My Affair with Wendy

My relationship with Wendy had started innocently enough. I had broken up with my husband and was finally beginning to circulate again. This had led me to be at one of my co-workers favorite watering holes, a trendy, upbeat thirtyish bar one night after work. Somewhere between drinks and shop talk I found myself on the dance floor and when I looked up, she was there, dancing with me. Early thirties, brown hair, brown eyes, light skinned with a honey colored tan, Wendy was eye candy. About 5’8” her body was long and slender with a hint of masculinity. Her breasts were small but well formed, likely a B cup, and beautifully proportioned with the rest of her body.

We didn’t talk, in fact, she did not acknowledge I was there. Nevertheless we moved to the music…together. By the end of the song there was no doubt we were with each other. She took my hand and led me back to the bar.

“Tara, isn’t it?” she inquired.

“Why yes…but how…”

“I’m an attorney, I specialize in litigation. Hardly makes me shy about asking who you were. I’m Wendy and I had to meet you, it’s not every day a beautiful woman joins our little group here.” Her voice exuded confidence, assertiveness with a hint of playfulness.

The remark ‘beautiful woman’ felt good, I was mildly embarrassed. But it was soothing, my ex-husband hardly ever expressed his feelings and if he had it was usually critical. In fact it had been a long time since I thought of myself as a beautiful woman, call it ‘self unawareness’, I was oblivious to how my appearance was viewed by others. I remember a friend once remarking to me. “You have no idea how people look at you when you enter a room…do you?” He went on about how both men and women were easily distracted by my presence…then proceeded to make a very discrete pass, which I had left unacknowledged.

In my mid-thirties I had taken good care of myself. Medium height and build I had black hair and dark brown eyes blended nicely with a creamy white complexion. My breasts were large and full with dark silver dollar sized nipples. Only slightly heavier than I wanted to be through the middle, my legs and butt were well toned thanks to my exercise regimen. I suppose I did look ‘hot’.

“Thank you, Wendy, I appreciate the flattery,” I answered politely.

“Yes…but where will it get me?” She grinned then laughed as she said it.

As it turned out, it had gotten her everywhere. Wendy was a fascinating woman and in a very forward yet charming way had seduced me that night. I found myself going home with her. Her condo was fabulous, well decorated, finely furnished, and a master bedroom complete with floor to ceiling mirrors. Wendy was smart, aggressive, she knew what she wanted and once she sensed my acquiescence she moved in for the conquest. Perhaps she even knew that I had not had sex in a while or even that it was one of those times when I was particularly aroused. She had brushed against me repeatedly while at the bar and had run her hand down my back and lightly squeezed my ass. I’m sure I squirmed as she did it and the sly grin on her face told me she had noticed.

Once at her condo I had followed her into the kitchen where she was to pour us each a glass of wine. We never got to the wine. Instead she kissed me passionately and then forced me up on the center island counter. Her hands folded my skirt up underneath my butt revealing my pale blue panties, a dark stain in my crotch confirming my readiness. She swiftly laved her way up my smooth inner thighs then kissed her way up the outside of my soaked panties. Her teeth clamped on the delicate fabric, she slowly and sensuously pulled them down and completely off.

“Mmmmm…I love the smell of your pussy Tara,” she said as she held the panties to her face. “Let me guess…haven’t been fucked in a while have you? Just not the same having to pleasure yourself all the time is it?” She taunted teasingly.

I moved to sit up on the counter and almost slid off, my wetness making the smooth top slick and wet. Wendy locked her arms around my hips and then used her hands to spread my neatly trimmed pussy wide open. She paused for a second, almost as if admiring the view, then rocked me back gently to force my pussy up toward her. I felt her spit into my core and let out a short moan as her tongue probed deep into my recesses. One of her hands strayed up to my breast, grasping it, then squeezing and twisting my taut nipple through the light material of my bra until I felt a stinging stab of pain. She released quickly and I felt a sensational rush to both my pussy and my nipple as the pain subsided.

Wendy’s tongue, she had the largest and longest I had ever seen, worked quickly and expertly up and down my hot slit, rimming my asshole, and then flicking and teasing my engorged clit coaxing it from its sheath. I was completely helpless. Wave upon wave of passion washed over me as she worked on me relentlessly. My whole body shuddered as the first orgasm took hold followed up by countless aftershocks. I screamed and clawed at her back as she sucked my engorged clit drawing it between her teeth then lightly nipping at the base.

