My First Time with Another Woman

I've always enjoyed sex. I've never been shy about my body. And I can be quite adventurous sexually. I fall short of being a total slut, but not nearly a "good" girl either. But I had never had an interest in being with another woman until recently.

I am almost 27, single and attractive. Not drop dead gorgeous or anything like that, but I have a natural girl-next-door look and I have a shapely body that I work hard to keep. And I can be very sexy when I want to be and I have been known to turn quite a few heads. To give you a mental picture, I am 5'9, about 125 lbs., I have nice firm 34C breasts, long straight blonde hair and brown eyes.

Almost a year ago, I broke up with a long time boyfriend of 7 years. It was bound to happen. In our 7 years together starting in college, we broke up 6 times and we saw countless people in between our "breaks." Sean was a jerk but he could be so romantic too and he was a hunk. And when we were together, he could rock my world. This time, however, we were done for good. And I hadn't seen anyone for more than 2 dates since. I've had some fun encounters, but nothing that rocked my world. That is, until I met her.

Since the break up with Sean, I've been really horny. I even began going into chat rooms and having cyber sex... something I never did before. I found a few wife sharing sites where women and couples posted and swapped pictures of themselves. I even took some pictures of myself... but I haven't had the nerve to post them... yet. And I got curious about what it would be like to be with another woman.

I first saw her as I got on the train to head home after work. I recently moved out of NY City to an apartment within walking distance of the commuter train station about 45 minutes north of NY City. The train was full and I was standing in the well of the train by the door (there is no chivalry on the commuter train). She took the spot against the wall across from me. We looked at each other and shrugged and smiled, but no words were exchanged. Nor would there be for the rest of the ride. But I couldn't resist looking up from my book throughout the ride to sneek glances at her.

She was quite a bit shorter than I, about 5'4. I couldn't make out just how nice a body she had as she was wearing black pants and long jacket, but she was clearly petite. Her shoulder length auburn hair framed her adorable fresh, freckled face and her deep dark brown eyes were enchanting. She looked young, definitely in her twenties and I couldn't believe how attracted I was to her.

I couldn't keep my mind on my book. My mind drifted to thinking how I would love to be seduced by her. I began to devise ways to introduce myself and invite her for some wine and maybe dinner at my apartment. No! I could never do that... how mortifying if she had no interest. How do you meet women? My mind was racing. I was a puddle of emotion and I felt my panties getting damp. I felt very sexy that day in a short, black sexy skirt that showed off my shape and a white blouse that showed just enough cleavage to be sexy while still appropriate for the office (albeit, a creative one as I work in advertising). I had no hose that day (or most days) and was wearing black sling back heels.

Before I could devise away to start a conversation with her we arrived at the first station stop and enough people got off to open up several seats. She grabbed her bags and found a seat. I remained standing as I had been too deep in my daydream to pay attention and the empty seats were taken. Besides. it afforded me a nice view of her still.

I continued to fantasize about meeting her. I had convinced myself that she definitely liked girls and certainly, I would be very attractive to her. Then, we reached my stop. She didn't move. Neither did I. I couldn't believe it. Why didn't I get off? I couldn't just get off and let her slip away. But now what was I going to do? What would I do when we get to her stop? I had no clue, but stayed on the train as we made stop after stop. She didn't move and I was getting further and further from home. And more and more excited. The butterflies in my stomach were becoming unbearable. I was trembling. I finally took a seat where I could keep an eye on her.

Finally, we reach the last station stop. The end of the line and she got off the train. I held back slightly to follow and see where she would go. Would there be someone there to pick her up? Please no, I thought, that would be devastating. I breathed a sigh of relief as I watched her get into her car in the parking lot. A two seater.

I suddenly came to the realization that I was now stranded! I looked around and saw that the last taxi was leaving with a passenger. I had no idea when the next southbound train would come. I was flustered now and must have looked more than a bit confused and upset because all of a sudden a car pulled up in front of me and the window rolled down. It was her!

She leaned across the passenger seat and called through the window, "Hi, you look a little lost, do you need a ride anywhere?"

Oh my god... now what do i say?! I couldn't think quickly enough, when I stammered out that I had missed my stop and that I guess I would just wait for the next southbound train to get back, she offered me a ride, "don't be silly," she said, "I can give you a ride back to your station."

