I’m a femme lesbian who works for an investment-banking firm in Chicago. In my line of work it is hard to meet women like myself. After my girlfriend and I broke up for the last time, I became very lonely and bored. I was 36 years old and single for the first time in a long time. At first I thought that I would love my freedom, but this euphoria didn’t last very long.
I was lonely, and eager to find a woman like myself. I hit the bars with some friends but I wasn’t finding what I was looking for. I called Christine, an old girlfriend of mine, and we spent a weekend catching up and spending the night together at a hotel downtown. It was great to see her, and the sex was fantastic, but she had a girlfriend and I didn’t want to create any drama. Apparently they were in an open relationship, but I was looking for my own partner.
Like me, she was a very successful businesswoman with a lot of contacts. She gave me the card of someone she met when she was in Los Angeles on business. An escort, she said, someone who had posed for Playboy and only entertained women clients. I was a little insulted at first, but then I saw a photo of her that she kept in her purse. This girl was a 10 — 27 years-old, strawberry blonde, dark tan, amazing body, big blue eyes, and an incredible smile. Christine told me about the weekend they spent together at a beach house she rented in Malibu. It sounded incredible, worth every dollar of the $10,000 (!) weekend rate she charged. She was mostly a fitness model now, but had an escort business on the side. And she was 100% gay.
I took the card home and looked at it from time to time for the next couple of months. To say that I was intrigued was putting it mildly. I developed a lust for this woman, someone I had never met, and it was driving me a little crazy. I began surfing the web, looking for her photos, which didn’t take long, since she had posed for Playboy a few years ago and was on a few “fitness babe” websites as well. She had such a nice smile, which drew me in. The thought of her legs wrapped around mine made my pussy so wet I couldn’t believe it. I took out my vibrator and lay on my bed and brought myself to orgasm after orgasm, wasting a whole Saturday afternoon that I had set aside to catch up on work. I called Christine again. She assured me that everything was on the up and up, so I finally got up the courage to call her. I left a message on her voice mail and a few minutes later, while I was getting my things together to the gym she called me back.
“Hi, is this Ann?”
“Yes,” I said. “Hi Amanda.”
“Hey,” she said. “You’re Chris’ friend.”
“Yes. We’ve known each other for years.”
“She’s told me a lot about you. I’m so glad you called.”
“She told you about me?”
“It was all good, believe me. She talks about you all the time.”
“We’re good friends.”
Suddenly, I felt a little light-headed and sat down on my bed.
“Are you okay?”
“Just a little nervous. I’ve never done this before.”
“I understand. But you called me, didn’t you.”
We spent the next hour talking about different things. She told me that she likes to get to know her clients before she meets them and she did a good job of making me comfortable. We made plans to meet for the weekend in a month. No house, in Malibu, though–she would have to fly to Chicago.
I was still a little concerned about the price. It seemed like a lot of money. Way too much. I hadn’t taken a vacation in years. I was so busy at work. When I broke up with my ex, we had to cancel a trip that we’d been planning. I know, poor me. But I felt like I needed to treat myself before I began my fresh start. I had a lot of money saved. I had made good investments. Now it was time to splurge.
I spent the next couple of weeks getting glammed up. I got highlights, regular manicures, pedicures, facials…and I spent a lot of time at the gym. The week before Amanda arrived we met again for another lovemaking session. Christine liked it rough, so I pulled her hair and buried her face in my pussy, giving her orders, rubbing my cunt across her rock hard abs until I came. I was ready.
I took a half-day at work so I could meet her at the airport. She was easy to spot. Amanda walked briskly down the airport corridor with her luggage, wearing a short black dress and blazer, open toed-sandals, flashing that incredible smile. As she approached I had to catch my breath, she was even more stunning in person. I felt guilty looking her over like a piece of meat, her legs, her hips, boobs, ass, and a really pretty face. I could see heads turning as we embraced and she said my name. I felt like I was in a dream.
“Great to finally meet you, Ann.” She said.
“Finally,” I said, embracing her and giving a kiss on the cheek. “I hope your trip was okay.”
“It was fine.”
We stood there and looked at each other.
“I feel like we’re already friends,” she said.
We walked to the car and I held the door open for her and she got in.
In the car I paused for a second and looked at her. She smiled and leaned in and kissed me on the mouth.
“Let’s have some fun,” she said.
