Gillian

CHAPTER ONE

I’ve spent the majority of my life as a “good girl”, I’ve never lied, cheated or stole…well unless you count the time I stole gum from the supermarket…I was seven at the time.

I just turned twenty-seven and I’ve only been with three men. I got married when I was twenty-four, we divorced after only a year. I’ve dated a little since the divorce but nothing very serious.

As good as people think I am, I do have a bad side that no one knows about. It’s something that if anyone knew I thought about they’d probably be shocked. I’m sure it’s something that a lot of women have fantasized about and some lucky women have had the opportunity to fulfill it. After years of thinking and dreaming about it I decided that this year would be the year I made my fantasy a reality!

When I was nineteen I had a boyfriend named William, we had a best friend named Ryan. I’d had a crush on Ryan since I was in grade school but he never seemed to be interested in me “that way”.

I’ve known both Ryan and Will since kindergarten; we grew up together and we were all friends. Once we hit high school Will and I began to date. Will was my first boyfriend and the first man I’d had sex with. He was very conservative and we never experimented.

What got me thinking about this particular fantasy was something that Will said after our freshman year in college. One night while we were on summer break Will and I were hanging out at Ryan’s place (like we did most nights). We were drinking and for some reason Will made a joke about Ryan sleeping in the same bed we were going to be in.

We all laughed and passed out a short time later. Even though it was said in passing, it got me thinking, what if Ryan was in our bed, what would happen? I was very young and naïve about sex, I didn’t know people actually had “threesomes”, I had never heard of such things.

The seed was planted but it didn’t really sink in until Will and I broke up the following year. I was a sophomore in college at the time and my roommate, Julie, was telling me about the time she and her best friend got drunk with her boyfriend and the three of them had sex. I was shocked! I didn’t get into details with her because the thought of having sex with a woman (much less her) wasn’t appealing to me.

I thought back to Ryan and Will and wondered what could have happened if we did share a bed with Ryan. That night I had a dream; I think they are called “wet dreams” all I know is that I’ve thought about it every night since then.

In my dream, I went to visit Ryan to hang out. After a few minutes of small talk one thing lead to another (as they often do) and we were making out in his bedroom. I had never kissed Ryan in real life but in my dream he was a really good kisser! We were kissing and letting our hands roam over each other, I remember he was hard and I had just started to unzip his pants when William walked in.

Ryan and I both jumped up and tried to play it off but the dream Will said, “Keep going, I don’t mind!”

So we started kissing again like it was totally normal. Things were advancing quickly and pretty soon we were undressing each other. My eyes were closed as he removed my bra and panties and he began to massage my breasts.

We lay on the bed and I could feel him kissing my neck and pinching my left nipple. Next thing I felt was him sucking my right nipple, wait a minute...he’s kissing my neck!!!

I opened my eyes and there was Will next to the bed sucking my nipple while Ryan kissed my neck and pinched the other nipple. In my dream I didn’t know how to react so I just relaxed and enjoyed every minute of the two of them touching and kissing me.

I looked down at Will and he looked up at me, he came up and started kissing me and Ryan began kissing his way down to my breasts. Will kissed me more passionately than he ever had in real life while Ryan sucked and bit my nipple. I was so turned on.

Ryan began kissing his way down my belly; he spread my legs and climbed between them while Will continued to kiss me. I felt Ryan begin to touch my pussy with his fingers as he lightly flicked my clitoris with his tongue.

I moaned and Will stopped kissing me, he looked down at Ryan licking my pussy and stood up. I watched as he began to undress, he had a hard-on. He climbed on the bed and straddled my chest. He pressed his cock to my lips and I opened them, he slid his cock in my mouth and I began to suck him. He began to slowly slide his cock in and out of my mouth while Ryan began to slide his tongue in and out of my pussy.

It was only a dream but the feeling of having a man fuck my mouth while another one licked my pussy was so erotic. I felt an orgasm building as Will began to slide his dick in and out of my mouth faster. I was moaning as I began to cum and felt Will begin to cum in my mouth.

Just as my orgasm hit my alarm went off and I woke up shaking with an orgasm. My panties were soaked as I climbed out of bed to get ready for my classes. I was so disappointed that I had to wake up. I would have given anything to be able to have that dream continue.

I had never sucked William’s prick before, in my dream it seemed totally natural to have him in my mouth fucking it with more enthusiasm than he had ever fucked my pussy in real life.