Well, now I really didn't know what to say, how could I tell her my station was a good 30 minute drive south, how dopey could I be to miss my station by that much? My first instinct was to decline the ride, to save face and tell her I was fine, that I really wouldn't want to put her out. But something came over me and I told her the truth. I don't know what it was that drove me to say it. I couldn't believe that the words were coming out of my mouth, "Well, to be honest, I live in White Plains and I've spent the last 30 minutes riding the train trying to get up the nerve to ask you for a drink and dinner." I'd heard lines like this from guys before, but never thought I'd actually deliver it to another girl.

She broke into a big, adorable smile and laughed. "Well, hop in because I was hoping to ask you the same thing." I couldn't believe it, I was floating on air as I walked toward her car and opened the door to get in.

She smiled as I got in and said, "I'm Wendy." I replied that my name was Courtney and we drove out of the parking lot. I've never been so excited and terrified as I was at that moment. I was a mess. I could feel myself trembling. My hands were shaking. I thought to myself, what am I doing?

Wendy smiled at me and must have sensed my nervousness saying, "you poor thing, you really look like you could use a drink, I know the perfect place." She was so calm and self assured which only made her that much more attractive to me. And hardened my resolve to be cool.

I mustered a smile and laughed as much to disarm my own tension as anything else, "yes, you have no idea how nerve racking it is to ask a woman out."

She laughed, moved her hand from the stick shift to my thigh and with a gentle pat and rub of my thigh, assured me that she did.

Her hand returned to the stick as she drove fast through the narrow winding roads, as we chatted all the while helping to put me at ease and restore my confidence. It didn't take long before we pulled up to what appeared to be a dive bar. "Trust me," she said, "it's much better than it looks. Besides, I know the bartender."

We walked in to the bar, empty but for two older men at the end of the bar watching sports on the TV and the bartender, a model gorgeous girl with long black hair and blue eyes. The bartender lit up when we walked in and came out from behind the bar to give Wendy a big hug and kiss. Wendy introduced me, "this is Courtney, I picked her up on the train."

Her name was Tori and she was very thin but looked fabulous in her black t-shirt, blue jeans and cowboy boots. Wendy later told me, but some how I had immediately sensed it anyway, that Wendy and she had once been lovers. We took a seat at the bar and Wendy asked Tori for 2 cosmopolitans. I briefly considered objecting but quickly thought better as I really needed something a bit more potent than wine now anyway.

We sat facing each other on our bar stools, and I couldn't help but stare into Wendy's eyes, they were so deep and dark and captivating. She had taken off her long jacket before sitting down revealing a white blouse with French cuffs that was unbuttoned enough so when she leaned forward as she sat down it afforded me a clear view of her white lacey bra that appeared to be supporting very ample breasts.

Tori placed our drinks in front of us on the bar. We toasted Metro-North Railroad and sipped our cosmos. Tori stayed and chatted with us for a bit and then winked at Wendy as she said, "I'll let you two have some time alone." Tori left us to join the two older men at the end of the bar.

With Tori gone, Wendy began flirting relentlessly and I felt her foot run up my leg. Now this was a move I have used countless times with guys I have flirted with but suddenly a girl was doing it to me and I began to tremble with excitement. Trying my best not to let it show, I continued to sip from my drink as I rambled on about myself.

Soon, Wendy had moved very close to me, our legs virtually entwined together, she would touch my thigh, my hand, my shoulder as we spoke, I loved the attention but suddenly was completely unsure of how to react. I mean, I'm well practiced in the flirtatious advances of men, but this was so different than being with a guy. The rules must be different, I thought, how do I respond? At that moment, there was a pause in the conversation. We just stared into each others eyes for what seemed like minutes. I could feel the wide smile that seemed plastered on my face.

And then, Wendy moved her head from side to side to take a quick peek around the bar. Tori and the two older men were staring at the TV as the men provided commentary. Wendy turned back to me, shrugged her shoulders slightly, raised her eyebrows and smiled devilishly as she leaned in and kissed me. A soft heavenly kiss on my lips. As she pressed her lips against mine she parted her lips ever so slightly. My eyes reflexively closed and I instinctively parted my lips as well. Our tongues met. My heart raced. And time seemed to stand still for that moment.

