Jamie's Story Ch. 02

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Continuing Jamie’s tale of self-discovery.
16.3k words
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Part 2 of the 4 part series

Updated 06/08/2023
Created 07/04/2016
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Michael142
Michael142
543 Followers

Author's note: This next chapter is the story of Jamie's attempts to explore his sexuality on his own, after Anna. He will also explore Jill's new persona dating Tom and maybe others. There is a lot of sexual activity in this chapter, which may seem excessive or gratuitous to some. It's my belief that there is just as much sex as is necessary to tell the story of Jamie's search for that one girl (or person) who matters most. Thank you, M142.

Part four: After Anna.

Moving past my relationship with Anna, I felt that I had just improved my life one-hundred percent, and was excited at the prospect of having some control back. Tonight, Becca, a pretty and smart girl, was waiting for me with breathless anticipation. Life was good!

So, do I see myself simply engaging in a sexual romp through all my closest female friends, and maybe some others? Yes! Partially! But I still have some questions to answer about myself. I'm twenty-seven, so where am I going in my life. I have known Anna for thirteen years, and that relationship has blown up in my face so I am free, but free for what?

I love Becca for her beauty and her brains, for her sensitivity, and for the confidence I see in the way she moves. But I still love Anna, she is sweet and a friend over the years, and I appreciate the acceptance she has given me for all my physical shortcomings.

I see Janet in the office every day; she is part of my office routine. So why does my heart skip a beat whenever she bursts into my office with the solution to one of our thorny office challenges. I start to lengthen and thicken when she put a tiny hand on me, looking over my shoulder at the computer. I like the way she always calls me 'boss' even though I ask her to call me Jamie instead. She is so cute in her oversized glasses; I have to keep pushing them back up her cute nose for her.

Not the least of my female friends is sweet Becky. Anna used to share me with her when she was in a romantic slump and depressed. She is an amazing lover with her full lush body, and I love the indomitable energy she puts into her lovemaking. I can get so lost in her dark beautiful truthful eyes. Yes, I love her too!

And what about Jill? Do I still want to do that ... what ... crossdressing? I have never had any homosexual urges, but would I really give myself (as Jill) to Tom, or to any other man? What will that do to our guy to guy friendship. I like the camaraderie with him and his friends, and with my old friends from my baseball days. So where does she fit into my future?

At the office, Janet was getting very frustrated at having to tell me things twice, with my mind occupied with all of these thoughts. I took Janet by the shoulders, and told her what had transpired. She knew a lot about me already, and she told me before that Anna, while a sweet girl, was going to cheat on me. She looked in my eyes and said,

"Boss, do not get into another relationship too soon, date around a little. You deserve some freedom for yourself, and for Jill. Let her date a little too!"

"I will, I promise! Now, help me celebrate a little, I know you are waiting to give me one of your nice warm hugs!"

She threw her arms around me, and forgetting where we were, she pressed her lips hard against mine. This is pure Janet! She celebrates every little victory with an excited hug and kiss to a teammate, whether it is me, Casey or Margaret our two testers, or Lindsay our unit admin assistant. She is a happy, energetic, guileless creature, and none of us mind her displays of affection—even Margaret, who seems to like it!

"Aw boss, you know me too well, but I'm so happy for you." Then she kissed me again, and blushed a little.

"Jan honey, I keep telling you not to call me boss. We are members of a team remember? You, Casey, Margaret, Lindsay and me!"

"Oh yeah, sorry boss—uh Jamie!"

Janet is one of the sweetest, kindest, and most brilliant women I have ever met, and she calls me boss. She is about five years younger than I am, and started working on her PHD in systems analysis when she was seventeen completing it while still nineteen.

She is bespectacled, with glasses that are obviously too large for her pretty face, and they keep sliding down her little nose. I often push them back up for her as we work which unvaryingly elicits a "Thanks, boss" and a giggle from her.

She can pull apart a computer sub-routine, tens of thousands of lines of code, and put it back together faster than anyone on our team. She prefers the keyboard to a mouse, and types so fast it sounds like a machine gun. I have no idea what her IQ might be, it is likely far off the charts, like many in this business.

She is very cute, and petite, with a set of breasts too large for her small size. I have thought about dating her before, but she is a direct report, and that makes it difficult.

She has a very easy temper; once when she caught me looking down her blouse, she calmly said,

"My eyes are up her, boss; those are my little boobies!"

