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Cindy's First Time

"Cindy discovers a new side of her sexuality"

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Author's Notes

"My great thanks go to submissivemom72. She is the inspiration of this story and The Erotic Portrait, and her help in crafting both of them must be acknowledged. Please follow her stories, she is a fantastic author."

One evening, after a very stimulating sex session without her husband, Cindy and I were lying in bed, and she was perusing my portfolio on my phone. She suddenly stopped at one particular drawing, turned to me and said, “Who’s that? She’s gorgeous?”

I looked at the art work. It was a drawing I had done a couple of years before of a 40-something model named Taylor. She was fully nude, sitting next to a pool, with one leg in the water.

“Oh, that’s Taylor,” I said. “She’s a ‘hot wife’ model. Her husband is a photographer, and she used to have artists to use the photos as reference for paintings and drawings. “

“Doesn’t she do that anymore, Cindy asked?

“No, ‘someone she knew discovered her pictures’ on the Internet. It’s a shame, because I was ready to do another one. Why so interested in her?”

Cindy turned her head a bit towards me, and said “I don’t know, but I find this picture very erotic, and sexy. I find myself quite attracted to this lady, and I seldom am attracted to women. I like this drawing a lot. I Know it sounds silly, but I think I am developing a crush on her, she’s so…I don’t know… confident, poised, and gorgeous. I guess I’m a little envious…Part of me wants to actually be her.”

Cindy’s comments caught me off guard. I did not remember her ever reacting this way to a woman’s picture. “In all of your adventures with other men, haven’t you ever been with another woman?” I asked.

Cindy blushed noticeably to this question. It obviously made her uncomfortable. As forthcoming as she had been about her many exploits, I found her reticence to discuss this aspect of her sexuality surprising, yet endearing. I did not ever remember another situation where she was actually shy.

“No,” she stammered nervously, “I have been with countless guys, but the situation has just not presented itself for me exploring another woman's body, or her mine...and it is seldom that I feel attracted to another woman...

But this lady is special, and I feel a strange attraction to her image, especially her confidence and poise while she is posing. She really is something special ….” Her voice trailed off, and Cindy looked away.

I took my hand and turned her head back towards me. “Are you embarrassed?” I asked.

Cindy nodded slightly, and yes quietly said, “Yes. I am, a little. I’m not sure why, but I am.”

“Hey,” I said, “there is nothing to be embarrassed about. Two women making love is one of the most beautiful, erotic things in the world. It’s okay to admit that you find a beautiful woman attractive.”

Cindy looked up at me with her beautiful eyes, and gave me a deep kiss. “Thank you for comforting me, and for sharing this with me. I’ll have wicked fantasies of Taylor whenever you and my husband aren’t around.”

For days I kept thinking about this exchange between Cindy and me. The art of Taylor obviously touched deep something in her, a hidden sexual desire that even Cindy hadn’t realized before. Because I cared for her very deeply, I wondered how I might help fulfill a fantasy of hers (and mine) without making her feel embarrassed or on display.

I was traveling back out to Cindy’s area shortly after our conversation, and with her husband’s permission, was going to treat her to a ‘date night’ with me. I made arrangements the evening I would arrive in town at a high-end restaurant, so I could treat Cindy to a special night out, with surprises. After my meetings, I went to my hotel, showered, shaved, and made my final plans for my night with Cindy.

I went to pick Cindy up at her home about an hour before our reservations. Her husband Jim opened the door and invited me inside. Cindy was apparently still getting ready. After some small talk and a quick drink, we heard their bedroom door close upstairs, and I looked up.  My jaw dropped.

Cindy was dressed in a slinky, form fitting short black dress that accentuated her beautiful athletic figure perfectly. She wore a necklace of small pearls, and long dangling earrings. She glided down the stairs in 4” black pumps that made her legs look 10 feet long. She was absolutely stunning, and I couldn’t believe I was her date this evening.

“Hi.” Cindy asked coyly, “How do I look?”

I don’t remember what I said, but I was sure it was something stupid. Cindy had an aura of sexuality about her that was intoxicating.

Jim chuckled and said, “She doesn’t dress like this that often, so please feel honored.” I just shook his hand and said, “Thanks for letting me take her out this evening.”

I finished my drink; Cindy said her good byes to her husband, who told her to stay out as long she wanted. We walked out to my rental car, when I opened the door for Cindy, she exposed even more leg, almost to her crotch.