I’ve had the dream several times; if I had a boyfriend the dream would have Ryan and the guy I was dating (even if we weren’t having sex). Ryan has been in all my sexual dreams, even the ones with just one guy. I guess because he’s the one guy I always liked and never went out with.

Ryan, Will and I are still friends; we grew up together and have been there for each other even though Will and I no longer dated. Will is married now and has two great kids, his wife is a sweet girl and we all get along.

Ryan and I are still single; he’s had his share of girlfriends but never stays with them very long. I get a tinge of jealousy when he has a new girlfriend, they are always tall, beautiful, and they look like super models. I on the other hand am short and look nothing like a model, super or otherwise.

I’ve never seen Ryan naked in real life but in my dreams he has a huge dick and I find myself wondering if he does in real life as well. Some times when we are alone my mind drifts to my dreams and I catch myself staring at his crotch hoping to catch a glimpse of his package.

During college Ryan joined the military and moved to Germany, that’s when I met Raymond. Ryan had gotten engaged to a German girl and I thought for sure he’d come back with a pregnant wife.

Raymond was the type of guy a lot of girls were fond of; unfortunately for me he was fond of them as well. He had a hard time with willpower and I found him with other women one too many times. We split up after only a year of marriage.

I spoke to Ryan often while he was in Germany, he never talked about his fiancé and I never asked. We talked about Ray and his exploits and he’d tell me how I should leave him. He was happy for me when I finally moved out and filed for divorce.

Ryan came back from Germany a few months later and he wasn’t with anyone, it turns out his little fiancé had a thing for GI’s and slept with most of the men in his barracks! I have to say I was pretty happy that he was still single being that I was as well.

I don’t know why I want Ryan to stay single, it’s not like we’ve ever fooled around and he’s never given any indication that he likes me as anything but a friend. I still fantasize about him, since I have no boyfriend at the moment Ryan is my only sexual outlet and he’s always in my dreams.

CHAPTER TWO

I vowed that this year would be the year that my fantasy came true; the only problem was I had no idea how to make it come about. I began to go online and read erotica, the problem was that most of the stories involved two women and one man and I wanted mine to be two men and me!

I finally realized it didn’t matter what the male/female equation was, it was a matter of how it happened. Well to be honest most of the stories were so far fetched I couldn’t imagine any of them actually happening to me. I came to the conclusion I’d have to be the master of my own destiny; I would have to figure it out on my own.

About three weeks later Ryan and I had gone out to dinner and a movie, as friends of course. We went to my place afterwards and shared a bottle of wine while we talked. We began reminiscing about our childhood and the goofy things we did. The more we talked the more we drank; pretty soon we were on our second bottle of wine.

I was feeling pretty good at that point and decided I would approach the subject of the night that started this whole fantasy of mine.

“Do you remember our first summer after college?”

“Well we drank a lot that summer, it’s hard to remember much.”

I was deflated; I didn’t want to continue the conversation.

“I do remember one thing, it’s pretty much burned in my memory.” He laughed.

“Oh yeah, what’s that?” I asked with renewed courage.

“I don’t know…it’s kind of stupid. I shouldn’t say anything about it, especially since we’re drinking.”

“No, it’s fine, really.”

“Why are you asking me this anyway? Is there something on your mind Gillian?”

“Yeah, but it’s…well…I mean…”

“Okay, forget it, I’ll tell you!”

I was so relieved!

“It was that one night, I doubt you remember because we were pretty drunk, Will made some lame comment about us sleeping together.”

OH MY GOSH!!! He remembered!!!! I was thrilled!!!!

“Yeah, I remember that too, that’s why I was asking.”

“Seriously?”

“Yes! It was over eight years ago but it was something that got me thinking.”

“About what?”

“About what? About that!” I was on a roll, “About you, me and Will sleeping together, you know having sex!”

“You thought about that? No way! You’re so…conservative!”

“I am? Since when?”

“Well Will always talked about how…shit, I shouldn’t say anything more!”

“Will talked about our sex life with you?”

I was shocked! We were all friends but I assumed our sex life was not a topic of discussion.

“I better go, I’ve had too much wine and I’m sticking my foot in my mouth.”

“No, don’t go! Please, tell me what he said.”

“It’s not important Gillian, you guys aren’t together anymore. Please, just drop it.”

