TAMMY and JENNY 1

Sometimes I write a story for me.

This is a fictional story based on real, true experiences with the exception of the major surprise that you will know when you know. No spoilers or hints, just a fictionalized gathering of actual experiences and situations put together into one story. Some of the events really happened, same with situations and conversations, but the surprise, the shock, that's just me writing what I write best, emotion, romance and chaos. Let me know what you think, this is unlike anything else I have ever written and I hope you like it.

Character names have been changed or created to both protect those involved or mentioned and to fit the character. No offense to anyone is intended and this will make sense to you as you read, and the parts unfold. I value all life, people, thoughts, lifestyles and choices.

Any people, places, names, products or events mentioned are done so without permission or endorsement, this is a work of fiction.

My name is John, I am 24 years old, stand 5' 11" with short black hair, hazel eyes, a fit, athletic frame, and I work as an events coordinator slash public relations agent for a major company in Northern Virginia. I have been in my job for three years as I finished college. I started as an intern, became part time in ‘events' then was offered the combination ‘PR' and ‘EC' position last year. As such I have long days, travel sometimes, and don't have much of a personal life. The pay is GREAT, the benefits amazing, and I work with great people. My family is wealthy, and that's not a plot point. The truth is even without my good job and great pay, I have had a good life.

I have been single for almost a year. Occasionally a couple girls... women... from the office have spent the night, not at the same time, but it's casual and sporadic. In reality, besides my workload and crazy hours, the reason I'm single is my best friend and roommate Tammy. 1000 words and 30 pictures couldn't do Tammy justice. A cheerleader from the age of 8 through high school and college, even now she cheers for a certain football team nearby in BALTIMORE during football season and for a basketball team in DC the rest of the time. You know, the RAVENS and the WIZARDS? In her spare time between the two sports, she does personal training for rich and wealthy clients. Tammy is 25, 5' 10", has long, dark hair, light blue eyes, an absolutely fit, toned, tan body, and is maybe the hottest and most beautiful woman I have ever met or known. We met in college and while I wouldn't call us best friends, we have a closeness that few will ever achieve. But we've never been together and probably never will be.

The reason is simple. Tammy is gay, lesbian, whatever.

Not over the top and not secretive. Honestly if you didn't ask her or know her, you might never guess. Tammy just prefers women and I should know. I've tried everything I can think of to sleep with her. We've been roommates for almost 3 years, and while she doesn't seem to have or want a steady girlfriend, she also doesn't want a boyfriend. We can talk about anything, she gives great advice, and she's my yin to her yang, my tic to her tac. Sorry, it seemed clever in my head. At first, Tammy had an ironclad, don't touch rule that was simple. Hugs were okay, brushing by each other was fine, but nothing sexual or romantic. I have never pushed, never pressed, but as she let her guard down and trusted me, opened up, I knew she didn't want a man because they were men. By nature men lie, cheat, break promises, have wandering eyes, and take women for granted.

She's not lying or wrong.

Over time, a touch happened, mutual staring, flirting, a kiss here and there, we've even cuddled on the couch watching a movie, but anytime I would ask Tammy to sleep with me she would shake her head and say "No. Sorry." Being a guy, an avid consumer of porn, and having read a fair amount of romantic and erotic stories, I think I know when a woman is interested. Hints, clues and signs pointed to Tammy thawing the ice and maybe allowing something to happen. My guess is if she did, it would have to be sex, just sex, no romance, feelings or commitment. I asked her one night a few weeks ago when we were having dinner alone. No girlfriend, date or friend from work for me, and Tammy was alone as well. I asked "Hypothetically, if something were to happen, and I would be really happy if it did, if I promised not to have expectations or change our friendship, do you ever see that happening?" Tammy stared at me, chewed a piece of steak, sipped her wine, then flirted "So, you finally fuck me, your life goal is reached, and then you just turn that part of your brain off and that's that?"

Wow.