“Careful, lover,” she said, “You shouldn’t get too worked up before dinner.” She was teasing me, and I loved it, especially because of what I had in store for her later.

We got to the restaurant in time for our reservations. We were escorted to our table, and I held Cindy’s chair out for her before I took my place. Cindy ordered a glass of wine, while I got a gin and tonic. We engaged in small talk for the most part, but the sexual tension between us was palpable. Cindy kept flirting with me throughout the drinks and the meal, making little innuendos here and there, and occasionally gliding her hand up and down my thigh. Cindy was playing with me, and I loved it.

Because I knew where our flirting was headed, Cindy and I skipped dessert and coffee, and I paid the check. We got my car, and Cindy again flashed me leg when I opened her door for her. She smiled mischievously at me, and settled into her seat. I tipped the porter, and climbed in the driver’s side, so I could take Cindy to my hotel for some adventures. Cindy kept lightly touching my leg during the drive, and occasionally flicked her fingers over my now very hard cock. She was a naughty minx this evening, and I couldn’t wait to get her back to my hotel room for her surprise.

We pulled up to my hotel, and I left the car to be parked by the attendant. I helped Cindy out and we quickly walked to the elevator that would take us up to my room. Once we got inside, Cindy pulled me towards her and gave me a deep, sensual, full tongue kiss. My hands roamed over her curvaceous ass while she held my head in her hands.

“I have wanted to fuck you all night!” she said “I don’t know if I can wait.”

The elevator stopped at my floor, and the doors opened. “I think we had better wait until we at least get into my room,” I said. “And you may want to wait until I show you your surprise.”

Cindy looked at me quizzically, but followed me down the hall. We reached my room, where I pulled out the electronic key, unlocked the door, and offered for Cindy to go in first.

“I hope you like your surprise,” I said.

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Cindy turned her head towards me, then entered the room and walked down the short foyer to the bed. She stopped suddenly in her tracks, and cried, “Oh my!” On the bed was my model friend Taylor, the woman whom Cindy expressed a sexual desire for not long ago. I arranged for Taylor to secretly come to my room while I was romancing Cindy, so that Cindy could experience another woman for the first time.

Taylor was lying against the headboard. She wore only a skimpy matching lace bra and panty set. Her eye makeup was done up in a smoky, evening style, with dark eyeliner and heavy eye shadow. Her lipstick was a very deep, dark red, which accentuated her blonde hair. She looked completely sultry.

“Hell, Cindy,” Taylor purred. “I hear you like my artwork.”

Cindy drew in her breath lightly. She couldn’t take her eyes off Taylor, and she froze, seemingly not sure what to do next.

I broke the silence after some moments. “Cindy, honey,” I said softly,” why don’t you go greet our guest?”

Cindy slowly moved over to the bed next to Taylor. She took Taylor’s face in her right hand and looked deeply into her eyes. Without a word, she leaned forward and gave Taylor a soft, sensual kiss.  Taylor responded warmly, teasing Cindy with her own lips.

Suddenly, Cindy forced her tongue into Taylors’s mouth, and the two ladies fell into each other’s arms, against the pillows.

Cindy’s hands roamed all over Taylor’s body, seductively rubbing her while still French kissing my model friend. She began to rub Taylor’s natural breasts, softly grazing her nipples and making them stand up as hard as pencil tips.

This elicited a slow, low moan from Taylor, as she was obviously enjoying Cindy’s attention to her boobs. Cindy broke off her deep kiss from Taylor, again looked deeply into her eyes, then, slowly, kissed her way down to Taylor’s left breast. Cindy pushed Taylor’s bra cup aside, and began to suck and tease Taylor’s already hardened nipple, expertly biting and licking it. Taylor’s tossed her head back, as her arousal obviously heightened.

Cindy seemed to instinctively know how to touch and caress Taylor. I was fascinated to see Cindy rocking her hip, almost as though she was humping against the air, as Taylor responded to her touch.

This was a different side of Cindy then I had witnessed before. She had always been very demure submissive with me and her husband. Now, she was a cougar, attacking her sexual prey with such ferocity I had never seen before. Admittedly, the sight of these two beautiful women was arousing me greatly, and my cock was hardening in my pants quickly.