I was getting heated by now, the wine was wearing off the angrier I got. Why was he keeping it from me? How bad could it have been?

“What was it that he said to make you afraid to tell me?”

“You want to know? You really want to know?! FINE! He said you were a great girlfriend but you were a cold fish in bed. He always said you never wanted to try anything new in bed.”

“What a jerk!”

“See, I knew I shouldn’t have said anything. Can we please move on now?”

“No! It’s not true Ryan! I’d always wanted to try new things, all he ever wanted was the same thing. That was why we broke up, he said he didn’t know me, I was too aggressive for him because I wanted to try something my friends had talked about.”

I could feel my cheeks flushing.

“Oh man! I’m sorry Gillian, I didn’t mean for you to get upset.”

“I’m surprised Will talked about our sex life with you at all, why would he even bring it up?”

“It was actually my fault.”

“WHAT??”

“He’d made the comment about us all sleeping together and I brought it up, about how weird that would be, me and him with you. He said there was no way you’d do anything like that because you’re not adventurous in bed.”

I laughed, I mean I really laughed, here I was dreaming about that scenario for years because Will made that comment and he said I wasn’t adventurous.

“Are you okay Gillian?”

I managed to answer him between laughs.

“Yeah, I’m just great!” I broke into laughter again.

“What’s so funny?”

I managed to compose myself so I could tell him.

“If he only knew! He made that comment so many years ago, I’ve thought about it every night since then!”

“You?”

“Yes, me! Boring Gillian thought of a threesome! Can you believe it?”

“I didn’t mean you were boring! I’m just surprised you’d think of something like that. Hell, I can count the number of men you’ve slept with on one hand!”

“Why does it surprise you? I realize I may not be your type but I’m sure I could find two men willing to fuck me!”

“Whoa, what’s with the language? I didn’t mean that! I have no doubt you could find two men willing to sleep with you. Wait a minute, who said you weren’t my type?”

“We’ve known each other since we were kids and you never once looked at me as anything other than your friend.”

“That’s called respect you dork! You were my female friend, it’s not right to drool all over you and make rude comments the way Will used to. That’s not me!”

I didn’t know what to say, I felt really stupid for even bringing up the entire subject now. I wished I could erase the last 20 minutes.

“You knew I had a crush on you since the fifth grade.”

“No I didn’t! You never said anything about it.”

“Yes I did, Will knew! He used to tease me about it all the time.”

“You told Will?”

“I didn’t have to tell him, he figured it out.”

“He couldn’t have known Ryan, he knew I liked you when we were kids. He told me not to bother because you didn’t like me. We were kids, I believed him.”

“What an asshole!” He was laughing, “He told me you only liked me as a friend, he said you didn’t want to hurt my feelings by rejecting me so I shouldn’t bother asking you to be my girlfriend.”

“He is an asshole!” I was laughing now.

“I was so embarrassed when he made the comment about us all sleeping together, he knew I still liked you.”

“All that time?! I can’t believe it! I only went out with Will because I figured I’d never be with you. Damn it! I gave it up to him!”

“I was devastated when you two slept together the first time. He came over the next morning and was gloating; telling me that he had popped your cherry. I almost decked him.”

“He said that?”

“Yeah, he always made crude comments about you, I never told you because I didn’t want to hurt your feelings. I usually ignored him, I didn’t want to hear about it.”

“I wasn’t his first, was I? He said I was but I never believed him.”

“You guys were out of high school when you had sex, of course you weren’t his first!”

“What a jerk! I think I need more wine, how about you?”

“Please!!!”

We opened another bottle and poured two very full glasses.

“Who was your first Ryan?”

“Do we have to discuss this?”

“No, I’m just curious.”

“It was Lacy, the girl I dated my sophomore year.”

“That was when we were in college!”

“I know! I was holding out.”

“Holding out for what?”

“For you.”

I almost spit out my wine!

“For me? Why?”

“I don’t know, I guess I never gave up hope that we’d be together. I gave in to Lacy about a month before you and Will broke up, talk about timing.” He chuckled.

“Was that the reason Will made the comment about us sleeping together? Because you were a virgin?”

“Yup, he could be a real jerk sometimes.”

“Tell me about it!”

We laughed and drank the rest of our wine.

“Can I tell you something Ryan?”

“Depends, is it gonna piss me off?” He smirked.

“I hope not.”

