Rebecca ... if she had seen the two of you but she hadn't! We were about to go out to lunch, would you girls like to join us?"

I was really sticking it to Anna, making Rebecca and I a couple. Rebecca was trying to stifle a giggle.

"Sure, Jamie! If you say it, I believe you darling!" Anna says with a sly smile.

Then to Rebecca, "Hi, I'm Anna, and this pretty thing is also a Rebecca—we call her Becky. Thank you for looking after my wayward boyfriend! Would you two like to skate along with Becky and me? We are just about to stop for lunch too; I know a great little restaurant just around the bend by the beach!"

Rebecca giggles at hearing the same line twice from two different people, and said,

"Yes, um if it is okay with Jamie, we would love to join you two girls ... if we're not intruding. By the way my friends call me Becca, and you should too."

Rebecca was leaning on Anna a little too, for teasing me.

"No of course not, c'mon you two love birds!" Anna said with a wry smile shooting me a 'loaded' glance.

So the four of us hit the trail again, and I pulled Anna back a little as the two Rebecca's continued on. I asked Anna,

"Well, what happened to your very large boyfriend, it looked like you were enjoying your back and neck massage?"

"Jealous Jamie?"

"Yes I was actually, but that was the point wasn't it?"

"Mmm, maybe ... maybe not!"

"Anna. My sweet darling, I know you better than that!"

"So, what's up with you and your pretty little blonde girlfriend, Jamie?"

"Jealous, Anna?"

"Okay, okay! Touché!" Then a little more thoughtfully she said,

"Jamie, I was very surprised and jealous seeing how quickly you were able to attract such a pretty girl! I guess, um, I was a little jealous of Tom last night too, and I just wanted to make you worry a little ... that guy proved to be very useful for that purpose!"

"Well, you certainly landed a couple of very handsome muscular catches yourself, and I was jealous. Could you see me trying to chase those men away from you? No way, but I found a way to solve the problem without getting the crap beat out of me."

"Jamie, I would never have let that happen to you! I have to say, I was very impressed with your clever solution to that situation. But you took for granted the fact that your little plan would work on me! And I know you would not make me fight Tom to recapture your affections." She said.

"Maybe, but I did not intend to make you jealous with Tom. I was a little confused by my internal 'makeover' dressed as Jill. It is something we will have to talk about later—the three of us—to decide what Jill's boundaries are when she is out. And, what Jamie's are when you to little monsters are in the arms of other men, dancing. You know, to decide what's allowed and what's not."

"Yeah, we should do that tonight. You can even invite your new girlfriend Becca along! Actually Jamie, I kind of like her ... she seems very nice! Plus, I think she had you figured out before you even sat down ... and she looked after you for me!"

"Okay, let's do it tonight. One more Rebecca who knows what a fruit cake I am won't matter."

Anna stopped, looked at me and said, "Jamie, is that how you see yourself when you are Jill?"

"Well, let's just say I'm very confused right now. I love you and Becky for helping me find a new aspect to my personality, but it is new and I am still trying to find my way through it. I like being Jill and want her to have some freedom, but I want her to be a nice person y'know and not just a slut or anything. Is that weird, honey?"

She laughed heartily and said, "Yeah, it is! But we'll sort through it."

Anna put her arms around me and said as she hugged me, "Don't worry honey, Jill will find her way, and Becky and I will help her with that!" She said and kissed me sweetly.

Anna and I notice how far ahead Becky and Becca had gotten, so we skated faster to catch up. The two Rebecca's seemed to be getting along quite well, and I was thinking that we might have another girl for our upcoming girl outing. Anna skated up behind Becky and grabbed her around the waist almost pulling them both off the path and onto the grass. I skated up a little easier and put an arm around Becca's waist, she smiled as she moved in closer.

We all finally reached the restaurant and had a great time over sandwiches and beer. Becca and I sat on one side and the girls were facing us, and Becca took the freedom to lean toward me, and give me polite little touches. Mostly, I just sat back and watched the girls talking and laughing.

