My First Experience With a Woman

Up to this point I had never been with a woman and never really even seriously considered it, granted Clive had mentioned it a couple of times on and off when he was feeling particularly horny , probably more as a fantasy for him than for me.


My sexual experiences were pretty varied and full to date and I was very satisfied with where I was and who I was doing it with, that was until I met Tiffany. I genuinely had never thought I would be attracted to a woman but Tiffany was absolutely gorgeous and exuded sexual energy.

We met at a club and I was mesmerized the minute she walked in. From her fiery, red hair, porcelain skin, pouty lips, and voluptuous hourglass figure. She turned every head as she walked across the patio in her tight cut-off denim shorts and black tank top. I was at a complete loss for words when she approached me and introduced herself as she poured a drink.

I felt very self-conscious of my figure in comparison to hers, as we made small talk, I am five foot five tall and my breasts are at best a B/C cup, but I did try to keep in reasonable shape have pretty good legs and had a fairly tight body.

To my surprise and delight Tiffany and I hit it off immediately, We had a great deal in common from our love of sport and musical interests. We became good friends and started hanging out almost every week over the next six months or so. I soon learned that Tiffany was very sexually adventurous and went into great detail telling me about her exploits with both men and women. She was a strong character and a self proclaimed nympho and totally unashamed, which impressed me.

I have to admit that her stories often left me very turned on and if Clive wasn’t available I would find myself laying in bed at night rubbing my clit as I imagined Tiffany having sex with the partners she had described to me, imagining Tiffany laying on her back with her long smooth legs in the air as a muscular hunk drove his big hard cock into her. I imagined her moaning and crying out with pleasure as a cute girl licked her pussy and fingered her to orgasm. I imagined her doing pretty much everything as I played with my wet Pussy , but I never actually imagined myself with Tiffany. Until one day everything changed.

Clive was away working again for a couple of days so Tiff and I had spent the afternoon in the park sunning ourselves and watching some guys playing volleyball before making our way to one of the local bars. The drinks were going down well that night and before I knew it I was quite drunk and definitely in no condition to drive home. Tiff suggested that we share an Uber back to her place have a couple more drinks and then I could crash there since it was closer, it seemed like a great idea to me.

We arrived at her one bedroom flat and we both stumbled inside laughing and giggling like a couple of schoolgirls going over the days events. Tiffany had barely shut the door behind us before pulling me against her in a crushing embrace and pressed her full lips against mine. Then almost as quickly as she had kissed me she pulled away and looked me straight in the eyes.

“Lynda, I want you so bad right now,” she whispered as she ran her hand up under my dress and caressed my thigh.

“But...but I’ve never been with a woman,” I managed to stammer as her touch was raising goosebumps on my flesh.

She kissed me again softly her tounge darting between my lips.

“Shhh, it’s ok I’ll show you.”

To be honest that was all the encouragement I needed. I was a little drunk and more than a little horny as Clive had been away for three days now and Tiff was a stunning woman so I pressed my lips hard against her’s, responding in a deep kiss. My hands began to explore her body, I reached round her hips and squeezed her firm round ass cheeks as my tongue continued to explore the inside of her mouth, as I ran my hands across her ass cheeks again Tiff let out a soft moan of pleasure . She pulled away from me and pressed me against the wall lightly kissing down my neck, I felt goosebumps appearing on my skin as her hands lifted the hem of my dress and pulled it up over my head leaving me just in my bra and panties.Then as she continued to kiss her way down my neck and across my chest I felt her fingers begin to rub my pussy through the thin fabric of my underwear, I whimpered with pleasure as her touch sent little electric shocks through my entire body. Her touch was so much lighter than I had experienced before with guys and she knew exactly where to touch me and what pressure to apply, my knees buckled slightly and I let out another soft moan of pleasure.

“Oh, Tiff I’ve wanted you for so long,” I have fantasied about this and you for months now babe. I arched my back a little as I felt Tiff reach behind me and un fasten my bra , my boobs fell free as she removed it fully before cupping my left breast and taking my nipple into her mouth, drawing it between her lips and making it almost instantly rock hard with pleasure.

“Good, I have so much to show you Lynda,” she said with a grin as she took my hand and pulled me into her bedroom.

Before I knew it Tiff was gently but firmly pushing me across the room to the bed until I was sat on the edge facing her, again she licked, nibbled and kissed her way down my neck to my breasts, this time she licked and sucked on both of my nipples in turn until I was flushed red with excitement and panting with need. I reached forwards and in buttoned her shirt and pulled it open and down off her shoulders , then it was time for me to reach forwards and unfasten her bra behind her back and release her large breasts from their confines , as I did so they bounced free and I took a moment to simply admire them, they were much larger than mine but still very perky with huge dark nipples , I put one hand under her right breast and lifted it up with my thumb brushing against her nipple, Jesus it was so heavy and so soft and smooth. Tiff stood up and sat on the edge of the bed next to me taking my lead from her I rolled her over to her back so I could further explore her body.

