Out of My League

Jennifer was a 3rd year law student. I met her in a pseudo running club at school during the Fall semester of my sophomore year. We hit it off instantly, and for the rest of the semester, despite our age gap and school of study, we were always hanging out. We ran, shopped, went out, ate, laughed together -- you name it. I've always been the type to have more guy friends than girl friends, but for whatever reason, Jennifer and I clicked and had a lot of fun together.

For me, she was the type of person I wanted to emulate in so many ways. She was tall, beautiful, funny, and intelligent... and a fantastic runner. She had this way of pushing me beyond of what I thought I could do on our long runs. That said, and I still believe this to be true today -- Jennifer was the most secure person I've ever met. That attribute alone captivated me like none other. She knew who she was, what she wanted to do, and every life-decision passed through those filters...everything.

I, on the other hand, was the exact opposite. And, for the life of me, I can't understand why we she took me under her wing. But she did, and I am forever grateful.

Because we became so close, I started to hang out with her social circle -- all of which were soon-to-be attorneys. As luck would have it, just over eighteen months into my college career my social circles had gotten mundane and routine and I was ripe for a change of scenery. As an undergrad, and one who still couldn't legally get into a bar (I had an id anyway), I knew I was socializing 'up'. That is, I didn't belong in their circle. These people were older and a lot smarter than me, but they were also more mature and had a sense of purpose and direction. Conversely, I was just a sophomore wondering if I was in the right major at the time.

It was a few months after I met Jennifer, that I learned that she was a bi-sexual. I still remember the conversation, over coffee (which she introduced me to), after one of our Saturday morning runs. I never would have guessed it -- not in a million years. I can still remember her laughing at me, causing me to blush, when she told me. I simply didn't believe her. It didn't bother me...at all. I was just surprised. I mean, girls like Jennifer just didn't seem to fit the mold of a bi-sexual (please don't take the wrong way...this is not my feeling, but conjecture as to the perceived norms...either rightly or wrongly). Obviously, my perceptions were forever changed after that moment. While Jennifer was extremely secure in herself, it wasn't something she wore on her sleeve and didn't share with many. Her friends knew it, but it was always on her terms.

So, of course, this took our friendship to a much more intimate and deeper level. And because she opened up about her experiences, my experiences were coaxed out of me as well. Truth be told, she was so damn persuasive and demanded my honesty -- skeletons and all. I completely trusted her. She was the only person, at that time in my life, that I've openly communicated about my sexual history, activities, etc. Many of those stories I've yet to write but suffice it to say that I was a closet slut...And, I was very, very, very good at keeping it in the closet. Like me, her preconceived image of me didn't match what I was telling her. She had me as a 1 guy, maybe 2, but nothing more. It was amazing that we were friends based off completely wrong pre-conceived notions about each other.

I remember having so many unique conversations with her over the next several weeks and months. It felt amazing to be able to share and unload a lot of myself and having someone laugh, love, respect me without, for the most part, judgement. Admittedly, I was extremely curious and had a million questions -- not that I was bi, or anything like that, but more on just how she dated and such. Of course, she, in turn, had questions for me. No stone was left unturned. I found myself seeking her approval, feedback, and input. In some cases I got affirmations, and in others, I got the head tilt what-were-you-thinking look. But always, always -- a laugh, a smile, a tear, cup of coffee or a glass of wine...or four.

I do not consider myself bi-sexual by any means. I date guys and guys only. However, I do consider myself very open, and curious. And, it's possible that I'm easily influenced, but not in a dim-wit sort of way. That said, she knew that I had kissed a girl my freshman year -- mainly as a result of a challenge by a guy that I was into at the time. That is, it was more to get his approval and attention. (Yes, it worked, but that is a different story).