Then she smiled, and her nimble fingers flew across the keyboard, as she continued parsing a set of code, looking for a problem. I of course, went back to looking down her blouse when I could. Those round, milky melons were too compelling! But today, she was happy for my having found my freedom.

She never cared for Anna, but was too sweet to ever say that—but I knew. Janet knows all about Jill—she's the only team member who does. In fact, she knows more about me than anyone else in my life.

~ ~ ~

Becca was there when I opened the door, and was a vision in a pretty blue party-style dress, stockings and heels. I told her,

"I know I offered to make it for you, but you look so pretty, I'm taking you out to dinner instead! Anywhere you wish!"

I put my hands on her hips, and slid them around her back pulling her into a kiss she wouldn't forget for a while,

"Whew! Jamie! Where did that come from honey?"

We found a nice little restaurant she liked and she was so happy she was almost giggly. We had a nice toast and waiting for our meals, she asked in a sincere voice,

"What's next Jamie?"

"Oh, Dinner, maybe dessert, but sure another glass of wine—this stuff is good!"

"Jamie!!!" She scolded.

"Alright! I want to be with you for a while Becca, I like you for a lot of good reasons. But you should know that I intend to date a little—both Jill and me. And so should you, that's only fair!"

"Jamie, I am not trying to trap you into another relationship, but I just hope you give me some attention while you are looking. But, if you are going to be with me, I would ask that you practice safe sex with any others."

"Of course I already understand that. Um, I would need to stay at you place until I find my own place. Maybe you can help me with that!"

"Sure! But I want visitation rights to your new place, and in exchange I will throw a house warming party for you!"

We lived in Becca's small apartment, until I bought a townhouse with more room, and she proved to be a very good, and responsive lover. My townhouse was two stories with three bedrooms upstairs, and a semi-private courtyard beyond the double doors from the dining area of the kitchen.

It's my place but she stays over most nights, still keeping her own little apartment. We are not a committed couple, and she does date other men, and often has Becky over; sometimes here, and other times at her place for God know what! When Becky stays here, some tri-partite sex is allowed. Becca happily allows her dear full-bodied friend to have some time alone with me.

She did organize an open house for me, with each of us inviting some of our friends and co-workers. She helped with the invitation list, and insisted on inviting both Becky and Anna, along with a some of her friends and selected co-workers. There was no response from Anna. She also invited Tom. Becca agreed to be a co-host, and help me with the guests.

This was all decided one night, as we laid in bed, face-to-face, hip-to-hip, and thigh-to-thigh, still naked after making love. We were giggling and occasionally kissing, as we talked quietly with lips nearly touching.

I warned Becca about Janet, being a bit on the 'huggy-kissy' side, and Becca warned me that the head of the reference library, Kim Nguyen, had a crush on me just from what Becca had told her and close friends at work. She didn't go into any details, but indicated that she could be something of a Dragon Lady, albeit a very beautiful one. At the end of our intimatetête-à-tête,I smiled and asked her,

"You tired?"

She giggled and whispered, "Huh uh! You?"

I kissed her briefly and answered, "Huh uh!"

With that, I flipped her over, and once again she was on her back and I was between her open legs. We went straight to it for fifteen minutes and she came twice before I relaxed and enjoyed the extreme pleasure of releasing my cum inside her body, in several shuddery spurts. We separated in sweaty heaps. We just looked over at each other, clasped hands, and laughed ... full-throatily and loud.

~ ~ ~

Part Five: The Party.

The evening of the party arrived, and we were ready. Becca hired caterers and a bartender so we could be good hosts to our guests. I wore an expensive pair of slacks, loafers, and a blue silk shirt. Becca looked beautiful in a pink dress with elastic at the top which gathered just above her breasts, baring her lovely arms and shoulders, and tied at the waist.

I told her how pretty she looked, and thanked her for setting up the party. She gently placed her hands on each of my cheeks, and pushed her mouth into mine in a sweet mouthy kiss, and said in a soft, low voice,

"Thank you darling! And, you are very welcome!"

The caterer and bartended were there and ready for action. It was agreed that we would greet the guests together at the door when we can, since some of them would be unfamiliar to each of us. Becky was the first one to arrive; she arrived alone. She looked pretty in a nice dress that showed a lot of her ample cleavage.