I laughed, "It's a good thing you don't think you're all that." Tammy smiled then said "And yet you're the one chasing me like I robbed a bank." We ate quietly until I asked "Have I ever once insulted or offended you? Made you feel less of a person?" Tammy gasped as I stood, then said "I'm sorry if I said something that offended you Tammy. I value our friendship." She just stared at me as I scraped my plate, put it in the dishwasher, then went to bed early. Four days later of somewhat indifference between us, mostly because of work schedules, Tammy came into my bedroom in the tightest spandex shorts and top I have ever seen or imagined, and she asked "Can we talk?" I held my breath and nodded as Tammy said "I don't like where this has gone and I apologize. Saying no and being a bitch are not the same thing, so let me ask you a question. Is once enough? If something happened between us, is once enough? What do you want from me John? What do you want from me that I can give you and not compromise what I think and how I feel?"

I exhaled, forgave Tammy, then stepped closer and we kissed. It was actually our first real kiss ever. We have kissed on the cheek now and then, even kissed on the lips a few times when one of us left for a trip or came back from one. This was our first open mouth tongue kiss and it was nice. Tammy held me, her body relaxed, and we kissed for what seemed like several minutes. When we parted she said "I would like it if we didn't talk about it and for lack of better phrasing, let's see what happens." I said "You should know by now Tammy that I love you and I certainly respect you." Tammy touched my face then said "Then when we're alone, let things happen but please do not push me, rush me or talk this to death and if..." Tammy exhaled, her eyes were laser focused on mine, and she continued "When it happens, please be respectful if I pull away afterwards and decide once was enough." I said "Thank you" and Tammy blinked, tilted her head, blushed, then said "Not... not the response I expected" and she put her hand behind my neck and we kissed a short romantic kiss.

Needless to say, I went to bed in a good mood.

I don't know what I was expecting. I know what I hoped. In truth, I didn't get either. Instead it became a game of seduction that I never expected. The next three evenings the flirting was turned up to 10, we were kissing, Tammy even let me feel her up through her cheer uniform which I think she intentionally didn't change from. Then on Friday at work, a wild card got tossed on the table that I never expected. I got called into the senior VP's office and he wasted no time saying "So you're going on a cruise."

What?

He said "Take your wife, uh, are you married?" I shook my head and he said "Well, take your girlfriend or boyfriend or whatever your preference is and..." I interrupted, "Sir, I'm straight." He stared at me then said "I apologize. This isn't an HR thing is it? I meant no offense John." I said "It's fine. Why a cruise and why me?" The VP said "It's your turn. Collins went on the Super Bowl Vegas jaunt and Michelle just got back from the NASCAR thing. Kyle is going to WRESTLEMANIA and you know Melanie is going wherever TAYLOR goes." I sighed "I would love to go on a cruise sir but I'm not seeing anyone right now." He laughed "Listen, if you can't hook up on a cruise, there's something wrong with you. My wife loves it when we go on a cruise. For 5 days or 7 or whatever we play a little game where we take off our rings and pretend we don't know each other."

Wow, talk about way too much information.

He laughed "Anyways, it's some kind of Country music themed thing, so for the most part you just enjoy the cruise, all expenses paid including the airfare both ways, hotel before and after, all meals, drinks and shows. The only thing you have to pay for is incidentals and souvenirs and as you know, you have a generous expense account."

So no down side, other than being single and having no one to take?

He said "I'll have Jenny send you the details and get with you to book everything. It's in two weeks. Have fun" and then he waved as if to dismiss me.

Two weeks?

I was at my desk in my small office trying to focus, trying to concentrate when I called Tammy. She was out of breath and said "Hey babe, I'm at practice. What's up? You never call me." I asked "Babe?" Tammy said "In or out John, you pick. I'll wait." I exhaled "In I hope." Tammy laughed "We'll see. So what's up?" I said "I need to see you." Tammy exhaled "Well, you wouldn't call unless it was important but we agreed to work up to it, so that can't be it. Uhmm..." I interrupted "Tammy, I need to see you, it's important, and if I wanted to make a move on you, it would be at home, in private as you asked and deserve." Tammy exhaled "See? It's already getting complicated" and she hung up. I was staring at my phone when she texted "I'm going to shower and see you in about 40." I texted "I love you" and Tammy called "John, this is not like you, what's wrong?" I asked "Please? I would never bother you unless..." Tammy said "I'll skip the shower. 30 minutes, 25 tops, and I love you too."

A cruise? In two weeks? By myself?