Wendy broke the kiss and slowly leaned back in her seat with a wide toothy grin, she heaved a big sigh and giggled like a schoolgirl. I melted. Then I remembered where we were and looked around anxiously.

Again, Wendy must have sensed my anxiety and finally mentioned the unspoken, "this is the first time you've been on a date with another woman, isn't it?"

A date?! I hadn't considered that we were on a date, but clearly we were! I laughed nervously, "does it show?"

At that, Wendy took my hand and told me she was really attracted to me and really enjoyed my company but she didn't want me doing anything that made me uncomfortable. I began to object but she stopped me quickly and said, "you do know that I am a lesbian, don't you."

I gulped, of course I knew I was flirting with another woman and that she had effectively seduced me, but for some reason I never considered that she liked only women. This was a purely sexual flirtatious encounter, nothing more, nothing less, right? And then I was overcome by the realization that she might perhaps have more in mind than a chance encounter and I would not be prepared to deliver.

"Wendy, I find you extraordinarily attractive too," I began to explain. "You made my heart jump when I saw you on the train. You've made me tremble sitting here flirting, but I'm not a lesbian. I am just a girl that..."

She raised her hand and placed a finger over my lips to stop me and smiled. "Stop, I know you're not a lesbian. That's o.k."

"How did you know?" I asked, suddenly feeling almost hurt that I had been so obvious.

"I didn't," she said quickly, "at least not for sure, until I kissed you." I must have given her that puzzled kind of look with my head cocked that dogs give, because she bluntly added, "You kissed like a straight girl."

I was incredulous, "and just how does a straight girl kiss?"

She paused for a moment and tried to explain, "I don't know it's different. It's harder I guess. It's just something you feel."

Well, now I had been challenged and I never back down from a challenge so I bit my lower lip, batted my eyes and flirtatiously replied, "I bet I can do better if you try again."

She looked back at the three at the end of the bar and this time she took my hand, rose from her bar stool and led me to the back of the bar to the ladies room. Safely out of view, she lightly pushed me against the wall, placed her hand softly on the back of my neck and gently pulled my face to hers as our lips met for the second time. Pressing her body against mine now, we kissed deeply. Her hands explored my body. I instinctively wrapped my arms around her. I felt as though we were one and lost myself entirely in this incredible moment.

"Get a room," Tori's voice sang mockingly as she abruptly interrupted the moment.

Wendy laughed as she let go of me and replied, "caught." And immediately, my initial embarrassment vanished.

I began to laugh too as I looked at Wendy and suggested, "perhaps we should." Wendy agreed and after paying for our drinks, she took my hand and led me out of the bar to her car.

It had been a very long time since I felt so excited and happy just being with someone, as I did walking out of that bar with Wendy. We couldn't stop giggling as we jumped in her car. After starting the car Wendy leaned across to me and we locked lips in our third kiss. Again, I reflexively closed my eyes as our tongues met and my body tingled all over. Wendy, pulled away slowly, smiled and teasingly said, "getting better."

The competitive side of me couldn't help but answer, "you ain't seen nothing yet."

Honestly, I don't remember much else about the car ride to her place. We didn't talk much. We would just glance at each other and smile or giggle. I was in seventh heaven. She could have taken me anywhere and it wouldn't have mattered as long as we were together. The anticipation of being alone with Wendy was running through me like an electric charge, I could barely sit still. Finally, we pulled into the driveway of a small house and Wendy announced, "home sweet home."

We practically ran to the door and Wendy fumbled with the key for a moment before opening the door and ushering me in. We entered directly into a small but very cute living room and I could see the dining room through French doors to the left of the living room and on the right were stairs. I didn't have time to notice much else because Wendy took my hand and led me up those stairs to her bedroom. I did notice another bedroom that was clearly lived in and asked if she had a roommate.

"uh huh, I live with my sister, but she's a nurse and works nights," she answered reassuringly as if to anticipate my next concern of possibly being interrupted.