She immediately clasped Becca with a warm hug and a kiss. Then she turned to me, her old triumvirate partner and long-time friend, and put her arms around me with tears in her eyes and kissed me sweetly. Then she said,

"Jamie, darling! I am so, so happy to see you again. Please don't be a stranger to me!"

"Welcome sweetheart! You can knock on my door whenever you wish—you know that!"

I kissed my friend briefly but sweetly before other guests caught our attention. Mostly my team members arrived at the same time. Casey, a mild-mannered man shook hands, and entered the living room where he was immediately intercepted by the catering staff, and shown to the bar. Lindsay showed up separately, kissed me and Becca each on the cheek, and joined her co-workers.

Janet immediately threw her arms around a very surprised Becca, and kissed her hostess full on the mouth saying,

"You have to be Becca! Jamie told me about you, and I feel that you are already a friend! Becca answered,

"Well, it is nice to meet you Janet! Come and find me later so you can telleverythingJamie told you about me!" Janet looked at me, gave me hug and kiss and whispered,

"Sorry boss. I'll just give her name. rank and serial number!"

"That's okay Jan, you can tell her what she wants to know. They're not national secrets!"

"Oh, boss! You're so silly!" she giggled.

She moved in to join Casey, and Margaret who meekly slipped in with a muted hello to us. Becca move in to chat with our guests, when the doorbell rang again and she asked,

"Jamie will you answer that please? I want to get to know your team members." Then to Janet she said, "Come dear, sit next to me!"

Janet looked back at me with worry in her eyes, and then followed Becca to the couch, where a pretty young catering staff member offered treats. I laughed at Janet's predicament, and turned to answer the door. I opened it and was greeted with the sight of perhaps the most truly beautiful woman I had ever seen. She was petite, slender, with perfect dark almond eyes. He jet-black hair agreeably framed her gorgeous face, falling well past her shoulders to about the middle of her back.

She was wearing a full length, very tight dark purple dress, which showed off a pair of lovely olive-skinned breasts, with a leg slit nearly to her hipbone. For about two and one-half seconds, I took in the beauty her face, and her lovely heaving breasts and all the way down a slender, shapely leg sticking out from the long slit, ending in four-inch matching silk heels. But before I could find my voice,

She tiptoed up and with a hand around my neck, she opened her ruby-lipped mouth and pressed it into mine. I had intended to keep my hands safely on her hips, but she pushed her body in so close, they encircled her tiny body. After the kiss, she slowly blinked her incredible black eyes, and in a silky-smooth voice said,

"You must be Jamie. I have heard so much about you from Becca, darling!"

As she gave me an inscrutable smile, I finally recovered enough to respond. "You have to be Kim. It is so nice to meet you; you look very lovely tonight!"

I quickly broke our embrace, and led her into the living room with my hand in a safe zone on her back just above her waist. Becca quickly rose to greet her co-worker.

"Kim! So nice to see you; I'm happy you could make it—you look amazing tonight sweetie!"

The two girls hugged, and kissed each other perfunctorily on the cheek, and Becca introduced her to me formally,

"Jamie darling, this is Kim Nguyen, who heads our research library." Kim just smiled and I said,

"Yes, we've already met! Enchanted, Ms. Nguyen!" I took her hand and kissed the back of it continental style.

As Kim entered the living room, she turned and smiled back at me and pursed her lips, then was escorted to the bar and the buffet table. Becca took my arm and as we returned to the living room, she asked,

"Well, how was it darling?"

"Amazing! Sexy! Scary!" I answered, and Becca laughed and said,

"Don't worry honey, Kim is really a sweet person, and the 'Dragon Lady' act is mostly a façade! But, be careful anyway honey!"

"Becca, as incredible a beauty as you are, I have to say, she is the single most beautiful woman I have ever seen!"

Becca laughed and said, "Yes, she sure is! If I was a man,I'dwant to fuck her!"

We were laughing at that when the doorbell rang, and it was Becca's turn to answer it but I decided to assist her. Becca opened the door, and saw Anna, and Tom who arrived separately, but at the same time. Becca put her arms around Anna without hesitation, and gave her a warm hug, as Anna looked over her shoulder at me. Becca said,

"Anna, honey! I am so happy you came ... welcome." Then to Tom in a bit sexier voice, "Hello handsome! Nice to see you again!"

