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Her First Sex With Another Woman (improved)

By PinkPocket

On a recent trip, I stayed at an exclusive resort property and had late afternoons and evenings free to hang at the pool. There I saw a tallish, trim, long haired brunette. Lustfully looking at her, her bikini melted away to the most luscious, sexy body ever. Thinking about how sexy she would look naked made me wet. On the fourth day I decided that I had to meet her. I put on my sexiest pearl white bikini, with a short white cover-up and ventured down to the pool. She was not there! I chose a spot near where she usually sat, but more towards the back against the screening vegetation.

As I lounged, fantasizing about her, I let my hand creep up under the cover-up to massage my clit. My massaging intensified as the fantasy unfolded. When I spotted her coming into the pool area, in her sexy French-cut bikini, I came. She took a chair maybe 20 feet away from me, and looking towards the pool. I let her get comfortable while I slowly recovered from my orgasm.

I took off the cover-up, exposing my skimpy bikini, and approached her. I stood closer than usual to her chair, my still-hard nipples plainly visible; I’m sure I smelled of sex from my orgasm, “Hello, I’m Stephanie.” I could see the bow on her bra stretched tightly between what appeared to be perfect 34C breasts.

She looked up, with a slow smile, “Hello Stephanie, I’m Kimberly, or Kim.”

“I’ve been noticing you for the last few days and wanted to meet you. Do you mind if I sit down?” I asked.

“Please sit down,” still with that beautiful smile. I sat in the chair facing her, where our legs could touch if either moved.

Being very horny and not at all reserved, I was direct: “You look so relaxed and comfortable; this must be a familiar place.”

“This is my first time here. I just came here it to get in some relaxation and pampering,” she answered, “while my husband is away on business.”

“This is my first time here also. You are the first person that I’ve met. During the day I’ve been working, so I haven’t had time for any pampering,” I responded

“Their steam rooms, massages and manicures are outstanding . . .”

“Female and male masseuse?” I interrupted.

“I’m sure they have both,” she said with a slight laugh. “I always get a male.”

“I love a female masseuse,” I added: “They are so much more sensual and erotic.”

Kim hesitated, “I guess you aren’t married for that same reason?”

“Oh, sex with men is fantastic. I have a live-in boyfriend and our sex is amazing. But, . . . well . . . you aren’t a lifestylist, are you?”

“Huh? I’m not sure what you mean.” Kim said.

I backed off a bit: “Well, I’m not lesbian, if that is what you were thinking. I just enjoy women; everything about them.”

Pause. No indication that she didn’t like the conversation, so I added: “I sometimes want to have some no-pressure contact with a woman. Men can be very intense, especially when sex is involved.”

Kim grinned, “Guys can get very pushy and quite demanding. Sometimes it is . . . flattering and . . . occasionally, well, tempting.”

“So, your husband was your first?”

“Yes.”

“Have the two of you ever considered playing?” Again she paused; I went slightly crazy in that moment, hoping she would continue.

“Playing? Does that have something to do with your previous question about a lifestylist?”

I took a deep breath, hoped for the best, then spoke slowly, judging Kim’s reactions. “They are terms that swingers use. I’m into swinging with and without my boyfriend. Swinging doesn’t involve an emotional connection; the sex is purely recreational; freely consenting adult recreation. I’m also Bi. Bisexual, that is. When swinging, I enjoy sex with guys and girls, depending on circumstances. To be quite honest I often find the female to be the turn-on.”

“Oh,” was her only comment, but she didn’t show any signs of awkwardness.

“So, occasionally a massage from a female can lead to some wonderful recreational sex.” I said as my right hand massaged my left breast. Kimberly was thinking. Before the silence got awkward, I added: “Did you ever experiment with girls? In college, perhaps? Or think about it when masturbating?”

“I’ve thought about it, but never went any further than that. Well, occasionally a little bit when masturbating. I’m always too scared to really do anything.”

My right hand was still massaging my left breast; once again the nipple was hard and visible thru the thin material. My left hand descended between my legs. “Have you ever tasted yourself when masturbating?” Kim nodded. “Did you enjoy the taste?” Again a nod. “Well, another woman is like that, only so much more erotic and exciting.” My index and ring fingers were clearly rubbing my clit thru my bikini, and I could feel the wetness through the thin material. “Another girl just knows where and how to touch you so much better than a guy.”

Kimberly’s voice got bit huskier: “I have wondered what it would be like to feel another’s breasts and vagina.”

“When I’m playing, having recreational sex that is, I get horny faster and stay horny longer than making love with my boyfriend. Like right now, my pussy is very wet and my nipples are harder than with a guy. And I get bolder – I’ve never worn this skimpy swimsuit in full public view before; I’ve only worn it at swinger parties so that everyone can get turned on seeing me.”