Tiffany certainly had the most beautiful breasts I had ever seen, While they were undoubtedly large, the largest that I had ever seen and even laying on her back they were still perky and firm. They were adorned with big rosy, pink nipples that were standing erect and begging for my attention. I kissed her as I caressed her breasts, enjoying the feeling of their weight in my hands, I moved my fingers to her nipples and teased and lightly pulled on them eliciting a low moan from her. I lowered by head to her chest and traced one of her nipples with my tongue before gently sucking it into my mouth. My hands continued their exploration down her body, over her taut stomach, down her thighs and back up to stroke across her cotton clad pussy. The entire time I took turns licking and sucking on her nipples till she was moaning and wiggling from my attentions.

“Oh for someone who has never been with a woman you are doing amazing,” Tiffany whispered in a low husky voice as she rolled out from under me and swiftly pinned me to the bed on my back, “but let me start and show you what it’s all about Lynda.”

I was more than happy to totally give in to her , I was breathless and my heart pounding with anticipation as she kissed her way down my chest and over my stomach as her hands slid my panties down my hips and off over my feet. I could feel the wetness between my folds increasing and I was getting desperate to feel her touch down there. She raised up and pulled my face to hers and kissed me hard on the mouth, her tongue pushing between my lips, exploring and teasing. Her other hand snaked down my body and I gasped when her fingers slid between my slick folds and up to my clit. Responding I kissed her, moaning into her mouth as she strummed her thumb over it in rhythmic circles and worked her finger in and out of my Pussys hot wet folds. Before long I was moving my hips gently and grinding against her hand and when she brought her mouth back to my breasts I was at the precipice of an orgasm. Tiff could sense my building passion and abruptly stopped and pulled her hand away from my now drenched pussy. She smiled a devilish grin looking me in the eyes as she licked her glistening fingers.

“You taste absolutely delicious,” she cooed as she moved down the bed and kneeled between my trembling thighs. She placed her left hand on top of my pubic mound and used her other to gently spread my now slick folds. She began to lay long, slow deliberate licks from the bottom of my lips up to my clit where she would pause for a moment as she flicked her tongue around the sensitive nub. After only a few minutes of this slow teasing I was begging for more.

“Oh, Tiff, so good.”, I stammered as I reflexively thrust my hips towards her mouth. She smiled up at me and worked first one then two fingers into my wet Pussy, I moaned loudly as she curved them upwards and stroked the sensitive mound of flesh along the front wall of my vagina. She continued with her oral assault, now paying more attention to my throbbing clit. My brain was reeling and I was panting as she continued working her fingers in and out. I was climbing the precipice of orgasm again and I wasn’t going to let her stop this time. I grabbed the back of her head and ground my pussy into her face. She then sucked my clit into her mouth and flicked her tongue over it repeatedly and she thrust her fingers into me faster.

“Oh fuck yes, don’t stop!” I moaned and thrust my hips towards her face.

This time she didn’t stop but continued her efforts until I was writhing with pleasure underneath her, I felt my orgasm coming, but also an intense pressure in my nether regions and the urge to urinate. My thighs were trembling around her head and I gripped the bedsheets as I panted and moaned in pleasure.

“Oh shit!” I screamed as my orgasm exploded and I felt warm, liquid gush out of me.

Laying there still moaning and completely wrung out as Tiff cooed her approval and continued to lap at my sensitive pussy. Finally I couldn’t take anymore and pushed her head away and clamped my thighs shut. She crawled up my body smiling and sensuously licking her lips.

“Lynda, you never told me you were a squirter!”

“I didn’t know I was! Is that what that was, I thought I had peed. Fuck that was amazing!”

“Most women can if things are just right,” Tiffany replied as she rolled over and laid down next to me with a glint in her eye.

I took this an an invitation to repay the favor and I didn’t need another, Tiffany looked absolutely stunning stretched out on the bed, Her red hair was flowing around her, and her full, perky breasts adorned with rosy nipples. I was trembling with desire when I knelt between her legs and as she had done eased her panties off her hips and down her legs, it was then that I caught my first glimpse of her beautiful pussy. She kept her auburn hair trimmed into a small strip and she had a large clit adorning her pronounced pink inner lips. I ran my index finger from her clit down between her lips causing her to moan softly.