“Please Wendy…no more.” I finally gasped, breathing heavily and totally exhausted from her efforts.

She paused and her eyes met mine, a deep, penetrating look as if peering into my mind trying to read my innermost thoughts.

“Are you telling me you didn’t like that?” She questioned.

“No…no not at all…it was just…just so intense.” I was still breathless.

“Good, then you’ll be back for more,” she smiled as she helped me sit up then embraced and kissed me deeply.

It was the beginning of an incredible sexual experience. Wendy was a high energy, insatiable dominant. “Most men have little or no imagination when it comes to sex. I can please you in ways you never thought of, when you are with me always be ready.” She had instructed. I learned to expect the unexpected.

One night just before a dinner date Wendy had been unusually attentive. She insisted on us taking a limousine to the restaurant. As we relaxed with a glass of champagne, enjoying the ride, she had slid her hand underneath my light summer dress. Her fingers traced along my mound then lingered by my clit, slowly rubbing and massaging it through my silk panties. She kissed me and pressed her body against mine, I could feel my nipples hardening as she carefully caressed my breasts. By the time we arrived at the restaurant, one of the finest in the city, she had me very wet and very hot.

“Why Tara you look a little flushed,” she teased as we were seated. Wendy had insisted on a secluded corner of the restaurant and, other than an older couple sitting at a nearby table, no one could see us.

“Only you would do this to me…fine restaurant, great food, and I feel like I’m in heat.”

“I think you are baby…in heat for me,” Wendy looked at me seductively. “You could relieve yourself right here, right now.”

“Sure and they’ll throw us out,” I said with a note of disgust.

“Not necessarily, not if you are quiet and discrete. I would find it incredibly erotic if you could masturbate for me…right here, in fact, all through dinner.” She was serious.

“But…how?”

“Take off one of your shoes.” She commanded. It was a warm summer night and I was wearing light sandals, I unhooked the strap and the shoe slid off. As Wendy and I talked I noticed the older man at the nearby table, his wife’s back was to us, watching us as nonchalantly as he could without drawing either her or our attention. “Now bring your leg up underneath you and sit on it.”

I tucked my leg underneath me positioning my heel strategically under my pussy. I felt the pressure as I settled onto it. In my heightened state of arousal even this slight movement had me squirming with anticipation. “Rock backward and forward over your heel…not so fast…slowly.” Wendy instructed. I felt a gush of wetness as I slowly moved my pussy over my heel.

Wendy stared at me approvingly, smiling broadly, as she watched me build to orgasm. Our waiter seemed to intuitively know what was happening. I could barely control myself by the time he came to serve our bottle of Pinot Noir. Wendy seemed amused as the waiter most deliberately took his time uncorking the bottle and then decanting the wine. I was ready to explode by the time he left. “Let it go baby.” I heard Wendy say, her voice barely above a whisper.

I muffled a deep moan and closed my eyes as the first orgasm took hold. As the initial wave passed I opened my eyes immediately catching the glance of the older man nearby. He smiled, knowing exactly what he was seeing, and enjoying every minute. “Is our curious neighbor enjoying the show?” Wendy had asked. I nodded and continued grinding my heel into my pussy.

By the time we left the restaurant my panties were soaked in my juices, my pussy was hot, swollen, and ready to be fucked. Wendy teased me on the way back to the condo. She slid her hand inside the wet crotch of my panties, and traced her fingers around my slick slit. We kissed deeply, passionately, and she caressed my breasts.

We seductively stripped each other in the doorway of the condo, our bodies silhouetted in the moonlight. Wendy led the way to the bedroom pausing only to smell my wet panties. “Hands and knees, on the bed,” she commanded. “Tonight I’m going to make you ‘squirt’.” Wendy then casually inserted two fingers into my pussy, sliding them in gently she immediately searched for my G spot. My gasp betrayed its location. Her thumb slipped up to my engorged clit lazily rubbing around it carefully avoiding direct contact.

Wendy worked slowly, deliberately, building rhythm and intensity over what seemed like an eternity. I was helpless, she had me completely in her control. I felt a sensation building inside me, similar to an orgasm yet different. Wendy continued to work her magic, kissing and caressing the back of my neck, gently cupping my breasts and lightly pulling my taut nipples. I was in heaven.

