Play Date at Connie's

Karen and I should have gotten married. The great sex should have shown us how compatible we were. But we were young and stupid, both lousy at understanding our feelings, and worse at expressing them ... so we never thought of marriage and eventually we split.

A few years later we were both married to other people, both with 3-year-old boys, and she was living on the other side of the country. We emailed a few times a year, but that was all. So I was surprised one day when Karen called.

"Hiya Brent. Guess who?"

"No guessing, sweetie. If ever I don't recognize your voice ... somebody should check my pulse."

We spent a few minutes catching up, then she told me why she called.

"I'm going to be in your lovely city next weekend and I think we should get together."

I had never met her husband and didn't really want to. But I thought I should offer to entertain.

"We could have you and Rob over to the house for a cookout Saturday," I offered.

"Rob's not coming," she said. "It's just me and Teddy."

"Okay, I'd love to meet your boy and we could still have that cookout."

She hesitated.

"Does Ginny still work weekends?"

"Yeah, her hobby has turned into a business so she's working 12-hour days on weekends. Brian and I run errands and go to the playground."

"So maybe you and Brian could break free and come over to Connie's for the day?"

I was a little surprised at the mention of Connie. Karen and Connie had been best friends through college, and roommates for several years. But Connie had not approved of me when I was dating Karen. She thought I wasn't good enough for her roomie. In those days she enjoyed teasing me about my often-interrupted college studies and my bartending jobs. Connie and I never actually fought, but our relationship was far from close.

Connie graduated at the top of her class and was a law professor. She was also married to a lawyer and had a 4-year-old girl.

"So ... you're staying at Connie's?"

"Yeah, she's got a big house with a pool. Her husband will be at some seminar in Chicago, but she's offered to play hostess. And I'm desperate to meet your little boy. I can't wait to see you being a Daddy!"

So we arranged to meet at Connie's house at midday the following Saturday. But before she hung up, Karen said something that started me wondering.

"You won't tell Ginny about our date, will you?"

I admitted that I probably wouldn't tell my wife I'd be seeing an old girlfriend.

"Good. Then we'll see you Saturday."

"Hmm," I thought, hanging up.

It never occurred to me that Karen has sex in mind because a few years into her marriage she'd developed VVS, or Vulvar Vestibular Syndrome. It's a little-known condition that makes sex painful or impossible. Her emails over the years gave me a few details and I gathered that her sex life had come to an end. Even masturbating was usually too painful. It was hard to imagine someone like Karen doing without sex, but she hinted she was celibate.

While waiting for Saturday to roll around, I found myself recalling some of the more intimate details of my time with Karen ... including some that involved Connie, at least second-hand.

Karen and I tried a lot of things in bed, and one fun thing was sharing our fantasies. That's how I found out Karen lusted after Connie.

At first she would only tell me she had fantasies about making love to other women. For awhile I enjoyed asking her if she was attracted to various girls we knew, and I had great fantasies of her fucking them. I amused her by asking about a couple of girls in particular.

"Why would I be attracted to HER?" she said, after I asked about one girl.

"Well, I know you like athletic guys and SHE'S athletic."

"Hah, you have no idea!"

She was right. When Karen finally revealed that Connie turned her on I was surprised, but intrigued. They had always been close, but her sexual interest apparently started once when Connie noisily fucked a guy on their couch while Karen pretended to sleep in a nearby chair. Something awoke in Karen when she saw Connie's small tits bobbing and heard her gasp through an orgasm. Karen realized SHE wanted to be the one making Connie come! She waited until Connie and her partner left, then quickly masturbated to a powerful climax!

So I started fantasizing about Karen and Connie fucking ... and then I started telling Karen about my fantasies.

The first time, Karen was on top, riding my dick when I told her, bit by bit, about my fantasy featuring her and Connie. I told her I imagined the two of them kissing and undressing each other. I told her about my vision of them suckling each other's tits, and I told her in vivid detail about them in a 69, licking each other to orgasm.

At each stage of my lurid tale, Karen got more and more aroused, more and more wide-eyed, more and more breathlessly out-of-control. By the end she was fucking herself up and down on my dick like crazy while gripping me hard enough to leave bruises. Then she was overwhelmed by a sudden, powerful orgasm! Her typical orgasm was marked by long, full-throated groans, but THIS one triggered an ear-splitting scream of joyful completion!