I had set her up in a boutique hotel near my apartment. I figured that we would spend the night there and if all went well; go to my place for the rest of the weekend. I could tell that Amanda was impressed. She loved the room, which was really a suite, with a large tub and a king-sized bed. We sat and talked for a while. I had ordered champagne for the room and as we drank it, I could feel myself finally relax and loosen up. She was very interested in my job and asked me a lot of questions. Finally we held hands and moved closer to each other on the sofa. Then we kissed. It was incredible. “What do you want to do Ann?” she asked.
Our kisses became more passionate now, and I could feel her hot, sweet breath on my face. I sucked on her tongue and she smiled. ‘Mmmm…,” she said. “Now we’re getting somewhere.”
“I’m still a little nervous,” I said.
“It’s okay,”she said. “I’m here for you.”
She pulled me even closer and kissed my neck and behind my ears. I was in heaven. She buried her face between my breasts and breathed in.
“Mmmmm…,” she said. “You have no idea how hot I’m going to make you, do you?”
“You’re making me even more nervous.”
We laughed and then she stood up and took my hand and walked me to the bed. We took off each other’s clothes and lay down and began to kiss. Amanda got on top of me and grinded her pussy into mine. She sucked my tits and then glided her tongue down my belly and kissed my pussy. I moaned. She looked up and flashed that incredible smile.
She kissed my pussy again and then flattened her tongue and softly licked around my pussy lips I spread my legs wider and put my hands through her hair. She spread my pussy lips apart with her fingers and licked harder and sucked on my clit. She put her hands under my ass and buried her face in my pussy, nibbling and licking on my clit as I moaned and bucked under her. She looked up at me and then took my hand and squeezed it as she fucked my pussy with her tongue and then licked again and I came, falling back on the bed as my back arched and I nearly fainted with pleasure. She moved up to me and I took her gorgeous face in my hands and kissed her and we wrapped our legs around each other and squeezed. “That was amazing,” I said.
We kissed again and then held each other.
“You came so hard,” she said.
“I like to eat a girl’s pussy out at the beginning. It tells me a lot about a person.”
“Sounds like you’ve had a lot of experience.”
We kissed again and began a long languorous lovemaking session. I ate her pussy from behind, fucked her ass with my fingers, rimmed her while I played with her pussy…69…I came so many times I lost count. Then we got into the hot tub and had more sex. I told her that she had beautiful feet. I took her toes into my mouth one by one, sucking them hard. She did the same. We dried off and got back into bed. She wrapped her gorgeous legs around mine and I grinded my pussy into hers and we fucked like this for what seemed like hours, having one last explosive orgasm before we collapsed in each other’s arms and fell asleep.
I had a dream that night about my first girlfriend. We’d met when we were pledging the same sorority. She was a beautiful blonde from the Upper East Side of Manhattan. She knew she was a lesbian, but was going through the motions to please her parents, knowing that once she graduated she could do whatever she wanted. The first few months of our relationship were some of the happiest times of my life. We wound up leaving the sorority and living in the dorms together. We were constantly making love. Eventually we fought and broke up; she moved in with a friend off campus, but we remained friends and then after college she moved to Paris with a girlfriend. In the dream she was fucking me with a strap-on, something we’d never tried. Someone was knocking on the door as she was fucking me. Suddenly it was Amanda in the bed with me. She was fucking me in the ass with a strap-on. I woke up. It was 8:30 am. I got up to go to the bathroom. When I returned Amanda was awake. She summoned me to the bed. We kissed and cuddled for a while and talked.
“You were insatiable last night,” she said.
“So were you.”
“You took the lead.”
” I couldn’t resist.”
I drew her closer. She rested her head on my shoulder and put her hand on my belly and rubbed it.
“So what’s on the agenda for today?” She asked
“You want to leave the bed?”
“I think we should. I might begin to bore you.”
We kissed a little more and then showered and dressed. She opened her suitcase and laid her clothes on the bed. She asked me what she should wear. This was a turn-on for me. I picked some really nice jeans and a wife-beater. I made her tie her hair back and put on flip-flops and put on just a tiny bit of make-up. I wanted to enjoy the day without thinking about having sex with her every second. I think she appreciated this. I picked out a similar outfit. We joked and laughed a lot while we were dressing and getting ready. We checked out of the hotel and put her things in the trunk of my car and then drove into town for some breakfast at a café that attracted a lot of hot women. Amanda was impressed. We spend an hour sitting and talking and girl-watching. A few times women passed and smiled at us. We smiled back. “It’s too easy,” I said. “Even when you dress down, people are staring.”
“I’ve picked up women at cafés like this,” she said.
“But women are weird. They get possessive. Sometimes I wish I could be a gay man.”
“I don’t know why I’m still so horny.”