Anna gave Becca a smile, but moved on past her to me. She put her hands on my shoulders, kissed me sweetly on the cheek near my ear, and whispered,

"Hello, Jamie darling!" when she pulled back she had tears forming just enough to add a sparkle to her pretty golden brown eyes.

"Hi, Anna, it's nice to see you again, you look so lovely tonight!"

She did too! I know her wardrobe enough to know that her short, tight electric-blue dress was something new—recently bought—perhaps for tonight's party. Tom received a hug and a warm kiss from Becca, as he had one hand on her waist, and the other patting her on her shapely little ass. I watched as the kiss lasted longer than just a hello!

I thought to myself, what is Tom's problem, hitting on a woman he knows I am interested in. They talked quietly but briefly as he broke from her to take my hand, in a strong handshake. Then Tom looked past me into the living room, he caught sight of Kim, and told me,

"Excuse me buddy, but I have someone to say 'hello and I love you' to."

Without turning, I knew he was talking about Kim. I laughed and said,

"Lovely, isn't she!"

Tom clapped me on the shoulder and as he moved on past me, he said, "That's only to beginning buddy, I let you know how it ends."

Other guests arrived and were greeted either by either Becca or me, or both, but we were both busily engaged in keeping their guests happy. The music was lively, and a few couples were dancing to it. Tom was off in a corner with Kim, and seemed to be making some headway.

Anna waited until Becca was otherwise occupied, and approached me, her pretty eyes looked up into mine as her fingers played with the buttons on the silk shirt she bought for me. She gently placed her delicate hand flat on my chest, and asked,

"Jamie, um, at the next slow song, can you come get me ... for a dance?

She motioned with her head to the darker and more private courtyard, where some guests had moved to talk and dance. I just smiled down at my former lover and quietly said, "Okay Anna!"

It seemed like all twenty of the invited guests arrived, and were having a good time interacting and getting to know each other. It looked like some new friendships were being formed, particularly boy and girl friendships! I was momentarily distracted by the sight of Tom and Becca standing close together, and quietly talking in the darkest and furthest corner of the courtyard area.

A sense ofdéjà vucame over me, but I didn't want to look this time. As I turned, I bumped right into Anna. She took my hand and said, "Dance with me Jamie!" as she led me into another corner of the courtyard.

She slipped a hand up my chest to my shoulder, and I put one on her waist and held her other hand in close. She looked up at me with her golden eyes wide. She was so pretty, and she had a way of looking so childlike and innocent. It always got to me, and she knew it.

"Jamie, you have a very lovely place, and Becca looks beautiful tonight." She paused to let the first part of her message sink in, then said,

"You know that some large piece of my heart will always belong to you Jamie. I guess, I just want to let you know that I took you for granted, and that's a mistake I will never make again. I just want to be in your arms, and have you kiss me the way you used to." She looked up at me hopefully.

I stole a glance around to whatever was happening in the opposite corner, and saw that Tom and Becca seemed to be in a very, very private conversation. I looked down at Anna's sweet face, turned us so I was facing away from where Becca was, slid my arms around her, and bent down to kiss her.

I didn't kiss her as friend, but as one kisses a lover. She moaned softly as my hand found a breast, I squeezed her a little and continued kissing her warmly. She felt so good to me, but I broke the kiss and eased up on my embrace, and said,

"How was that pretty Anna?"

"Nice Jamie! Very nice! Thank you honey." Then with a knitted brow she added, "Um, Jamie! Do you think you could come over um, like next Friday night? Becky can stay at Becca's with her for the night."

"Not yet Anna, but maybe soon honey. Part of me misses you—misses um, being with you. I have your number, so what if I just promise that it will be soon?"

She brightened a little and said, "Alright, Jamie. I completely understand and will be patient. Y-You don't h-have to stay the night, i-if you don't want to, you could just come over and let me make dinner for you, and we could talk."

There was silence between us for many seconds, as I just enjoyed the familiar feel and smell of her. I have always loved her sweet and floral fragrance. Then she quietly asked,

"Do you miss me Jamie?" I looked down into her pretty face and said softly,

"Yes, Anna ... I do! We've been friends for a long time, it's not something you just turn off!"

The song ended, and we broke our embrace. I saw that the opposite corner was now vacant, and I looked around to find Becca. She appeared talking with a mixed group of guests near the dining room. Tom was in the living room talking again with Kim.

Michael142
Michael142
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