After that I would occasionally throw gasoline on the fire of our lovemaking by describing my fantasies of her and Connie making love. That never failed to drive Karen into a state of lustful overdrive resulting in a powerful climax for her and a sore dick for me.0

I once asked Karen why she never tried to live out her fantasies with Connie. As much as she loved the idea of sex with Connie, she wasn't sure how her best friend would react. Karen was afraid of losing Connie's friendship.

Saturday came, Ginny left at the crack of dawn and I puttered through the morning before dressing Brian and heading for Connie's. She lives in a seriously upscale neighborhood with huge houses surrounded by trees and tall privacy fences. Connie's house was one of the nicest, with six bedrooms, a huge kitchen designed for entertaining and a beautiful pool. I was feeling a little intimidated until Connie greeted me at the door like a long-lost friend and cooed tenderly over Brian. She picked him up and led me out to the pool where Karen rose to greet me with a fierce hug and a firm kiss on the lips.

Connie is a lifelong runner and Karen a dedicated swimmer so they both looked terrific in their bikinis. The healthy good looks of their early 20s had matured into something even more interesting in their early 30s. Motherhood had given Connie the tits she lacked in college and Karen had also filled out a little, though neither was carrying any excess.

In addition, there were three young women in swimsuits around the pool and they came to be introduced.

"Brent," Connie said, "these are my law students Allison, Terri and Rachel. Don't try to argue with them, or they'll rip you apart!"

Allison was holding Karen's boy, Teddy, a dark-haired wiggler with his mother's eyes and bossy tone. And Terry held Connie's 4-year-old girl ... curly, sweet and calm. I introduced Brian and his cherubic face and blond mop immediately made him the center of a circle of adoring women. Karen demanded to be the first to hold and kiss him and I could tell she was smitten. Then she handed him over to Connie and pulled me aside.

"Hidden motives are at work here," she whispered, sqeezing my hand. "These three are some of Connie's best students, but they're also desperate to have babies. Connie tells them to wait until after law school, but she also brings them to her house so they can play with her little one. Today they each have a toddler to crush on!"

And that's how it worked. Allison, Terry and Rachel swam and played with our kids while Connie, Karen and I lounged in the sun, drinking ice tea, talking and watching the fun. Rachel wound up taking care of Brian and I could see she had a serious case of baby-love, attending to his every whim and hugging him often. And after he got over his first shyness, Brian thought she was wonderful.

Connie had apparently mellowed over the years. She still teased, but her gentle jibes had none of the bite I remembered from college. And once she noticed my gaze wandering over her fine, full tits and she grinned and arched her back to show off her improved chest. That's something she would never have done in college!

Karen hadn't mellowed at all. She was the same brave, fiercely opinionated woman who had stolen my heart ... and other body parts. My heart rose in my throat the first chance I had to study her lovely face. There were some fine lines at the corners of her big brown eyes, and her thick brunette hair was carefully dressed. But otherwise she seemed like the same girl I had lost years before.

Or ...not entirely. A small town girl, her swimsuits had always been average ... neither too revealing nor too concealing. But today's bikini lifted and displayed her large tits and I could see her nipples poking through the thin fabric. That was another change. Years ago her nipples had been flat and had taken a lot of teasing to bring to attention. Now they were standing up on their own. And her swimsuit bottom matched the small top. A quick glance showed no evidence of pubes between her legs, where she once had a thick mat.

Time passed, the toddlers tired and Connie's students took them in for naps in one of the guest rooms. The girls lay down with the babies to help them get settled, while Karen, Connie and I tiptoed away. Then Connie left to deal with something in the kitchen and Karen took my hand.

"Come with me," she whispered, leading me upstairs.

She took me to a bedroom suite overlooking the pool that was clearly hers from the suitcases on the floor. She closed the door.

"Now for MY hidden motive!" she said, putting her arms around me and pulling me into a deep, searching kiss.

Ginny and I have a C+ sex life, hampered by the time limits of my job and her newfound career. The sex is great when we have time, but we rarely have time. So I was not exactly reluctant when Karen started tugging at my swimsuit. Then I remembered.

"Hey," I said, pushing her away slightly. "Won't your V-V-S ruin everything?"

