This lesbian matchmaking service that Lynne had gotten me involved in was paying off big time, not only in dollars for me and her but also in sexual partners for me. The latter is much more important than the former because I really do not need the money. Until last night, I only had one “match” who was April.
Lynne calls it a “match” to disguise the fact that her “matches” are really clients and that she is in fact running a lesbian escort service. I had no idea that there would be a demand for such a service, but Lynne assures me there is and she hooked me up with Ann last night.
If anyone wants to know how all of this started, they can read my two previous stories about my involvement in lesbian prostitution.
Lynne described Ann as being very different from April. For one thing she was not a domme, for another she was not wealthy. So she could not pay as much for the “match.” Lynne and I will split the $200 fee fifty—fifty. We both made a hell of a lot more money off of April, but then she can afford it and she was very demanding. I spent two evenings with her as her subby little slave playing mommy—daughter one night and teacher—student the other night. Both nights were fun and sexually satisfying but there was something that I did not like about April despite the fact that she is a beautiful woman. Frankly I do not think she is a particularly nice person. She strikes me as being a very selfish bitch which I guess is fine as long as she is willing to pay big bucks to have sex with me. She did get me off in a big way both nights.
Ann had only a few hours to engage in some bisexual lust with me because her husband was out of town and she dropped her kids off at her sisters. I am assuming that hubby does not know about her desires and we had to do it at my apartment because she could not afford a hotel room.
Lynne had described her as being in her early 30s which made her only couple of years older than me; on the small side, maybe 5’4″ which contrasts with my extreme height for a woman, but that was okay with me because I like small women. She is very slender with rather small breasts, which was also okay with me since I’m not really into big breasts although mine are full and fortunately proportionate to my height and weight. She described her hair and short and mousy brown, while my hair is also brown but it goes down my back and it is wavy. Lynne also described her as being attractive, not beautiful but attractive. She also prefers vanilla sex and has a passion for cunnilingus both giving and receiving. Now that was certainly all right with me.
She arrived at my apartment exactly a 6 pm. She needed to leave by 10 pm to pick up the kids. So that would give us a good 4 hours.
When I opened the door to invite her in, a look of total panic swept over her face and she just stood there frozen. We knew each other. She is married to a banker that my firm does business with an we have met at several social functions.
She turned to walk away and I called out “You might as well come in and talk about it. The damage has already been done.”
She turned back to look at me and then followed me inside trembling and obviously shaken.
I sat her on the sofa and got her a glass of wine which she started gulping.
Sitting down next to her I said, “Ann. I can assure you that I will not mention this to anyone. What we may do together is nobody’s business but our own.”
“If anyone ever found out,” she wept. “My marriage and my family would come to an end.”
“Well no one is going to hear anything from me,” I replied. “I certainly do not want anyone to know that I take money from women who want to make love to me. Lynne may call it matchmaking but others might call it prostitution. It would destroy my professional image in the community and it would also hurt my business.
“Why do you do it?” she asked. “You don’t need the money.”
“I do it because I get to meet beautiful women like you who happen to enjoy sex with other women. Believe me. It is a lot better than the bar scene,” I explained.
By now she had gulped down three glasses of wine and was beginning to feel no pain. She was also beginning to relax.
She smiled at me and said, “You know, ever since I found out you were gay, I have been really attracted to you but I was too afraid to let you know.”
“Frankly Ann,” I replied. “I have always found you attractive but I do not put moves on married women. It’s bad for my reputation. But now that I know that you like other women I’m getting a little excited and my pussy is starting to get a little damp.”
She just smiled at me so I leaned over and kissed her gently on the lips, she immediately returned the kiss with a surprising degree of aggressiveness which I liked. We were soon embracing each other and playing tongue duels. Her hands went to my breasts and began massaging them through the light cotton fabric of my tight tank top. I was not wearing a bra and my nipples became hard very quickly. I slipped a hand inside of her halter dress and gently stroked her tiny breast until her nipple got real hard and she let out a soft moan.
She broke the kiss and looked into my eyes, “I am sorry my breasts are not bigger. I really like yours. They are so nice and full and firm.”