“You will come to a point where you think you are going to urinate, but you won’t, you can’t. Don’t tense, just relax baby. You’re in for the experience of your life.” Wendy instructed.

The sensation continued to build and soon her prediction came true, I felt an urge within me and was about to stop when Wendy’s hand gently rubbed over my urethra providing temporary relief. “Go with it,” she encouraged. As I did I felt an incredible surge from within me and felt my body release streams of hot liquid. The feeling was intense and satisfying as my body twitched involuntarily. Wendy kept going rubbing gently but more quickly on my G spot. The feeling of urgency returned, but I relaxed and was rewarded with another spurt of hot liquid. “Oh yeah, that’s my girl,” Wendy smiled.

I had always thought female ejaculation was a myth, now was living proof that it was real. Wendy and I spent much time exploring our bodies, inducing each other to ‘squirt’, and now could do so very easily.

Bringing Wendy to orgasm during our lovemaking was always a challenge. She would never completely let go, preferring to concentrate on bringing me with her or at least setting me up for an orgasm shortly after she came. Usually we ended up in a sixty-nine position with me on top. I would tongue her clit while pumping her tight pussy with my fingers. As I would increase tempo on her she would counter on me. Most often I would become completely distracted, panting for breath, unable to continue on her.

“Ah, that’s my sweet slut…come for me,” she would encourage. Wendy would then increase the intensity of her assault, kissing, licking, sucking, and lightly biting my clit. My screams spurred her on as she drove me over the edge of an intense orgasm. I would collapse onto her, body twitching, as she would drink the juices from my wet pussy.

But I did have my way with her. Wendy and I often worked out together. She enjoyed intense high impact aerobic sessions where she would work herself into a full sweat. I was encouraged to join in although I limited my participation, I simply did not have her physical ability. One day, when it was particularly quiet in the gym, I disappeared to the locker area after we had finished our workout. Wendy was recovering on one of the benches.

I quietly returned and sat down behind her, massaging her neck and shoulders, kissing her lightly on the cheek and nibbling at her ear lobes. Wendy was still hot and sweating profusely as I slipped her perfect small breasts out from under her sports bra. Her tiny red nipples become hard and erect as I flicked and rolled them between my thumb and forefinger. Wendy glanced behind me and smiled, as she noticed a leather strap-on cinched around my waist.

“Time for a shower, come with me.” I commanded, and led the way.

Wendy moaned as I bent her over in the shower in front of me. I could see the water dancing off her back and running down her beautiful breasts as they hung down beneath her. Dropping my hand between Wendy’s legs and along the smoothness of her shaven pussy I felt for the wetness of her core. She was definitely ready. I slowly positioned the tip of the huge phallus between her swollen labia and worked it up and down her slit. Wendy’s moans grew louder as I slowly penetrated her.

“You like my big cock don’t you?” I asked forcefully. “You want me to fuck you with it?”

“Oh sh-shit, I love your big cock,” she gasped.

“And you want me to fuck you with it, don’t you? Tell me you want me to fuck you with it.” I demanded.

“Y-Yes. Please fuck me, fuck me hard,” she pleaded.

With a heavy thrust I buried all eight inches of the dildo in her pussy then began rhythmically pumping her. Her legs parted further as she balanced and I could feel her moving back onto the dildo as I thrust forward causing a distinct smacking sound as small fountains of water were driven up over her back from the force of the action. Her moans became louder and I could hear her breath grow shorter. Sensing she was close to orgasm I reached around and fingered her swollen clit as I drove my fake cock deep inside her. Her reaction was instantaneous.

Wendy’s screams could be heard above the shower as she came. Her body bucking forward I held on to her thighs tightly and kept on pumping furiously. Wendy’s body shuddered and her screams turned to sobs. She was totally consumed as multiple orgasms coursed through her. Her knees buckled slightly but held up.

“Oh Tara, don’t stop, fuck me…fuck me harder!” She cried. I reached for her hair and taking a handful, gently but forcefully pulled her head back drawing her body up toward me. Her perfect breasts swung seductively as shock waves of my thrusts coursed through them. I let go of Wendy’s hair and reached around cupping both breasts as I made one final mighty thrust driving her to her toes and then holding her there, as if mounted on my phallus, for what seemed to be forever.

Wendy finally collapsed into my arms and I kissed her and caressed her lovingly. She returned the kiss and held it long and deep. “God I love it when you fuck me like that,” she whispered.