She frowned and nodded.

"Yeah, it ruined everything with my husband, Mr. Missionary Position, but I've been thinking of ways around it, and I know you'll like my plan," she said, giving me a quick smile.

I didn't know what Karen had in mind, but it was sure to be very, very sexy. I felt guilty about cheating on Ginny, but pushed that out of my mind. Making love to Karen again was a dream come true even if she couldn't take my cock. But I wondered how I could satisfy her when her pussy and clit were off-limits.

"Don't worry about a thing," she said, reading my mind, "just follow my lead."

First she pushed my swim trunks down my legs and I stepped out of them. She took my stiffening dick in one hand and cupped my balls with the other.

"Mmm nice," she said softly, stroking my dick. I was fully hard by this time and she inspected me closely, running a fingertip slowly around the head of my cock before tickling my opening. Her other hand gently rolled my balls back and forth exciting me even more.

In the old days Karen never did anything slowly, especially anything sexual, but now she seemed determined to take her time. She leaned her left shoulder against me while continuing to gently play with my works. That gave me a chance to unhook her top and pull it off her breasts. I reached under her arm and cupped her right breast, beginning to stroke her nipple with my thumb. Her nipples were darker and more prominent than before and this one responded by quickly growing hard. I gave it a gentle pinch and she looked up quickly.

"Yeah," she whispered huskily. "Do that."

So I began alternately stroking and tugging on her nipple, which soon stood out half an inch as if begging for more. Karen lowered her head, took my right nipple in her mouth and began to suck. I sighed with pleasure. Few women ever paid any attention to my nipples, but she was one of them, knowing how it turned me on. Whenever she was riding me cowgirl-style or sucking my dick, her fingers always started teasing my nipples. She looked up at me.

"I wish you had been there when I was nursing. I used to daydream about you sucking my milk."

I groaned, terribly aroused by the thought, and my dick pulsed in her hand.

"I think about you soooo much and how we used to fuck ... especially since I got V-V-S and can't anymore," she said. "I have dreams about us fucking and I wake up so horny I can't sleep."

Her mouth returned to my nipple and her eyes watched my face as she alternated sucking, licking and biting me gently. Whenever she sucked or bit me especially hard, I groaned and pinched her nipple hard and felt her groan, too. We did that for a long time and just as my abused nipple was starting to get too sensitive, Karen switched sides and started working on my left nipple. Naturally my left hand took over tweaking HER left nipple. Slowly she stroked my dick, now hard as a steel bar.

Stopping abruptly, she pulled me down for a long, soulful kiss, then led me to the bed where she pushed me down on my back. She knelt between my legs and in one motion took most of my dick in her mouth. I felt my dickhead pressing against the back of her mouth, then with a quick, smooth push she took it down her throat! I groaned loudly and concentrated on not coming.

She raised her head and I felt my dick sliding slowly out of her throat, out of her mouth, until only the head was held by her lips. I groaned and gave a quick thrust, trying to spear myself back into her mouth. Slowly she slid her mouth down my dick until I felt resistance at her throat. Then quickly she took me the last two inches, her lips sliding again to the base of my dick. She did that a third time, and a fourth, and I knew a fifth time would see me filling her mouth with sperm. She knew it too, watching my face carefully. She let my cock slip out of her mouth and gently squeezed the head until my orgasm receded.

Karen then kissed her way slowly up my belly and chest until she was lying full length on me and we were kissing mouth to mouth, our tongues wrestling languidly back and forth. My hands stroked her long, smooth back and cupped her full ass, still covered by her bikini bottom.

"I almost made you cum," she said, "then I remembered my plan!"

She jumped off me and off the bed and sent her bikini bottom flying. Her pussy wasn't bare, but her dark pubes were trimmed very short. She got a bottle of lube from a suitcase and stepped up on the bed. She stood straddling me and looked down at me intently. The inner lips of her pussy glistened with moisture.

"You're going to fuck my ass, deep and slow, then ... ... harder and faster," she said, her chest heaving with excitement. "And when I'm ready I'm going to watch your face while you come inside me and THEN ... while you're filling my ass ... when I can feel your dick jerking ... just touching my clit should make me cum!"