“Do you want go to my apartment now?”
“And do what, fuck all day?”
“Now you’re just teasing me.”
I touched her knee under the table and she grabbed my hand and squeezed it.
She told me about her last relationship, a photographer she had met when she was getting her portfolio together. This woman wanted to marry her, but Amanda wasn’t ready. She said that she was attracted to older, successful women. She liked their confidence. And they were often better in bed. She squeezed my knee and I felt dizzy. I purposely steered the topic away from sex and relationships. She told me that she was saving to go back to school. She wanted to get an M.B.A. and start her own business. I didn’t press her on the details. When we were done, we took a walk through a park and sat and rested for a while. I suggested that we go shopping, and then go to a spa near my apartment.
I bought her a bracelet and a necklace and then we picked out a dress for her to wear that night when we went out for dinner. I liked buying her things, it made me feel sexy and powerful and watching her try things on in front of me made my pussy wet. She seemed very happy, almost giddy as we walked around the store, frequently touching me and taking my hand. She was so sweet and funny. We must have created a spectacle but I was past caring about such things.
After shopping, we drove back to my neighborhood and went to a spa a few blocks from my apartment. I had purchased her a temporary gym membership, but it was clear that whatever workouts we were going to have that weekend were going to take place in the bedroom. The women at the spa took our things and gave us robes. I liked this particular spa because all the women who worked there were super hot. And that day it was like entering a dream. When Amanda left for her massage with Lana, a beautiful petite German woman who had given me several terrific massages in the past. I felt jealous. Karen, a tall redhead, and one of the managers of the spa, showed me to my room and told me to wait one second. I undressed and wrapped the towel around me and lay down on the table. Amanda came in wearing her robe. “What are you doing?” I asked.
“A surprise,” she said. “I’m giving the massage.”
She leaned down and kissed me on the lips. “I’m licensed,” she said.
“I arranged this last week. I asked Christine.”
“This is my gift to you.”
She locked the door, took off her robe and told me to lie on my stomach and began to rub me down with massage oil, going slowly down my back and talking time to massage my shoulders, hips and ass. I spread my legs slightly and she kneaded my thighs and calves, stopping at my feet. Needless to say, my clit was throbbing. She worked her way up again and then rubbed my arms and hands. “Feels nice,” I whispered.
She made me turn around and lie on my back. I looked up at her and she smiled.
I reached for her and she pushed my hand away. “Bad girl,” she said. Then she took the tube of oil and squeezed a generous amount on my belly and rubbed it in, giving my tits a good squeeze and then working her way down around my pussy and legs, massaging my feet again, squeezing my toes and lifting my legs up and working the oil in. Then she worked her way back to my belly and leaned in and kissed me. She looked so beautiful. She squeezed some more oil on me and then without missing a beat, got on top of me and put her leg between mine and began to fuck me. I really felt her strength as she slowly grinded her pussy into mine. I pulled her face toward mine and we kissed and sucked and licked and then she pushed me down and fucked me harder, grinding into me. I could feel her pubic hair rub against mine and then my clit and I gasped and dug my fingers into her ass and she moaned and I began to come and she fucked me harder and then we both came, gasping and holding on to each other, our bodies shaking.
Finally, we reached my apartment. Amanda kicked off her flip-flops and walked around.
“I love it,” she said. “It’s so you.”
“What do you mean by that?”
“I don’t know…tasteful, classy…I like your taste.”
She took time to look at my books and CDs, popping in my Kate Melua CD and dancing around the room. I poured us some white wine and we sat on my terrace and talked and held hands. I kept on squeezing and kissing hers.
She told me about her first trick, an agent in Hollywood, who worked on the top floor of a building in Sherman Oaks. Every Thursday afternoon for almost a year, Amanda would go to her large office in a short shirt and no underwear and sit on a sofa opposite this woman’s desk and spread her skirt and masturbate while this woman continued to make phone calls and look at her computer. When she was close to cumming she would moan and the woman would stop what she was doing and walk over to Amanda and kneel down and eat her pussy until she came. Then, without speaking, Amanda would leave.
“And what did she do?” I asked.
“Went back to her desk.”
“Hmmm…” I said. “I don’t think I could do that.”
I took her hand and pulled her up.
“I want to eat your pussy right now, though.”
She smiled and kissed me. “Okay.”
“You don’t mind.”
“Of course not.”