As the semester progressed, so did our friendship. In fact, there were many occasions where she'd stay at my place or me at hers. It started out being just on nights where we went out, but soon thereafter we started shacking more times than not...just because neither of us wanted to be alone. Of course, this made for lots of conversation and pillow talk, which was welcomed. I never felt any pressure. In fact, it was just the opposite. Many of the times, we'd talk about recent dates, or guys who I thought were cute, or whatever. And, in turn, we'd talk about a girl she was kind of seeing/talking to from Atlanta, etc. It was never odd -- just normal girl talk. So, in the normal flow of discourse, I confided in her that I thought two of her friends were attractive, one of which was a really good friend of hers. Let's call him Jeff. I felt like Jeff was into me, but he never asked me out or anything and I just figured the 5-6 year age gap was too much, so I was nervous as to whether I should even tell her that. Like I said, she was persuasive as hell. It seemed to be a very casual comment but she hinted that several of her friends were into me but was never one to play the middle man for them.

Sidebar about Jeff: If I have a guy-type, Jeff was it. He was semi-quiet, incredibly smart, confident, mature, predictable routine, good shape, and handsome but not a in a player-type-vibe way. He didn't know he was handsome, which definitely appealed to me. Sidebar over.

That said, on one drunken night, Jennifer and I kissed. And kissed. And kissed. It was both sexual and non-sexual at the same time. I can't explain it. Surprisingly, it wasn't weird for me the next day -- mostly a testament to just how awesome she was.

It wasn't an every time thing. But it happened again several more times. It was simply kissing. Bonding. It was never about dating. She knew who I was, and vice versa. There was never any pressure. I do remember having make out sessions with her, and in the right moment, her making fun of me in a teasing way. She was one of only a few people that ever called me a slut -- and she was the only one that knew it to be a true statement. I still smile when I think back to some of her little snide comments when we were together, whether it was at a party, a bar, etc. She loved to make me blush. Conversely, she was so secure, nothing seemed to faze her. Frankly, she didn't care.

The subject evening wasn't planned by any means, but the stage had been set for the most amazing experience I've ever had. It would be a night that I would have never signed up for from the outset.

Jennifer and I went to a keg party at one of her friend's house. All of her law school friends were there. I was a bit excited because I remember Jennifer hinting that Jeff would be there and I can still remember my outfit -- a denim mini skirt, black boots, and a long sleeved sweater top that showed a bit of my midriff. Of course, I met Jennifer and friends at her house for pre-party cocktails. She told me I looked amazing, which I still remember to this day. I was used to compliments (that sounds bratty, and I'm sorry), but when they came from Jenn, it felt different -- genuine, free from suspicious motives, and filled me with confidence. We were probably tipsy when we walked up her friend's party, but it is then she laughs and tells me that my outfit looked a bit slutty -- in jest, or course. I just remember it causing me to blush, and she knew it would make me a bit self-conscious. It did, but Jennifer simply giggled and walked through the door to the party. I had no choice but to follow. Bitch.

The party was great and I remember Jennifer continuing to tease me during the party --subtle comments, mostly out of earshot from anyone. At one point, she teasingly even whispered in my ear not to go home with Jeff. It wasn't even on the table, but for some reason this turned me on so much -- maybe it was her approval that I had an affinity for, I don't know. I did not go home with Jeff -- even though we did chat it up quite a bit. I could have, but because of her comment, I didn't send him any signals like that. And, I was just a silly sophomore remember. The party ended and they had someone drive us back to Jennifer's house. On the ride back to her house, I remember Jennifer whispering in my ear as to how proud she was that I didn't go home with Jeff. It was condescending, suggestive, and flirty all in one -- that's just how she was. I knew then that it would be a make out session when we got back to Jennifer's, and I didn't mind. In fact, I was excited about it. In a weird way, shacking with Jennifer prevented me from going home, responding to a late-night booty call or text by someone else, and end up making a 'bad' decision and having to take the 'walk of shame' the next morning before anyone could notice. It would be a walk I'd take many times in college any beyond. Perfect justification, I thought.

That's exactly what happened when we got to her place. This time, though, it was different. She was tipsy too, and she was definitely making a move. I went with it. She offered me a shot but I declined. She took one, though. Wow. Why did it turn me on to see her take a shot, knowing what would follow? It did.

I remember falling on the couch with her as we were making out. I could see the look in her eyes. It was familiar to me, but never one I had gotten from her. In fact, it was the first time I'd ever gotten that look from a girl. She was going to push the envelope and it was like I didn't even have a say in the matter. She was sure this was going to happen. I wouldn't and couldn't say no and she knew it. We only stopped to take my boots off.