“Don’t worry Ann,” I whispered back at her. “I like small breasts.” As I pulled my tank over the top of my head and undid the string to her halter exposing quite a lovely little set of A cup tits with puffy little nipples that I could not resist sucking on while she gently played with my own breasts.
My hand went under her dress and my palm touched her warm inner thigh. Her legs opened immediately inviting me in. I softly stroked up one inner thigh and down the other as we returned to kissing and licking each other’s necks. Lynne says she likes her sex gentle so gentle it would be and I kind of liked it that way too as a pleasing alternative to the rough sex and domination that I experience with other women.
Her hand went under my denim mini and immediately touched my cotton covered pussy.
“My God you are soaking wet,” she proclaimed, breaking a kiss.
She rubbed me a little and then removed her hand and placed her fingers in her mouth.
“Oh Jesus,” you taste good too she remarked and quickly put her hand back under my skirt.
My fingers touched her nylon covered pussy and she too was wet.
“Let’s kiss and rub each other to a couple of really nice orgasms before we get completely undressed and go into the bedroom,” I suggested softly and her fingers began rubbing me more ardently has her tongue rammed its way into my mouth.
My fingers began to furiously rub her clit while my lips moved down to her delicious little puffies.
She started moaning and groaning, and I could feel her lithe little body tense up. I took her to the brink and held her there for several moments. Her fingers on my pussy went still as she closed her eyes and arched her back.
All of a sudden she let out one really horrendous scream and began to quake in my arms. I continued to fiercely rub her clit driving her through yet another orgasm accompanied by the same loud scream. Fortunately my apartment is sound proof.
I continued rubbing her clit through her panties and sucking on her left nipple to see if I could get one more out of her and sure enough I did but this time she completely collapsed into a puddle of quivering jelly.
I let go of her and she curled up on the sofa in the fetal position and continued to shake for a while. I took the opportunity to stand and remove my skirt and panties.
Her eyes opened and focused on me. “My God you are beautiful,” she whispered. Then all of a sudden she looked really sad and said, “But I didn’t get you off.”
I just smiled down at her and said, “Not to fret. We still have plenty of time and remember, you are paying me and Lynne so that you can get off.”
“Please don’t think bad about me,” she pouted. “It’s the only way I can satisfy my lust for other women. I can’t go out to the bars. People in town know me.”
“Anne let me try to explain something again,” I went on. “I don’t work for Lynne because I need the money. I do it because I get to meet beautiful women like yourself and frankly I get quite a sexual charge out of knowing that someone like you would pay good money to let me get her off.”
“Well you did a really good job of it,” she replied with a smile on her face. “I have not cum like that in years.”
“Hubby doesn’t do it for you?” I queried.
“Rarely,” she frowned. “I usually have to fake it.”
“What about Lynne’s other girls?” I asked.
“They are pretty good, but not as good as you,” she said.
Then she looked closely at me.
“Julie you have no hair on your pussy, just a little on top,” she proclaimed.
“Yes,” I replied, “I like to keep it bare. More stimulating that way.”
“Oh God,” she said. “Can I lick it?”
“Of course you can,” I replied. “Follow me into the bedroom and get out of that dress.”
Unlike the living room which was awash with light streaming through the sheer curtains of the patio door, my bedroom was dark. The shades were drawn preventing any light from coming in. I lit four candles on each of the bedside tables, lifted the comforter, slid in and invited her to join me which she eagerly did. We faced each other with our bodies pressed together and began kissing. Then she pushed me on my back and began to slide down. I stopped her and said, “Let’s talk a little first before we get into it again.”
“Talk? Talk about what?” she asked in disbelief.
“You,” I replied. “Like how often do you avail yourself of Lynne’s services?”
“About once a month or maybe once every six weeks,” she answered back. “It depends on Steve’s travel schedule. Why do you want to know?”
“Because it turns me on,” I said fingering my own pussy. “When did you start with other women?” I asked.
“Well I was a freshman in college. It was my roommate. Somehow she got us some booze and we got drunk and we wound up doing it,” she explained.