It was Karen who added butt sex to our bedroom menu years before, first asking me to finger her ass when I ate her, escalating after a few weeks to full-fledged ass-fucking. I certainly enjoyed anal, but something about that forbidden kink really turned her on, especially when I came in her ass. She would get so aroused that just brushing her clit would send her over the falls. I didn't know if her plan would work, but I was eager to try.

Moments later Karen was on her back, her ass at the edge of the bed. She hooked her arms under her knees to pull her legs back and spread them wide, giving me free access to her ass. Her pussy looked nearly normal, only slightly red and swollen, but I knew the slightest touch could be painful.

I dripped lube into her crack and used my fingers to spread the slick stuff up and down. Then I covered a finger in lube and gently pressed the tip against her asshole. My finger penetrated a half-inch until she reflexively clamped down. A second later she relaxed again and I continued slowly sliding into her butt. Soon my finger was buried in her ass so I pulled it halfway out, coated it in fresh lube and pushed it back in.

In and out, more lube, in and out. Karen was panting with arousal as I slowly, gently added a second finger to the first sliding in and out of her tight ass.

"Don't stretch me any more," she panted. "I really want to feel your dick!"

So I quickly lubed my throbbing dick and pressed the head against her asshole. She held herself motionless while I pushed steadily against her tight ass, then harder.

"Yes, YEEES!" she moaned, "PUSH!"

Suddenly, the head of my dick popped past the tight rim of her ass and was inside her. Karen threw her head back and groaned with arousal.

"AhhhhHHHH!" DON'T STOP!"

I kept pressing and my rod slid steadily into her ass until finally I was buried in her to the hilt. She squeezed my invading member once, twice with her ass, still pulling her legs wide.

"Ohmygod that feels BIG!" she gasped, "Now out ... ... careful ... don't touch my puss."

Slowly I pulled back and my glistening dick slid out of Karen's ass. Then I added more lube and slowly I pushed back in. She breathed hard and sweat glistened on her forehead. Then out again, more lube and in and ... something broke my concentration. I looked up, startled to see Connie's face peering at us through the half-open door. I was sure Karen had closed it!

"What now?" flashed through my brain. "Does she know Karen planned this? Will she stop us?"

But I didn't stop, I couldn't. I could only stare down at my dick sliding slowly in and out of Karen's ass while her best friend stood a few feet away, still in her swimsuit, staring transfixed.

In and out slowly, adding more lube, her ass gripping me like a fist, so TIGHT! And Connie was a couple of steps closer, her wide eyes fixed on my dick now sliding out of Karen's sweet ass. Connie took another step. All Karen had to do was turn her head and she'd see her friend's stunned face and wide blue eyes.

"My GOD!" Connie said quietly, but not so quietly that Karen didn't hear. Her ass clamped down hard on my dick and she turned her face towards Connie. Their eyes locked.

"You ... two ... are ... the HOTTEST thing I've ever SEEN!" Connie whispered hoarsely. Karen just stared. I stood motionless waiting ...

Slowly, Karen licked her lips. Then she spoke.

"Come here!" she commanded.

Connie took two steps and was standing beside me, her left arm touching my right. I remained motionless, my dick half-buried in Karen's ass. The two women stared intently at each other.

Then Karen let go of her leg and her hand darted out. Her fingers slipped unerringly into the crotch of Connie's bikini and she gasped and lurched against me. I looked down to see Karen's hand moving inside Connie's bikini and guessed from the angle she was pushing a finger into her friend's pussy. Connie gripped my arm with both hands and sighed as she felt herself penetrated.

"We can't!" she whispered, but there was no strength in her voice. And the next sound she made was a long, shaky moan of pleasure -- "Aaaaaahhh!" -- as her head swung loosely forward.

Looking down past Connie's fine, full tits and her flat belly I could see Karen's hand working on her friend's pussy, moving slowly in and out. A faint squishing sound told me Connie was already wet.

I reached behind Connie, unhooked her top and pulled it off. Then I put my arm around her and took her tit in my hand, kneading her firm flesh and tugging at the hard little nipple. She moaned again and Karen's finger fucked her faster. Connie was now thrusting her hips in a steady rhythm. She spread her feet to give Karen more room.

Connie moaned steadily, her groans coming closer and closer together as Karen finger-fucked her pussy and I abused her tit. Then she began gasping and cried out, and her whole body convulsed.