“Go ahead, I guess after everything we’ve discussed tonight it couldn’t hurt, right?”

I smiled, “Well, I still like you, I’ve always liked you and I still want to sleep with you.”

I thought he was going to fall off the sofa!

“What?”

“Oh God! Is it too late to take that back?” I was so embarrassed!

“You still like me? You’re not just drunk, right?”

“I’m not that drunk! I know what I’ve felt for the past twenty years, alcohol can’t change that.”

“I think my head is spinning.”

“There’s something else.”

“There’s more?” He looked startled.

“I want to have a threesome, with you…and well, whoever else we can get.”

“What? Like a girl or a guy?”

“A guy of course!”

“Gillian, you’ve got to be drunk!”

“I’m not! Okay I am but I’m not so drunk that I don’t know what I’m saying.”

“Why me?”

“Because it’s always been you.”

He looked at me and smiled.

“What if I told you I liked you and wanted to be with you, what would you say?”

I blinked several times hoping the saliva would return to my dry mouth before I had to answer.

“You want to be with me?”

“What if I told you I’d love to sleep with you but not be a part of a threesome?”

“I’d be disappointed but I think I’d recover.”

“Would you still want to have a threesome?”

“I think so.”

He poured another glass of wine before he spoke again.

“Well, I’ll make you a deal. Tell me what think, okay?”

“Okay.”

“I can’t be a part of a threesome, I couldn’t share you with some other guy much less watch! I do know two guys that would be more than happy to participate.”

“What about…”

“What about us?”

“Yes!”

“What about us, we’re not a couple, you can do whatever you want before we get together.”

“Before we get together?”

“Yeah! You think I’m going to let my woman fuck two other guys?”

I didn’t know if he was serious so I didn’t say anything.

“Gillian, I want to be with you but I also want you to have what you want and I can’t be a part of it.”

“You’ve always been a part of it.”

“What?”

“In my dreams, you’ve always been the constant factor.”

“Why?”

“Because I’ve always wanted to be with you I guess.”

“Okay, so you’ll have me…will you still want to have a threesome?”

“I don’t know! I’ve fantasized about it since that night but you’ve always been a part of it!”

He sighed and ran his fingers through his hair.

“I don’t want our first time together to have some other guy there!”

“So why do we have to make that our first time?”

“Because when we do sleep together the first time I know I won’t want you to be with anyone else after.”

I wanted him so much! I’d been in love with him since we were kids, I didn’t want to blow my chance to finally be with him!

“I don’t need it, I’d rather have you!”

“I’ll be right back!”

He got up and went into the kitchen. I heard him talking; I assumed he was on his cell phone.

He came in the living room.

“You know my friend Jacob?”

“Yeah.”

“You’ve met his roommate Brian, right?”

“Right.”

“What do you think of them?”

“Huh?”

“Well, they think you’re hot, what do you think of them?”

“They’re okay I guess.”

“You guess?”

“Well Brian is really cute and Jacob is the football player, right?”

“Yeah”

“He’s good looking, nice body.”

“Great! They’ll be here in about thirty minutes.”

“What?”

“Get ready baby, they’ll be here in half an hour!”

“For what?”

“What do you think?!”

“You’re not serious!”

“The hell I’m not! They’re on their way so get ready. I’m leaving and I’ll see you tomorrow! We’re going to lunch.”

“I can’t, I’m not ready!” I sobered up real quick.

“You will be!”

“But what about us??”

“Don’t worry about it, I’ll be okay with it. Have fun; I’ll call you tomorrow so we can go to lunch. Okay?”

“I don’t know about this, I’m starting to freak out!”

“Just relax, they’ll be good to you, I promise. If they hurt you I’ll kill them.”

He smiled and kissed me on the forehead.

“Have a great night Gillian, I’ll see you tomorrow.”

That was it, he grabbed his jacket and left!

CHAPTER THREE

I locked the door after him and ran upstairs to shower. I didn’t know what to wear. I selected a comfortable short cotton dress with short sleeves. I put on a pair of black lace thong panties and a black lace bra. I brushed my teeth and pulled my hair up with a clip.

I had just finished my hair when the doorbell rang. Oh no, they were here! Was this really happening to me? I was terrified; I didn’t want to open the door. Don’t get me wrong, both of these guys are really good looking and the thought of being with them was arousing but I was still scared to death.