Her bedroom was small. There was room for a dresser, dressing table with a mirror and chair and a queen size bed that Wendy led me to. We stood at the foot of the bed as Wendy took me in her arms and we kissed deeply, for much longer than we had before. Wendy's hands wandered. I felt a hand on my breast softly massaging it while the other found its way to my ass at first gently grabbing it, then reaching down to the hem of my skirt and hiking it up my thighs. Wendy began kissing my neck and I leaned my head back inviting her heavenly kisses that now trailed down my neck to my chest and my exposed cleavage as her fingers expertly unbuttoned my blouse. Pushing my blouse of my shoulders it fell to the floor. Her kisses trailed to my shoulder and down my arm before she stepped away for a moment.

Wendy looked at me with a smile as she wiggled out of her pants, sliding them over her hips and down her firm thighs, stepping out of them. Standing up in just her panties and blouse now she had such firm, toned legs. She guided me to sit on the bed as she straddled my lap and we kissed again. She held my face in her hands as she kissed me and slowly rocked her pelvis back and forth, pressing her crotch against mine. I was ablaze with passion and my panties were drenched. She reached her arms behind me now and unhooked my bra freeing my breasts as she tossed it to the floor. She cupped each breast in her hands and leaned forward to place soft kisses on my nipples before wrapping her arms around me again. Continuing her pelvic thrusts Wendy held me tightly, her large, soft breasts, pressing against mine through the thin material of her blouse and bra as I held on tightly to her.

Her embrace was bliss. I've never felt so content and secure in another's arms before. I was hers completely now. As she guided me onto my back, now straddling my stomach she slowly unbuttoned her blouse and threw it to the floor before reaching her arms behind her to unhook her bra and toss it to the floor as well. As her large round breasts bounced free from the constraint of her bra I was struck by just how large they were for such a petite girl. And even more struck by how beautiful they were. I had never looked at another woman's breast quite like this before. With such longing and desire. I reached my hands up and took them into my hands and gently massaged them.

Wendy arched her back slightly and sighed as my hands explored her breasts. Reaching behind her, Wendy began some exploring of her own as I felt her hand run down my stomach to my panties. She ran her hand over my mound rubbing it through my panties before eventually pushing my panties aside. Her finger lightly parted my lips and found my clit which she ever so gently began to tease with her finger. Her touch was like nothing I had felt there before and my body soared with delight.

Wendy climbed off me now and positioned herself between my legs. Hiking my skirt up all the way to my waist, she rolled my panties down my legs and began kissing my toes. Running her tongue along the arch of my bare foot then taking my toes in her mouth and sucking. I felt her hands run up my calves to my thighs as she gently kissed and licked her way up my legs. Finally reaching my crotch. Oh my god, I was not prepared for this as she nuzzled her face into my now soaking wet pussy, running her tongue around, parting my lips with the tip of her tongue, teasing my clit. I lost track of all that she was doing down there as I threw my head back in ecstasy. I'd never felt anything like it before. I ran my fingers through her auburn hair, pressing her face tightly against my pussy as I writhed and moaned uncontrollably. And with that I came in a rush that sent my entire body to heights of ecstasy I had never experienced before.

As I lay exhausted, yet exhilarated on my back, Wendy climbed up next to me and asked with an evil grin, "did you like that?"

I could barely speak I was breathing so heavily, "oh my god, yes," I blurted out.

"Good," she said with that same evil grin, "because now its my turn."

With that she straddled my chest and moved herself up to position her pussy above my face. I really wasn't sure what to do, but Wendy gave me no time to worry about it as she lowered herself onto my face. I took in her sweet aroma as she lowered herself on me, pressing herself against my face, so soft and wet and warm. I had little choice but to get right to work exploring her pussy with my tongue doing my best to try to do all the things I know I like so well.

From the sound and depth of her moans, I figured I must be doing o.k. I grabbed Wendy's ass with both hands as she rode my face. Her juices covered my face and ran down my cheeks. Then I felt her lean across the bed as I continued. She reached into her nightstand and came back with vibrator. She turned herself around putting us into a 69 position and as I continued to lick and suck on her pussy, she began to tease my clit with the vibrator. Oh my god, she was going to make me cum a second time, I thought, before I can get her to cum just once. As if sensing my anxiety again, Wendy instructed me to use my fingers too. So I began to slowly slide my finger into her, slipping it easily in and out. Wendy moaned and said, "that's it baby, now more."