“Mmm, go on babe. Don’t be shy,” she said with a grin.

I lowered my face towards her inner thigh and kissed the soft smooth white flesh between her legs, Tiff parted her legs a little more and as she did I saw her Pussy lips part and glisten with her building pleasure. I changed my position slightly and I began to lick up and down her moist slit. Her taste was something entirely unique, sweet with a musky hint of tang to excite my tastebuds. I delved deeper, spreading her lips and flicking my tongue across her engorged clit until she was moaning and running her fingers through my hair. I sucked on her clit and her lips as she began to moan and wiggle her hips under me. I took this as my cue to increase my efforts so I slid two fingers into her warm, wet channel and began to pump then in and out as I lapped up her creamy juices.

“Oh god that’s it!” Tiffany exclaimed as she arched her back and pinched her nipples.

I murmured my appreciation into her pussy as I stroked the tip of my fingers along the upper wall of her now soaking hole. I sucked her large clit into my mouth and licked my tongue across it until I felt her legs begin to tremble.

“Fuck!” She screamed as I was rewarded with her juices squirting into my mouth and down my chin.

Tiffany’s body relaxed and she lay there panting as I finished lapping up her creamy juices.

“Oh my God, this is amazing! I can’t believe I’ve been missing this all these years,” I said is I crawled up next to her in bed and kissed her full lips.

“Oh babe we are just getting started, that is nothing,” Tiffany giggled, as she hopped off the bed and skipped out of the bedroom. I had just caught my breath when she returned a few moments later with two glasses of ice water. She offered me one and I took it and gulped half of it down.

Tiffany set he glass on the bedside table and walked to the closet. I watched entranced my the seductive sway of her full hips. She pulled down a basket from the top shelf and set it on the bench at the foot of the bed giving me a mischievous grin.

“What’s in there?” I asked as I set my water glass down and crawled down to the foot of the bed.

“Oh, just about any kind of toy a girl could ever want,” she replied and held up a hot pink double ended dildo.

My curiosity was piqued and I began to rummage through the basket. There was certainly quite a variety. There was a plethora of dildos in a variety of colors, shapes and sizes (some that seemed too large to even use), vibrators, wands, anal plugs, beads, and several different harnesses.

“Wow, do you use all of these?”, I asked holding up a very large black dildo.

“Oh yes, sometimes it just feels so good to be really stuffed,” she purred in reply.

I looked at the enormous dildo in wonder. I couldn’t imagine it fitting anywhere in my body nor less feeling pleasurable. Tiffany must have saw the concern etched across my face.

“Don’t worry we will start with something smaller. Now lay back and relax, because I’m going to make you feel so good,” she said with a grin and wiggled the pink jelly dildo. I had never used anything but my fingers and a Rabbit to masturbate with and was a bit nervous but I did as asked and I reclined on the bed and spread my legs for her. She dipped her head down and gave my pussy several long, slow licks again before spreading my puffy outer lips and probing my hole with her tongue.

“You have the cutest little, pink hole, Lynda Perfect and tiny just like the rest of you,” she purred as she started to run the head of the dildo over my pussy.

She continued to tease my pussy, just barely pressing the head against my hole as she licked and sucked on my clit until I whimpering and grinding against her.

“Mmm, you want me to fuck you baby,” Tiffany cooed as I nodded my head enthusiastically.

“Oh yes, please stick it in,” I begged.

My hole was well lubricated and she met little resistance as she sunk the first several inches inside me. She continued to lick and suck my pussy as she slowly worked the dildo in and out of me. She continued this for several minutes gradual thrusting faster and harder till I was taking over half of the toy in my Pussy . I was climbing the precipice to another orgasm when she stopped.

“Mmm, I think I need some cock too.”

Leaving the plastic cock inside me she flipped around and entwined her legs around my body before sinking the other end of the dildo in her own pussy. She scooted forward till our slick pussies were touching and began to thrust and grind against me. I quickly picked up the rhythm and moved with her. The feeling of our pussies sliding against each other and being full of cock was the most erotic sensation. We moaned, gyrated and grinded our way to orgasmic bliss until we were both exhausted and panting.

I slept contentedly that night in Tiffany’s bed with her legs wrapped around me. I awoke in the morning feeling slightly ashamed of our drunken tryst. I slipped on my clothes and snuck out of her flat leaving her sleeping peacefully, with her beautiful auburn hair spread out around her.

As I walked home in the early light of morning and tried to sort through my jumbled thoughts. I chalked it all up to a drunken experience and tried to bury the feelings and excitement that Tiffany awoke inside of me. I assumed that this would likely be a one time fling, but I could not have been more wrong about what was to come.