“It IS very skimpy. I kind of thought you were braver than me, or . . .” she trailed off, not knowing what to say.

I pulled my chair quite close to her at that point; our knees entwined. I opened my legs as much as the chair would allow and pulled the bikini material to one side, exposing my shaved, wet pussy. “Would you like to feel me right now? Touch my pussy?” Kim was clearly excited and confused. Her mind must have been racing. “It is alright; just run your hand across it.” Slowly and somewhat hesitantly, she reached out and lightly touched my mound. I removed my right hand from my breast and wrapped it around her wrist, guiding her hand down between my legs, and positioning one of her fingers to slide up between my lips. Just that light touch on my inner lips sent my mind reeling. She caught her breath, brought her finger up between my inner lips and found my already hard, exposed and swolen clit. I let out a low “mmmm.”

Kimberly seemed to stop there; she didn’t withdraw her hand; just stopped. I scooted my butt to the edge of the chair, providing better access, and making her fingers press into me more firmly. “Please Kimberly, put your fingers inside.” Glancing over her shoulders to insure that no one was watching (I didn’t care at this point!), and making up her mind, she rubbed up and down a couple of times to get her index finger wet, and carefully slid it into me. It felt so wonderful and exciting knowing that this was her first time to feel another woman, I got even wetter.

In a whisper she said: “Oh, my, I can’t believe this.” I moved my hips up and down – if only she would keep this up for a few minutes, I was so horny, I was certain that I’d cum. My movements encouraged her to move her finger in and out slightly. I let out a long, quiet moan, mostly to encourage her.

“Oh, sweetie, you could make me cum right here.” I said with ragged breathing. “But perhaps we ought to move indoors?” I wanted to get her naked in the worst way. Kim took her time removing her finger. I again took control and guided her hand towards her mouth. At the last moment she opened it and put her wet finger inside, sucking on it. “Are you OK?” I finnaly asked.

“You are delicious,” was all she could say.

I straightened my bikini – top and bottom – took the key card out of my cover-up, stood and pulled Kimberly up. I left the cover-up behind as we walked together in our bikinis to my room. I was so very horny and playful at the same time. I had not seen anyone else on my floor all week at this time of day, so in the elevator, I looked Kim in the eyes and removed first my bra, then my G-string. The doors opened and I walked off the elevator in my heels, small bikini in one hand, down to my room.

Once in the room, I let out a laugh, immediately dropped the bikini, turned to Kimberly and pulled her in for a tight hug. Despite my highest heels (I’m 5 ft. 4 in.), I had to look up slightly into her eyes, and slowly leaned in to kiss her. She didn’t pull away. The kiss was sweet; it started slow and gained intensity as Kim loosened up. As it got more frantic, I pulled the bow tying the back of her bra, running my hands up and down her back, down across her beautiful bottom, and playing at the ties on either side of her waist. As the kiss went on, she moved her hands as well. My mind was so consumed that it took a while before I became aware of her hard nipples, slightly higher on my boobs than my rock hard ones.

“Kimberly, I need to have sex with you now! This is your first time, so tell me what is comfortable, and I’ll respect it. But, I have been so horny for you since I first saw you on Monday that I need you badly. I want to make you cum – many times. And I need you to make me cum – many times.”

We stumbled to the bed together, still kissing, now on the mouth, now around the neck, and eventually I got to kiss and suck on her perfect, firm breasts. As my hand went down to her now exposed pussy, I found closely trimmed hair. Later I saw that it was a well trimmed, dark, in a big V ending above her clit. Just then I was excited to feel her very wet slit. I was more turned on by her than I could remember. Gently, but with more speed than usual, I worked my fingers around her velvet folds until I could get one finger lightly on her clit. Her kisses became more intense and passionate. When we broke momentarily for air: “Kimberly, I want to lick you (my fingers emphasized where); are you OK with it?” She looked into my eyes and very slowly nodded.

I kept playing with her pussy as I kissed my way down, catching her strong heavenly scent before I got to her belly button. After kissing her inner thighs and lightly running my hands all over them and her mound, I extended my tongue to lick her inner lips from the bottom to her clit. Her taste instantly had me in a lustful swoon. Just then I couldn’t imagine doing anything other than drinking in her juices. She responded with a loud moan and a thrust of her hips. Every lick got better and better. Sometime later, Kim’s gyrating hips brought some sense to me and I took her protruding clit into my mouth, sucking and flicking it with my tongue. I don’t know how many orgasms she had; I was rewarded with the best juices ever, truly the most delightful I had tasted. My left hand was soaked with my own juices from finger fucking. I extended it to her mouth. Without thinking she took my fingers and started sucking them. It was only then that I remembered to finger fuck her hole. I took my right hand from spreading her outer lips and flicking her clit, and moved two fingers deep inside of her to her cervix. This new sensation made her cum again in waves of thin colorless, sweet juice, while clamping her inner muscles tight around my fingers. And that made me cum hard!