As I watched Anna interact with Becca, I knew what she was thinking: she was thinking that the new girl fit in quite well, but bore some close watching around me! During a lull in the conversation, Anna said to her,

"Becca, we are going to have a little discussion at our place tonight; Becky, Jamie, and I, and we would love it if you could join us. I can give you the directions, and it doesn't have to be late. Since you already have Jamie figured out, I thought your input might be useful."

"Well, I was going to, uh ... oh what the hell! Sure I would love to!"

"Great! Jamie dear, borrow a pen from our server will you?" She took a business card from her pocket, and drew a map on the back,

"Okay, here are the directions to our place. We can put something together, or order out—pizza or something."

Becca looked puzzled and she quietly asked Anna off to the side, "So what's this big mystery we have to solve regarding Jamie?"

"Well, Jamie is kind of a special person. He is very bright— like genius level, bright—and has recently added some complexities to his personality, so we just need to help him um, figure some things out. You will see when you come over." She smiled and in an excited voice, added,

"Becca, I am so glad you are coming over ... it will be fun!" Becca answered her,

"I am too! Becky and I are practically sisters by now; she is so fun and so cute. And, we are all going to be such good friends. I mean I have friends, but not like you guys." The she whispers to Anna off to the side,

"Anna, Jamie is so handsome and so clever, the way he engineered your coming to him by pretending to hit on me. He saved himself the embarrassment of having to confront those big men you and Becky were using to tease him ... come to think about it, that might be an interesting story all by itself!"

"It might be, but we need to focus on Jamie. You know Becca, you seem to be very perceptive."

"Well I am a bit of a loner—I mean not ax-murderer loner—but I tend to stand back sometimes and just observe people. People reveal a lot about themselves when they don't know they are being watched."

Anna smiled, I picked up the tab for us, and we skated back to the car. Becca returned to hers with her hand-drawn map stuck in her bra, to meet us at the apartment. I ask Anna what was up with those two gorillas they were flirting with, she slowed down letting Becky get ahead of us a little, and said,

"Well, you should ask Becca because she seems to have us all figured out. That's why I invited her to our place to help us figure out Jill. She is smart and an objective third person."

"Anna, Becca told me that you handed something to that big guy ... did you give him your card?" I asked her in a low voice.

"Well Jamie, I just might have, I really don't remember!" she answered curtly, with a raised voice.

"Anna, you do remember that we are in an exclusive relationship. I have always honored it; will you honor it as well, if that gym-rat gives you a call?"

"Well ... of course Jamie! W-what do you expect?"

She said curtly and skated ahead toward Becky. I knew she was lying, but decided to let it drop ... for now!

So we drove back and at the apartment, the girls busied themselves trying to see what they could put together for dinner, and they decided on stir-fry chicken with steamed rice. They started getting everything together before Becca got here. Ten minutes later, she arrived, I let her in and we both heard Anna yell out to me from the kitchen still a little miffed regarding my questions about her new large economy-sized suitor,

"Jamie, can you entertain our guest while we get dinner ready? No tongue, but a little music and conversation might be nice!" She still has a bit of an edge to her voice.

Becca stifles a giggle over hearing Anna. I noticed how Anna sidestepped my question about her large friend from the lake. I know that she always carries a couple of business cards with her, but she only had one left when she handed it to Becca. Mr. gym-rat must have the other.

I gave Becca a kiss on the cheek, telling her that Anna was just kidding. I suggested that we pick some music out together. We crouched very close with our faces almost touching as we thumbed through Anna's CD's and I got a little twinge as her arm brushed against mine. She sees something she likes, and she touched my arm again.

She selected a couple of things, and as we stood, she was almost in my arms. We looked into each other's eyes for two or three seconds in a palpably intimate moment between us, and I turned to put the first one on.

Becca calls out to Anna, asking if she minds her dancing with me. Anna said cheerfully, "No, go ahead honey!"