There was very little talking, mostly kissing, and lots of moaning. Her hands began to caress my body and while they had the same entitlement as a guy's hands, she also had the familiarity of what she was touching. She reached under my shirt and caressed my breast for the first time. It felt amazing and I let her know that it did -- even if not verbally.

"You didn't even push my hand away," she whispered, kissing my neck as she toyed with my nipple. "It's unbelievable how easy you are," she giggled, playfully.

I bit my lip and blushed, unable to speak. I had no evidence to discredit her assertion. Worse, I didn't want her to stop. And she didn't.

"I told myself that I wasn't going to make a move on you...because I was afraid it would mess things up,' she continued to whisper in between kisses. "But, I'm changing my mind..." she smiled. She kissed me and toyed with me even harder.

"Can we talk about your skirt, Stacy...what did you think would happen when you decided to wear that tonight?" and she never gave me an opportunity to reply, kissing me again. My bra was already pushed up above my breasts and she left it that way. I felt her hand rub the inside of my thigh and open it, causing my skirt to ride higher up my thigh, thus exposing the thin fabric. I started to shake I was so nervous. She traced across my panties with her fingers and commented on how wet I was. "You didn't have any skirts longer, or were you trying to get someone's attention?" she giggled.

By this time, she had already pulled my thong to the side as she caressed my clit with her finger. My mind was wandering, trying to analyze the events, but I offered no objection. I bit my lip as I was formulated my response. Whatever response I was developing, it didn't come fast enough. I looked up at her, nervously and stuck in a dichotomy. I wanted her to like me, but I was also concerned about tomorrow. I wanted her to be happy, and I didn't mind being the person that made her happy. In a weird way, I owed her something. And, it did feel good -- physically, and emotionally.

Side bar: She knew that I orgasm easily from information that I'd told her in our talks. This has always been a 'fault' of mine and the reason for many lowered inhibitions. Side bar over.

"I love your panties...so pretty," she smiled. Jennifer slid a finger inside of me and she kissed me passionately. It wasn't long before I was gyrating my hips to meet her hand, as I looked up at her as I tried to usher in my orgasm, welcoming it and the consequences it would bring. I wanted it and needed it. More importantly, and less selfishly, I wanted her to have the satisfaction and confidence boost from doing it to me.

"Someone is being naughty," she giggled, in her condescending tone. She was drunk, and in charge. I was compliant, and willing. She bridged up on her elbow and looked down at me as she began to move her hand inside of me faster. After a few sexually charged minutes, it was in sight and she knew it. My mouth became dry, my breathing changed and I looked up at her, as if begging her to make it happen.

It started in my toes. Soon the waves of orgasm enveloped me and I began to cling to her, dependent on her, thanking her. I should have been embarrassed and ashamed of my uncontrollable noises, whimpers and trembling, but didn't have the wherewithal to even process. Powerless. She just rested her hand there, letting my body dictate the final movements, rhythm, and pressure. My hips lifted and lowered, my back arched, legs spread before sinking into the depths of the sofa. I clung to her arm as I saw her smile down at me. I lay there with my skirt around my hips, my thong around my thighs, my sweater lifted, bra still intact, but grossly askew. "I'm so embarrassed, Jenn..." I uttered, but smiling. I needed her affirmation in that moment. She giggled and got up from the couch, "I know you are processing what this means, and what tomorrow looks like...don't. Just stop. Come with me."

She took my hand and led me to her bedroom. It was there that we kissed again and she began undressing me. "Just relax...just for fun. Doesn't change anything, I promise. Have fun." I smiled, as did she. Everything seemed okay in that moment. I had never been with another woman, but this was happening. I wanted it to happen...for her. And for me, too.

"Don't be nervous. It will come naturally," she smiled before she kissed me. She undressed herself as I stood there, timid, but willing. I liked the kissing and that was my go-to when I didn't know what to do or say. We then got into bed with her on her back and I at her side, my leg draped across hers. I began to kiss her neck, worshiping her it seemed. She was responsible for my orgasm and I wanted to return the favor tenfold. I wanted to take care of her, to please her -- familiar emotions, different gender. Her body was simply beautiful. She smelled amazing, felt amazing. She would deny it, but truthfully, every asset she had...was better than any asset that I had. I stared at it, caressing it with my hand, but scared to touch any of her erogenous zones -- not because they were off limits, but rather because they were like mine, but not mine.