Jenny came into my small office and made everything better. Jenny is in her late 20's, 5' 10" with long blonde hair, blue eyes, a body that should be on ONLY FANS, and was born to flirt. Our interactions have been flirty, but I think she's married. Today she was barely wearing a short blue skirt that started or ended mid thigh and showed off all of her perfect legs. Her crisp white blouse was unbuttoned past her light blue bra that struggled to contain her large breasts and all I could do was sigh. Jenny stepped closer so that she was inches away from me sitting in my chair behind my desk and asked "When are you going to make good on all the staring and flirting?" Huh? I asked "Aren't you married?" Jenny's eyes sparkled "No, I'm waiting for the right guy."

MAKE SURE YOU REMEMBER THIS CONVERSATION.

I stared at the door to my small office, Jenny followed my eyes, blushed, then asked quietly "Should I close it?" I couldn't think. My brain was literally stalled, maybe frozen. Jenny smiled, "I'll just close it." She did, then nudged and pushed me so that she slipped past my legs and knees, wriggled up onto my desk facing me and essentially between my legs, and now I knew her panties matched her bra. I gasped "Dear God." Jenny said "John, we can flirt in circles forever or you can ask me out. I think 5 months is long enough." I gasped "Five months?" Jenny said "I think. Maybe 6? I've been single since just after Halloween and you can pretend all you want, we've been flirting but going nowhere." I swallowed then breathed "But you're..." Jenny exhaled and the light went out of her eyes as she sagged and asked "I'm what? Too hot? Too pretty? Unattainable? Forget it. Come see me when you want to discuss your itinerary."

I reached out and caught Jenny's wrist, she stopped where she stood, and stared at me. I stood and asked "Will you go out with me?" Jenny stared at me for a long moment and then Tammy came in and said "Oh sorry, I didn't mean to interrupt." Jenny's face and eyes got sad, she shook her head, then said "Come see me when you want to discuss your itinerary." I asked "Jenny, please?" She shook her head and said "Just come see me." She left, Tammy came in, shut my door, then said "So spill. What was that?" Now I was conflicted. Tammy was my closest friend, my roommate of several years, and potentially, at least once, a lover. At least I hope. Jenny is one of the hottest women I know, seemed to be into me, and before I seemingly blew it, was lined up to have sex with me, and probably not just once.

Now what?

Tammy was in black leggings, a NBA logo t-shirt, and her hair was back in a ponytail. For someone who was sporty by nature, she just exuded it at that moment. I sighed and asked "Can I hold you? Will you hold me?" Tammy set her keys and phone on my desk and held me when I stood. I sighed when she kissed my neck softly and asked "What's wrong? I've never seen you like this." I eased back from the embrace and kissed Tammy. She relaxed and it turned into a warm, passionate kiss that lasted. When we eased apart, Tammy said "I'm not trying to break the mood John. Tell me what's going on and then we can kiss, okay?" I nodded, let go of Tammy, then sat in my chair. Like Jenny had done, Tammy sat on my desk facing me, her legs between mine, the only difference was Tammy had leggings on and not a skirt. I must have been staring at her crotch because Tammy blushed and said "Wow. I have never seen you like this. What happened?"

You know that saying ‘You can only die once'?

I stood, Tammy must have sensed my needs, and she tilted her head so that we kissed. I was getting hard, there was no way to hide it, and midway through the kiss I felt Tammy's hand on my bulge and she asked "Is this what you want? Do you need this John?" I pulled at her t-shirt but Tammy pushed me back, away, then slid off my desk to go lock my office door. She was staring at me and asked "If I promise this will happen... tonight... will you wait until you get home?" I nodded and then said "I have to go on a cruise." Tammy adjusted her t-shirt, then said "Thanks for getting me excited, now my panties are wet." I smiled and she exhaled then said "You only get one warning John. If we do this, it's just a thing and it ends when you get clingy. I do not want a relationship, especially with you, because we have too much to lose in a breakup." I said "I will treat you like the lady you are, the friend I value, and I would never do anything to hurt you."

Tammy blinked, then with her eyes locked on mine she smiled, exhaled, then said "Well in that case." She moved closer and started working at my belt. There is no doubt we were about to do it when there was a knock on my office door and then Jenny shouted "John? Are you in there?" Tammy let go of my belt, nodded, then stepped a good ways away from me. I had my belt done, my clothes fixed, and opened the door to Jenny who said "I'm sorry for before. I have a thing with men thinking I'm too good for them. I'm no better than anyone else. Yes, I'll go out with you."