I slowed my tongue and fingers, exhausted. Although I thought she would be sensitive following so many intense orgasms, I wanted to keep her on the brink for awhile longer, but with a nervous laugh, she pulled my head away. I withdrew my fingers and made my way up to kiss her. I love my pussy smell and juice on another’s mouth and hoped that she would. Her kissing was just as passionate as ever, and to me, sweeter than before.

When we slowed to cuddling, Kimberly said: “I have never had such long, intense orgasms in my life! I never would have thought it possible without a cock.” Then: “May I return the favor?”

“Only if you want to. I had great orgasms from what I was doing to you . . . and from fingering my own pussy.”

“Will you tell me what to do?” she said.

“Just do whatever you would love someone to do to you.” Kim smiled and started sliding down, kissing as she went. She ate my pussy pretty much the same way I’d eaten hers. Knowing I was her first and feeling her excitement, made me hyper sensitive. I’m very vocal – I love to talk during sex, so my sounds went from dirty talk to orgasm noise. My racing mind focused on this being her first time with a woman, all the new sensations that she was having, and that made me so horny that it more than made up for some very small lapses in technique. When I cum, it is white and creamy; and this time, plentiful. She expertly cleaned me up, making “mmmm” sounds all the while.

At the next cuddling break, I asked if she liked toys. She had a vibrator – a rabbit. I then asked if she wanted to play with some girl-on-girl toys. I had two of my favorites with me and said I’d love to introduce her to them. I got up and went over to my suitcase in the closet, got out a dildo in one hand and the harness in the other. I said we could play with the dildo – it was much more fun than playing alone or when a guy uses it – but it was truly a lot more fun when used in the harness as a strap-on. While explaining all of this, I put the dildo in the harness and put it on myself. Kimberly was excited to see it – her first strap-on in real life. But she thought it would be a bit strange to be fucked with it. After talking for a while, she still wasn’t keen on being fucked with it, but wanted to try fucking me. I made a production of putting it on her, taking opportunities to play with her pussy as I did so. Once it was in place, I sat in front of her and sucked on it to get it wet, fingering her cunt between the straps, getting her wetter at the same time. I told her that doing the fucking was a lot of work. As much as I wanted to feel her breasts while she fucked me, I turned around for doggie, knowing that it would be easiest for her first time. I had to help her guide the cock into my cunt and coaxed her on how to thrust to get maximum benefit. Pretty soon she got into a good rhythm. Still, it wasn’t doing everything for me, so I had her stop and asked her to lie on her back. I then rode it cowgirl style. We could play with breasts, and occasionally I reached around behind and got to her clit. I controlled the penetration angles and made myself cum with another gush of creamy liquid. She came moments later, soaking the bed.

Kimberly enjoyed watching me cum, watching the cream leak out around the cock. She kept pinching my nipples at just the right times.

I promised that the next toy would make us both cum from fucking, but asked if she had any reservations about our pussies touching. She thought about it for a brief moment and said that it sounded fun. I laughed and said that it would be fun with a toy, and brought out a double headed dildo. I said that not every woman liked this toy, but it was a favorite of mine and explained/ demonstrated that it was long enough to provide maximum penetration while allowing us to rub together. I got my end wet and told her to get down between my legs and fuck me with it. She expertly spread my lips and slid it in. I told her to slowly fuck me while watching. This is a big turn on for me, and as it turned out, she got very horny from watching it disappear and appear “just like a guy’s cock would fuck you,” she said. I then told her to get her end wet. I positioned us in sitting positions, legs scissor fashion, and slid up to her. The head had no sooner penetrated her cunt than she bucked into the rest of it; our pussies instantly together. She must have tightened her muscles because this drove the dildo farther into me than ever before – not painful, but deeper. We started moving around. I reached over to massage her clit as we fucked. With my forefinger I could rub hers and reach mine with my thumb at the same time. She came within minutes; I was a split second behind. I wouldn’t have thought it possible, but the juices flowed freely from both of us. By this time the wet spots were massive.

She made no move to withdraw and I love to slowly grind on this toy after orgasm, so I did. She responded with the same slow movements. When we removed it, I stuck her end in my mouth and offered my end to her. She eagerly sucked on it. We ended by deeply kissing, tasting our intermixed juices.

When we finished, and lay cuddling, Kimberly wanted to know all about swinging: how I got started, what were the rules, what kinds of experiences I’d had, did anyone ever get jealous, what was the most erotic thing I’d done, how many guys and girls had I fucked, was this and that kind of thing permissible, and what was not permissible, and so on. We talked and played until well into the next day, then went to sleep, still cuddling and smelling of sex.

End of Story