We went back into the apartment and she took off her clothes and lay down on my bed. She spread her legs and began to masturbate in front of me. Her body looked so gorgeous. Her skin glowed against the white sheets. I told her to rub her pussy harder and to beg me to go down on her. I told her rub harder and faster. She began to fuck her pussy with her fingers and whispered my name. She moaned and I got on top of her and kissed her. She kissed back, but then I moved my head away. I kissed her neck and then behind her ears. Then I glided my tongue down her neck and kissed and sucked on her breasts, nibbling and biting on her nipples. She moaned louder. I licked down her chest and belly and took the fingers out of her pussy and sucked on them. She was begging me now. I moved down and kissed her pussy as she writhed under me. I began to lick slowly, remembering how she made me cum so hard the day before. I took my time with her, enjoying the sweetness of her pussy juices as I flattened my tongue and licked her clit and then fucked her with my tongue as I spread her pussy lips and licked around the hood of her clit. She shuddered under me and put her fingers through my hair and I looked up and we smiled at each other and then she lay back and squeezed her breasts and whispered my name. She put her legs over my shoulders and I spread them wider and licked her harder, flicking her clit with my tongue and I could hear her breaths become more rhythmic and she moan, and soon she was moaning louder and whispering my name and I looked up as I continued to lick and saw her head rear back, her perfect body arch as her legs and her hips began to shake as she came. I kissed and licked her pussy again and then she pulled me toward her. “Oh my God, Ann,” she said. “That was so nice.”
“I’m glad you enjoyed it.”
We began kissing and cuddling again.
“Do we really have to go out again?” She asked.
“We have to eat,” I said. “Aren’t you hungry?”
“We make love later I want it to be really special.”
“It’s already been special.”
“I mean it. I have a bag of toys, my strap-on. I’ll be your slave.”
“Or maybe you want be my slave.”
We kissed again.
“I’ll have to think about it.”
We freshened up and got dressed and then I took Amanda to this trendy Sushi place in my neighborhood. She put on the dress and shoes that I bought for her and modeled them for me. I put on a little black dress that I’d been saving for the right occasion. I’d entertained clients at this restaurant before, so it was easy for me to get a private booth.
She knew a lot about Japanese food. She’d been to Japan with her ex, and living in Los Angeles had exposed her to a lot of different sushi places, so we had fun picking out different things to try. We also drank a lot of sake, which helped when the discussion turned to sex. I whispered in her ear hat I wanted her to fuck me in the ass with her strap-on. She thought that was a great idea. “I’m a little nervous,” I said. “It might hurt.”
“Don’t worry,” she sad. “I’m an expert. I’ll make you love it.”
She slipped off one of her shoes and rubbed her foot against mine. “I can’t wait to get you in bed,” she said. I put my hand under the table and squeezed her foot.
“You have pretty feet,” I said. “I love kissing them.”
“How soon can we get out of here without making a commotion?”
We raced out of the restaurant. I took her hand in mine and we walked home at a slow, relaxed pace. Just thinking about all the fun we were about to have seemed more exciting then the actual thing itself. I pulled Amanda closer to me and put my arm around her waist and squeezed her ass and then we picked up the pace. Once inside, we sat on the sofa began to slowly kiss and caress, slowly removing each other’s clothing, and soon we were ready to fuck. First we took a shower, which gave us more time to kiss and explore. I wanted to remember every inch of her, as I kissed and licked, paying special attention to her neck and shoulders, kissing behind her ears and licking them, biting her earlobes and feeling her do the same as her hands roamed my body.
We got out and dried off. Amanda took out her bag of goodies and showed me the strap-on she was going to use on me. It was long and pink and she made me suck on it before she lubed it up and attached it to the ring. Then she put the harness around herself and adjusted the straps as I watched.
“You’re going to love this,” she said.
She made me lay on my stomach and she got on top of me and kissed and licked my back, trailing her tongue down until she reached my asshole and began to eat it, licking all around my crack and then sliding one finger in and fucking me. I moved my knees up and waited for it. She entered me slowly, rubbing the cock around my asshole and loosening me up and then going in, filling me up as begged her to fuck me. Soon she was inside and we moved together. I begged her to spank me as we fucked and it felt so good through the pain and I began to play with my pussy as she fucked me harder. Soon I was cumming and it felt like it was going to last forever and when I finished I practically passed out in her arms. We slept through the night.
The next morning, as I was driving her to the airport, I had a daydream that what Christine had really done was fix us up, that Amanda wasn’t an escort at all. Or maybe that she was one, but thought that if we hit it off, we could start dating. I tried to work up the courage to tell her this as we parked and I walked with her to the ticket agent. But as we hugged and sneaked a kiss, I didn’t want to ruin it. “Call me,” she said.
“I will,” I said.