Then she spotted Tammy looking at my degree and other awards on the wall.

Jenny blushed and said "Oh, I... I didn't know your friend was still here." I said "Jenny, this is my friend and roommate Tammy." Tammy was all smiles with her hand extended to Jenny who was blinking rapidly and repeating "Roommate? Roommate? She's your roommate?" Tammy dropped her hand and said "I came to console him. Apparently he has to go on a cruise with short notice and has to go alone. He's not dating anyone you know?" Jenny seemed confused "You're not? I thought we were... uh..." Tammy said "Hey I know, Jenny you should go with him. What a great way to start a relationship on a cruise away from work and all the stress." Jenny blinked then asked me "You want me to go with you?"

This was odd.

What happened to the strong, sure, bold Jenny from an hour ago?

I'm not sure why Tammy poured gasoline on the situation when she told Jenny "I cheer for the RAVENS and the WIZARDS plus do personal training. There's no way I could go with John and besides, we're not like that." Jenny faced me and asked "You're not?" I shook my head and asked "What's wrong Jenny? An hour ago you were bold and now you seem..." Tammy said "Shy." Jenny sat in the chair in front of my desk, I got another flash of light blue panty, and she sighed "I usually am." Tammy was smiling at me so I knew she saw Jenny's panties. I mean, her skirt was pretty short. Tammy said "Well, I have a date tonight and she might spend the night, so it was great meeting you." Jenny blinked and asked "She?" Tammy laughed "Yeah, I prefer girls" and then waved at me and left. Jenny was still blushing and blinking when I crouched in front of her, held her hand, and asked "Are you alright?"

With a deep inhale and a long exhale, Jenny asked "So you're not sleeping with her?" I told the complete truth when I said "Jenny, I have not slept with Tammy." She smiled then asked "So, you want me to go on the cruise with you?" I asked "Can you? Is that possible?" Jenny laughed "Do you know who makes most of Robert's decisions for him? Who arranges his meetings and schedule? Who approves most of his memos?" I asked "Can we talk about the itinerary over dinner? What time can you leave?" Jenny said "Yes and maybe in an hour. I have to input the notes from the VP meeting and then we could go." Jenny stood, we embraced, she was warm and smelled great. Sort of a vanilla cotton candy scent. Our eyes met, Jenny pressed her lips to mine, and then we kissed. A soft kiss at first, then she parted her lips and it became romantic and lasted a minute, maybe two.

I was happy and all the voices were quiet.

Life was good.

Jenny put her lips to my ear and said "I trust you when I tell you this. I have been dressing like this to get your attention for weeks. I have turned down phone numbers, dates and offers hoping you would notice me." I said "I notice you Jenny. I just hope that I can contain the excitement that I feel when I see you." Jenny was practically purring when she said "If dinner goes well, if whatever we do tomorrow is good, you won't have to." I blinked "So tomorrow night?" Jenny was blushing when she purred "I'll give you a strong maybe. It depends on dinner." We kissed softly, then Jenny smiled "See you in an hour?" I nodded then Jenny asked "Uh, are you coming to my desk or should I come get you?" I smiled and then Jenny said "Wow. Ok, see you in an hour or so." As soon as Jenny left I called Tammy who laughed "What happened? How did it go?" I asked "How much do you love me?" Tammy said "That's not fair. Why would you ask me that? Is this about the cruise? John, if I didn't have games to cheer and clients scheduled, I would go with you baby, but this was way too sudden."

My mind was blown.

First ‘babe' and now ‘baby'?

What happened to no feelings, no relationship?

I said "I was going to ask you to buy some flowers and get them here to me without Jenny knowing." Tammy let out a long sigh, then said "Don't interrupt me, just listen." I did and Tammy said "This is not a bad, worry yourself to death ‘we need to talk', but babe, we need to talk." I said "Anytime you ask. You come first and I think you realize that." Tammy sighed "What kind of flowers? Cheering for the WIZARDS holds some weight around here?" I told her, then she said "I hope you know I love you" and hung up on me.

What happened to no feelings?

