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Her First Time (ff)

By PinkPocket

On a recent trip, I was able to stay at an exclusive resort property, and had late afternoons and evenings free to hang out at the pool. Every afternoon I saw a tallish, trim, long haired brunette. In my eyes, her bikini melted away to the most luscious, sexy body ever. Just looking at her and thinking about how sexy she would look naked made me wet. On the fourth day I just 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! Nevertheless, I chose a spot near where she usually sat, but back against the screening vegetation.

As I sat there, fantasizing about her, I let my hand creep up under the cover-up to massage my clit. My massaging intensified as the fantasy unfolded. Finally I spotted her coming into the pool area. She was so sexy in her French-cut bikini that I came. She chose a chair at a table maybe 20 feet away from where I reclined on a lounge, and looked towards the pool. I let her get comfortable while I slowly recovered from my orgasm.

I took off the cover-up, exposing my skimpiest bikini, and approached her. I stood closer than usual to her chair, my still-hard nipples plainly visible, and I felt that 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 have wanted to meet you. Do you mind if I join you?” 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.”

“Not at all, this is my first time here. I just chose 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’d love to have 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 decided to back off a bit: “Well, I’m not lesbian, if that is what you were thinking. I just enjoy women; everything about them.”

Pause. But no indication that she didn’t like the direction of 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, “Before I was married, guys would get very pushy and quite demanding. Sometimes it was . . . flattering and . . . occasionally, well, tempting.”

“So, your husband was your first?”

“Yes.”

“Have the two of you considered playing?” This was it. I hoped Kim would continue. Again she paused. Longer this time.

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

I took a deep breath, hoped for the best, and 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, but it never went any further than that. Well, occasionally a little bit when masturbating. I’ve always too scared to really do anything.”

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

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

“I 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 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.

I pulled my chair quite close to Kimberly’s at that point; our knees entwined. I opened my legs as much as the arms of 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. Her breathing changed; she brought her finger up between my inner lips and found my already hard and exposed clit. I let out a low “mmmm.”

Kimberly seemed to stop there; she didn’t withdraw her hand; just stopped. I scooted my butt forward 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 slowly, carefully slid it into me. It felt so wonderful and exciting knowing that this was her first time to feel another woman.

Almost 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. “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 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 feeling very horny and playful. I had not seen anyone else on my floor 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, bikini over my arm, down to my room.

Once in the room, I 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. During that kiss, 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 started moving her hands as well. I became aware of her hardening nipples, slightly higher on my chest 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. I want to make you cum – many times. And I need you to make me cum – many times.”

We stumbled over 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 wide V ending above her clit. Just then I was excited to feel her very wet slit. 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 to emphasize where); are you OK with it?” She looked into my eyes and 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. 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 juice, so I extended it to her mouth. It seemed that she took my fingers and started sucking them without thinking. It was only then that I remembered to pay attention to her hole. Taking my right hand from spreading her outer lips for access to her clit, I moved two fingers into her and quickly found her cervix and g-spot. This new sensation made her cum again in waves of thin colorless, sweet juice, while clamping her inner muscles tight around my fingers.

I slowed my tongue and fingers. Even though I suspected she would be sensitive following so many intense orgasms, I wanted to keep her on the brink for awhile longer. 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.

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

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

“You need to tell me what to do,” she said.

“Just do whatever you would love someone to do to you.” With that, Kim smiled and started sliding down, kissing as she went. She ate my pussy pretty much the same way I’d eaten hers. I’m very vocal – I love to talk during sex, so my sounds went from dirty talk to orgasm noise. She would improve with experience, but was enthusiastic and I kept thinking about this being her first time with a woman and that made me so horny that it more than made up for the small lapses in technique. When I cum, it is white and creamy. She expertly cleaned me up.

At the next cuddling break, I asked if she ever used toys. She had a vibrator – a rabbit. I then asked if she wanted to play with some girl-on-girl toys. I had two that I’m particularly fond of and said that I would love to introduce her to this part of girl-girl play. 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 that 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 of 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 and delighted to see 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. 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 it into me and coax 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. 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. And I controlled the penetration angles to made myself cum.

Kimberly enjoyed watching me cum and pinched 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 first got my end wet and told her to get down between my legs and fuck me. 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 up close “just like a cock would fuck you,” she said. I then told her to get her end wet. I positioned us in sitting position, legs scissor fashion, and slid up to her pussy. The head had no sooner penetrated her 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 both 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. 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, was this and that kind of thing permissible, and what was not permissible. We talked and played until well into the daylight hours, then went to sleep, still cuddling and smelling of sex.

End of Story