She guided me through the heavy make out session and encouraged me to go lower. I got the hint and without any physical hesitation kissed my way down her tummy then hips, and eventually positioned myself between her legs. She looked down at me, and smiled. "It's like you are losing your virginity all over again isn't it?" she smiled. I smiled back, not having a clue how this would go. I just wanted to make her happy. She deserved it -- whatever it was, in that moment.

Nervously, I tasted her for the first time as I pressed my tongue against her perfectly trimmed pussy. I read her body language -- the way her eyes closed, the way her lips moved, the way her shoulders relaxed, and mostly the sounds she made. I licked slowly, carefully, and softly as I glanced at her breathing, or lack thereof. I watched her move, which was the most amazing part for me -- that connection. Being responsible. My confidence increased and I went faster; softly, then hard. All the things I wanted to tell a guy, but didn't have the nerve, I was now doing them...to her. If she were like me, she would appreciate it. My observations as I looked up at her confirmed that notion and it wasn't long until I felt her hands in my hair. She clinched, but not in a painful way. It was her way of showing positive reinforcement. I held steady and licked her clit rapidly until she came -- not pulling off until she collapsed back onto the bed. It was amazing, watching her body writhe under me like that. It was such a joy knowing that I was the person that caused it. I'll never forget the emotional connection I received from seeing her open her eyes and look down at me. I was still kissing her prize when she pulled me up to her and immediately began to kiss me harder. It was like a switch had been flipped inside of her.

"I wish I could fuck you right now," she whispered and she rolled me over on my back.

"I have never seen you this way -- you are so beautiful," I replied. My voice was barely audible, taking it all in. It was never discussed -- just happened. There were no regrets and no objections, to be clear.

"You would do anything I wanted you to right now, wouldn't you? You are adorable. I totally can see why your boyfriends keep texting you, long after you've moved on." She teased, as she began to toy with me all over again.

"You make me blush...it's not that...I'm just...I don't know...I need to be...," I fumbled.

"Did you like that? I know you aren't like me in that way...but I really appreciate you indulging me tonight. I promise you, this wasn't planned...I wouldn't lead you on like that"

"I know...I like making you happy...it's different, but...I enjoyed it," I smile.

"You aren't mad at me?"

"No...not at all. Promise"

"Thank you."

I smiled back, "thank you."

"I am on cloud nine right now...I don't want to go to bed. Do a shot with me! Right now," she beamed and leaned down to kiss me. I hadn't a choice as she walked out of the room. I remember walking towards the kitchen, naked and thinking, what just happened. I wasn't complaining. It was just out of left field.

I didn't need another shot. Neither did she. But, that's what happened. We giggled, and kissed as we stood there in the dark kitchen.

"You aren't ready to go to sleep are you?" she asked me. I shook my head no. It wasn't what she wanted, and I knew that. I could feel the effects of the shot almost immediately -- the warmth in my toes, and fingers. Combined with the euphoria of being with her and feeling so happy in the moment of bonding, it would be a recipe for disaster. It would be weird the next day, but neither of us was thinking past that moment.

"I knew you told me you could be a little bit slutty, but I basically had your panties off in no time," she teased me.

"Whatever. I don't like you...at all. It's not a fair comparison at all and you know it. I would never act so fast like that with a guy...you can't blame me for that," I giggled.

"Ummm...SAE Mark says hello. And Hunter. Shall I continue?" she laughs. I blush.

"Those were different...I hate you," I giggle. We both do -- still standing there in the kitchen...naked.

"Does it bother you that you don't have a guy here to fuck you right now?" she continued. She poured us another shot and I followed her lead. By way of our girl talk, Jennifer knew that my weakest moments were post orgasm and I had confessed to her that I couldn't think of a time in which I had an orgasm, and then denied the guy sex. Again, it was the ultimate inhibition eliminator as time and time again, I ultimately allowed instant gratification to win out. There was a method behind her questioning and suggestions but I was too naive to recognize it at the time.