Becca and I slid into an embrace like two puzzle pieces coming together. As we danced slowly to the music, she pushed her body into mine a little closer. Her body felt soft and warm. Her intoxicating body scents filled my nose.

Then I felt a tap on my shoulder, and Anna cut in to dance with me as the two Rebecca's danced together. Anna felt my cock rubbing against her, and looked up into my eyes with a knowing smile.

I kissed her on top of her head, she raised her face to me, and I kissed her on the lips, pulling her close. She slid her hand down my front, and said,

"Mmm, Jamie! I hope I am the one who caused that!" I only half lied to her when I said,

"Yup, you know you did baby!"

She put her head on my chest and purred like a satisfied little kitten. We completed stir-frying and decided over our meal and a bottle of wine to begin the journey into the Jamie/Jill phenomenon. Anna started the ball rolling,

"Becca, some few days ago, Becky and I were planning a night out clubbing—a 'girl's night out' so to speak—for next week and Jamie seemed worried about what we might be up to, so Becky told him he would have to come along to find out. Then she and I got the brilliant idea to dress Jamie up, and make him up as a girl so 'she' could go along with us. He is not gay, but as you can see for yourself, he has quite delicate features, and a makeover would be a dream." She took a slip of her wine,

"Well, we did make him up and the pretty little shit really looked like a girl! We decided to try her out in public, just for a beer and maybe some dancing—we called her Jill to give her a separate persona. Becky and I usually dance with some men when we go out, with light touches and kissing being okay, but nothing much further." Another sip and she added,

"Well, Jill met a guy named Tom she liked, and she let him touch her to the point where her true nature was about to be discovered. Tom is not gay either, but he had no problem kissing and touching Jill even after she copped to her dual nature. So the issue is this: what are Jill's boundaries, since Jamie is okay being with a guy as Jill, but would never do that as Jamie." After a slight pause she asked,

So, what do you think?"

Becca nodded throughout the explanation, and at the end of it, she said,

"Whew! I thought you guys were an interesting lot before, but I had no idea! First off, I think that Anna should set boundaries for Jamie as Jill and Jill should respect them, since they are in a relationship. You two are a couple! The boundaries can be as wide or as narrow as Anna is comfortable setting. Jamie as Jill is stepping into another persona." She took a sip of wine, ten added,

"This is not a case of dissociative personality disorder—multiple personalities—where one personality completely shuts down while the other one takes over. Jamie is the one making the decisions for Jill, but she may want wider boundaries to explore her possibilities a little ... to let someone kiss her, and touch her to see what that is like ... that's only natural. You girls allow that for yourselves! Do you see what I mean, Anna?"

"I guess so!" said Anna thoughtfully, "But I am not sure how far I want Jill to go. The ultimate would be sex ... anal sex in this case, and I am positive that I am not comfortable with that! Oral sex, I don't know ... possibly getting but not giving might be um, acceptable. It is certainly much farther than either Becky or I would ever go on our nights out together!"

Becky says, "Well, since we put Jamie into this, I think Jill should have wider boundaries. Being dressed like that does something to you; you play the part, walk the walk. Jamie as Jill becomes a girl! Shouldn't she be allowed to explore that a little?"

The discussion when on, and since I was the subject, I just listened to the girls. It all really came down to what was I comfortable doing as Jill, and what was Anna would allow. So the girls decided that Anna should set the limits, and Jill should abide by them.

The tripartite committee also decided that the girls can allow chaste kisses or light touches from men and when I join the girls as Jamie, I would have the same limits dancing with other women. This was the single weirdest discussion I have ever been involved in!

The only other issue was that of Tom, who might want to date Jill. Anna decided that she was uncomfortable with that, but if Tom ever showed up at a club where all the girls were, Jill's agreed upon boundaries would apply ... for now! Anna reluctantly agreed that Jill could decide whether to accept oral sex, but not to give it, and only with men she knows to be clean.