“Not so bad being the submissive for a change.” I smiled as I stroked her forehead.

Predictably Wendy had had other women before we had met. Cassie had long been a friend of Wendy’s. They had graduated from the same college, both obtaining degrees, Cassie’s in Kinesiology, Wendy’s in Law. Cassie had gone on as a fitness instructor, personal trainer, and taught physical education at a local high school. Wendy confided to me that Cassie had been her first lesbian experience. She had taken an inexperienced Wendy and shown her the way of Sapphic pleasure.

Cassie was easily 6’ tall, strawberry blonde, with large tits and a very muscular build for a woman. Wendy recalled a time, during their lovemaking, when Cassie had lifted and turned her upside down, wrapped her powerful arms around her hips and lower back, then furiously licked her clit and pussy. Cassie had brought Wendy to orgasm while hanging upside down and she had nearly passed out from the experience. Wendy claimed she had never been fucked as long and as hard as when Cassie used a strap on. And on occasion Cassie would use a double dildo penetrating her ass and pussy at the same time.

Apparently Cassie’s toy collection was extensive and she was expert with their use having introduced Wendy to many exotic accessories that exhausted more than a few batteries. There was no doubt that Cassie had been a sexual mentor to Wendy and although their relationship had not lasted, they had stayed in contact with one another. Wendy had told Cassie about me and predictably, she had to check out the new talent.

Cassie was a little bit older than I had imagined, probably early forties, but she looked terrific. She had a wonderful sense of humor and teased Wendy unmercifully as they talked about their college days. Cassie had been married quite young and worked to put her husband through college. After graduating he abruptly left her but, she had gotten enough money in their settlement to fund her own education.

We enjoyed a number of glasses of Chardonnay. As I enjoyed the conversation I could see the furtive glances between Cassie and Wendy, they were up to something. Wendy made the first move. Slowly rising she casually walked around behind the sofa where I was sitting. Cassie watched her intently as she stopped behind me and lightly placed both hands on my shoulders and began massaging them.

“Ah, that feels good.” I shrugged and moved forward slightly. Wendy gently forced me back against the sofa and slid one hand down the front of the low cut neck of my jersey. She then slowly massaged the top of my breast. I leaned my head back and Wendy met my lips, we kissed deeply, eagerly chasing each other’s tongue deep into our throats. I felt wetness between my thighs.

Cassie moved as we began to kiss. I had on a pair a light summer shorts over white cotton panties. Cassie moved between my legs and began to kiss and caress the inside of my thighs. Wendy aggressively kissed and sucked my tongue into her mouth. Her hand expertly released my bra and she soon pulled it from under my jersey. I felt the coolness of the air conditioning on my tits as they swung free and the light abrasion of the material on my dark brown nipples.

Cassie released the front of my shorts and seductively removed them to my knees. One hand rubbed my pussy through the cotton panties, the other ran under my jersey to my breasts. Cassie pinched and rolled my nipples in her fingers making them harden, she then pulled and stretched them until they protruded a full inch in length. I moaned when Wendy finally released me from her kiss and deftly removed my jersey. Cassie nodded toward Wendy and then moved up to suck on one of my swollen nipples. Her hand dropped down the front of my cotton panties and found the way into my hot, wet pussy. Cassie moved her fingers expertly and soon had me writhing on the sofa ready to orgasm.

“Get off the couch Tara.” Wendy commanded.

As I rose Cassie quickly slid off both my shorts and panties. Wendy moved in behind me, kissed and caressed my neck, back, and face. Her hands moved to my breasts cupping and fondling them, flicking her finger at my nipples keeping them hard and taut.

Cassie buried her face in my hot, swollen pussy. She laved around the entrance then spit into my core. Her tongue stabbed into my hole driving deep inside me. I felt my juices flowing as I contracted to meet her advances. Suddenly Cassie stopped, moving up to concentrate on my clit. Using her tongue expertly she coaxed it out of its sheath and proceeded to flick it unmercifully. I quivered as Cassie’s tongue lashed my clit. She then brought her hand up to my pussy penetrating with two, three, then four fingers. I was close to the edge. I moved with Cassie’s finger and tongue as they rhythmically pumped me. Finally I screamed as I came, no longer able to hold back. My body convulsed, my knees buckled, and as Wendy guided me, collapsed back on the sofa.