I finished a report, joined a short video meeting, and was shutting down my computer when Tammy slipped into my office. She had flowers in a really nice vase and had changed clothes into a cute, knee length, sleeveless blue dress that fit her perfect body like a glove. I couldn't put my finger on it, but something was off. Tammy flicked the lock, set the vase on my desk, then stared into my eyes when she reached under her dress, worked at, then slipped her panties down and off. I was stunned, and even more so when she put them in my hand and said "No more games." I worked furiously at my belt, pants and underwear, and was getting hard in a hurry. Tammy said "Something about you bringing that knockout blonde to the party drives me insane with jealousy. Jealousy I never knew existed. Fuck me."

WOW!

Tammy was leaning against my desk, lifted her dress so I could see her slit and lips were wet and she was shaved bare. I was looking at her large chest in the dress and she said "You have my word you will see me naked and can use my body like a playground." I stepped closer and just pushed my cock deep into Tammy's tight pussy. She let out a combination grunt and moan as her hands held me and I slid slowly into her wet, tight body. I had just started stroking when Tammy purred in my ear "I want to modify the terms of our relationship." I huffed and drove deep into Tammy who panted "Yeah... ohhh... we can fuck until... oh yeah..." and then she held on because either she was pent up or something about this secret office fuck drove her wild.

Maybe both.

Tammy's body tensed, she sucked in a whole lot of oxygen, and then she bit into my shoulder as she shook and vibrated through one Hell of an orgasm. I can usually last but as I drove into Tammy, the one woman I have prayed to fuck, she gathered herself post climax and growled into my ear, "You cum in me right fucking now."

I drove deep, hard and fast. I could feel the pressure building, and then when Tammy nibbled my ear I exploded deep inside her and kept pumping until I was sure nothing was left. We held each other, cooled down, calmed down, then Tammy said "I changed my mind and when I say that I mean you changed my mind. You might be the only guy to ever fuck me, but until I meet someone and get serious, I want you to keep doing it, Jenny or not." We kissed and then I said "Thank you." Tammy laughed "That's twice. Why are you thanking me?" I said "Because when someone gives you an awesome, incredible gift, you say thank you." Tammy kissed me furiously until she pushed at me, we separated, and used a cloth she handed me to clean up. I didn't ask where she got it. Clearly she came here to have sex with me. Changing into a dress before coming, handing me her panties, saying "FUCK ME" are all pretty good indicators.

We were dressed and Tammy asked "Can we talk?" I nodded and she said "So this changes nothing and everything. You're my best friend, my roommate, and now my lover. The only guy I have ever been with and probably the only one I ever will be." I said "I love you Tammy and will never, ever hurt you, but if you want no feelings or complications, then help me with Jenny. I can't figure her out." Tammy blinked, then said "I will, of course, but what gives you pause? What concerns you?" I said "Maybe it was work mode and depression, maybe I was hung up on wanting you, but other than thinking she was hot, I never paid attention to Jenny. I just assumed she was married or with someone." Tammy said "I understand that more than you realize. Go ahead." I said "So today she sort of gave me the full court press. You saw that slutty skirt and blouse." Tammy was smiling and she said "That panty flash wasn't accidental. Trust me, I know something about short skirts and how to sit down carefully." I grinned and Tammy said "Focus. You'll be scoring on that goal for a while now. Back to your point."

I asked "What changed?" Tammy said "If I'm honest, and I always am, something about you going from undivided attention to indifference combined with desire and excitement. I think you're hot and sexy and now I know you can fuck, I just don't like drama. I get that from the other girls, on both teams." I said "Makes sense. So for some reason today Jenny was all about me and practically threw herself at me then one sight of you and she balked." Tammy was thinking then said "I know the rest. Well, my guess is she wanted your attention and when nothing else worked, she used her body and looks. It's what I do." I froze and Tammy blushed then said "Don't. That powderkeg only explodes. We're where we are, where you wanted to be, don't pull at threads." I said "Still." Tammy said "In life there are wants, needs and what we have. I wanted you, I don't need you, and now as long as things don't get complicated, I have you. Please keep your promise and don't overthink it?"