Cindy continued her assault on Taylor’s tits to Taylor’s obvious pleasure. Cindy began to snake her left hand down to Taylor’s groin, and firmly started to run her labia and flick her clit. Taylor was in obvious heaven; she moaned and groaned while Cindy kept up her Sapphic assault.

Cindy broke off from Taylor’s now-reddened tits and sat up, unzipped her dress, and stepped out of it. Unbeknownst to me, Cindy wasn’t even wearing any panties—she had sat at the restaurant the whole time in just that skimpy dress. Cindy climbed off the bed, and repositioned herself between Taylor’s spread legs, directly in front of her engorged labia. Cindy removed Taylor’s now wet panties, bent forward, and lightly licked her first pussy…slowly at first, teasing Taylor to no end, then harder, forcing much of her tongue in her cunt. . Taylor was rotating her hips and grinding them against Cindy’s expert tongue, finally reaching her first orgasm.

“Oh god! Oh Fuck! Don’t stop, don’t stop, make me cum!” Taylor cried, all the while Cindy was furiously licking her snatch. By this time, I had my pants down and was stroking my cock furiously to the beautiful show in front of me. Cindy had moved her left hand down to her groin as well, playing with herself while continuing to taste Taylor’s creaming pussy. It was the most erotic thing I had ever witnessed.

After a few minutes of this, Taylor softly pushed d Cindy’s face from her snatch, and invited her up on the bed. Taylor gave Cindy a deep, wet kiss, enjoying the taste of her juices that were on Cindy’s lips and tongue. Taylor broke away, and slyly said to Cindy, “your turn.”

Cindy lay back on the bed, and Taylor climbed between her legs.  Cindy’s blonde, short trimmed pubic hair was glistening from her wetness. Taylor knelt down between Cindy’s legs, lightly stuck a finger in Cindy’s pussy.

“Ohhhh,” was Cindy’s reaction. She was obviously ready to be licked by a woman for the first time. Taylor continued rubbing Cindy softly, then bent down and began to lick Cindy’s labia. Cindy arched her back. From experience, I knew she was achieving her first orgasm.

Taylor kept licking Cindy lightly, a different style then what Cindy had done to her. Cindy rotated her hips in time with Taylor’s talented tongue. By this time, I had all of my clothes off, and was rubbing my cock and balls while watching them make love to each other. This was one of the few times where I could observe Cindy’s powerful orgasms from afar, save for a couple of times that I watched her husband make her cum, and he usually wanted to include me. Cindy was very sensitive to touch in the correct regions, and she could cum quickly and often when stimulated properly. Taylor was doing just that to her.

“Oh fuck, Taylor, keep licking there,” she said to my friend while Taylor licked her clit. “Oh fuck, I’m cumming, fuck, FUCK!” Taylor had secretly slipped a finger up Cindy’s sensitive ass, and the anal rimming with the pussy licking sent Cindy into another wave of orgasms.

“Don’t stop, DON’T STOP!” cried Cindy “make me cum!! More!” Taylor dug her tongue deeper into Cindy’s pussy, and inserted another finger. By this point I couldn’t hold out any longer, as watching Taylor make love to my Cindy was too much. I erupted in streams and streams of cum all over my chest and hand. I kept rubbing and, surprisingly, I came again while watching Cindy arch her back and grind her hips into Taylor’s mouth in one last powerful orgasm.

Taylor climbed away from Cindy’s pussy, looked at me, and said, “Look what we did to him!”   The ladies chuckled as they viewed my cum splattered chest and hand.  “My, my,” Cindy said in a soft voice.  “Did you save some for us?”   I just smiled at them.

Taylor got off the bed and walked over to me, followed by Cindy.  Taylor hugged me and said, “Thank you for inviting me to this beautiful lady’s initiation.”  

Cindy swirled her finger in my cum, and seductively brought to her lips while gazing into my eyes.  She wrapped her tongue around her finger and swallowed my sperm like a lollipop. “Tasty,” she said.   Taylor laughed at Cindy’s tease.

Cindy wrapped her hands around my head, pulled me close to her face, and gave me a deep tongue filled kiss.  I could taste the combination of Taylors’s pussy juices and my sperm.  She looked at me as only a lover can, and said,” Thank you.  Thank you for making this wonderful evening for me.  I cannot wait to tell Jim all about what you did for me!” 

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Written by artistman
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