Jenny knocked, then asked "John? How does this door keep getting locked?" Tammy inhaled and then asked "Do you trust me?" I nodded and then she said "No matter what I'm about to do, I love you." I unlocked the door and Jenny said "I don't understand how your door keeps... oh... hi Tammy." Tammy smiled at Jenny then asked "Are we clear? Do we understand each other?" I said "I'm not sure, can you explain it again?" Jenny moved closer to hold me, and I held her back as Tammy narrowed her eyes and said "I have a friend spending the night and normally I don't care if you stare at, flirt with or sneak peeks at my girlfriends, but this one's really shy." Jenny scolded me "John" and I smiled then said "Sorry." She rubbed my back and asked "So you need some privacy tonight?"

Man, Tammy was a genius.

She said more to Jenny than me "I just need him to crash somewhere or stay in a hotel, just this one time, so that..." Jenny said "He can stay with me" then she looked at me and said "You can spend the night with me. We'll figure it out." Tammy was blinking when Jenny pulled at my shirt, adjusted my belt, then asked "Do you want to take my car or your truck? We can just leave a vehicle here tonight." Tammy leaned into the lie and asked "Could you get what you need so that I'm alone when she gets there?" Jenny said "You know what? Let's get your stuff and I'll cook or we can order something." Tammy said "Thank you" but Jenny laughed and said "No problem. I said he could spend the night, but what he doesn't know is I have a really nice sofa and lots of pillows." Tammy smiled and said "I like you." Jenny tensed against me, inhaled, blushed, then asked "Uh... you like me or you like me?" Tammy flirted "I don't know yet."

What just happened?

Tammy left, Jenny almost fainted when she saw the flowers, then she blushed bright red and purred in my ear, "Maybe if dinner goes well, you won't be on the couch." I smiled and Jenny flirted with her eyes then said "Let's go. I need to talk to you about something in the truck and tomorrow we can go over our itinerary." I said "We're off tomorrow" and Jenny said "I know. Play your cards right and you can spend the entire weekend with me." I smiled and we kissed softly then Jenny said "But I need to book our stuff before it's too late. Two weeks is not a lot of time." In the elevator, Jenny held my hand proudly and said "Robert didn't even blink when I told him I was going with you on the cruise." I asked "Really?" Jenny laughed "I have his files all passworded. Call it job security." I laughed, then held the door to my truck open so Jenny could get in. Besides getting a good look at her panites and inner thighs, Jenny smiled into my eyes and said "Behave, that's for after dinner." I blinked and she flirted "You didn't really think I was going to make you sleep on the couch did you?" I smiled.

At my apartment, Jenny looked around and seemed happy as I gathered things and she reminded me to pack for three days, until Monday. I was getting my razor and toothbrush when I asked Jenny "How long have you wanted us to go out? For me it's since the conference." Jenny inhaled so much I was worried she would pass out. She gasped "The con... the conference? Last August?" I nodded and she seemed dizzy, sat on my bed, then fell back to lie down and closed her eyes. She was silent while I packed and stole glances at her. Her short skirt rode up and I could see all of her panties. She didn't seem to care. I set my bag down, knelt between Jenny's legs, and she opened her eyes to stare at me. As I touched then held her legs she glanced at my open door and breathed "Not here. I'm not saying no, I'm saying not here. Please?" I nodded, leaned in to kiss her moist panties, and I could not only see but smell Jenny's excitement.

She got off the bed, adjusted her skirt while blushing, then asked "Since August? I didn't think you liked me. Or at least figured you didn't notice me." I shook my head and said "You don't know what it's like being a guy, never knowing what women think. You're so beautiful Jenny, your body is like model perfect, your laugh is intoxicating and I just..."

Jenny gasped "MARRY ME" then kissed me furiously.

She was all over me and then it hit me. She just wanted to be wanted. I held her until she calmed down and nibbled my ear to purr "Let's go. I want to take a shower before dinner." I smiled at Jenny who said "When we get to the truck I'm ordering food and then we're taking a long hot shower together." I pushed my luck and whispered to Jenny "Wouldn't it be smarter to take a shower after I have my way with you?"

Just like I guessed, Jenny exploded all over me with kisses and touching, rubbing and grabbing me. It took serious effort to calm her down and for the first time in my life I knew for absolute certain that I was about to get laid. I picked up my backpack, held Jenny's hand, and she was so happy and excited she seemed to be vibrating. We were at the front door, I was glancing around to be sure that I didn't forget anything, and then it hit me...

Did Jenny say "Marry me?"

... to be continued.

NEXT PART - Getting to know Jenny, sneaking around with Tammy, and cruise prep.