“And you liked it?” I pressed.
“Yes,” she replied.
“Did you and your roommate do it again after that?” I pushed even further.
“Yes,” she mumbled. “But we also did guys too.”
“Had you ever thought about doing it with another girl before it happened with your roommate?” I asked reaching into my nightstand draw to get a dildo which I proceeded to shove into my pussy.
She looked at me a little shameful and said, “Yes.”
“Did you play with yourself and make yourself cum while thinking about other women?” I went on.
“Julie? Why are you asking me these questions?” she pleaded.
“I told you,” I smiled back. “It turns me on. Now take the dildo in your hand and fuck me with it.”
She did exactly what I told her to do and that was wonderful. I was exercising my supremacy over her and she was submitting. Lynne said she was not into anything kinky, but I was definitely into control and this little bitch was submitting to me even if she did not realize it. I guess I really am a switch.
“Work that thing,” I hissed. “Work it good.”
She just sat there shoving the fake cock in and out of me while I laid back and enjoyed it having some fond memories of when I use to fuck guys. Well Ann was not a guy but she was doing a pretty good job of hand fucking me with that fake cock eventually making me cum. It was not a great O but it helped do the trick. It cut the edge off a little bit.
I pulled her to me and held her closely and kissed her gently. “Thank you Anne.”
“You are welcome,” she replied.
We laid there for a while, kissing and cuddling and fingering getting each other’s juices going while I thought about what I was going to do to her next. I wanted to eat her pussy and I wanted to see how she might respond to the strapless dildo. For some reason I was feeling rather butch tonight.
So I pushed her on her back and spread her legs. I was rather disappointed by the fact that Ann has an extremely hairy bush. I know that some women, and men too I guess, are into that sort of thing, but frankly I find it a bit of a turn off, but considering I was getting paid to satisfy her I dove right in and started licking between her labia, much to her delight. Fortunately she tasted ordinary—a little musky, a little salty, but not bad. I slid a couple of fingers inside and had trouble finding her G spot. In fact I could not find it at all.
I paused to ask, “Anne? Do you have a G spot?”
“I think so,” she muttered, “But I think it is really deep.”
“Would you mind if I put my hand inside of you to see if I can find it?” I asked with a devilish grin on my face.
“Oh God no,” she gasped. “I’m too small for that.”
“Okay. I have a better idea,” I answered back.
I got off the bed and went to my closet which contains my toy chest and got my strapless dildo. Standing in front of her, I inserted the large bulbous female end inside of my cunt and turned the vibrator button on to medium. The bulb is large for a reason. It will rarely fall out no matter how active I get. Fortunately I have had enough hands inside of me that inserting it is only a little painful and once inside the pain goes away and is replaced by the pleasure of being filled up and of course there is the wonderful vibrations coming from the fully loaded batteries.
I stood looking down at her and there was a look of intense fear on her face.
The male end is about 8 inches long and about 3 inches in diameter.
I knelt between her legs, picked each one up behind her knees and positioned the head of the dildo right between her labia.
“Please don’t hurt me,” she sobbed.
Very, very slowly, I pushed the head of the dildo inside of her a half an inch at a time causing her to moan and groan until I had about three quarters of the shaft inside of her. Then I felt some resistance. So I slowly began pushing it in and out of her, going a little bit deeper on each downward thrust.
Much to my surprise, her hands grabbed the spindles of the headboard, her hips thrust up at me, and she started to scream “Fuck Me! Fuck Me!” Which is precisely what I did for well over an hour. I found her G Spot all right, It was deep inside of her and every time the head of the dildo stroked it she had an orgasm.
I too was having orgasms. Little ones, seconds or minutes apart, and they kept building in intensity. Some how I managed to time them with Ann’s so that we could both relax for a while with the full strap on buried deep inside of her and kiss.
Eventually I reached a point of personal satisfaction so I removed the toy from her and from me, but I put it back inside of her. I worked it deep until I found her spot and caused her to scream as she went through an explosive orgasm.
The poor woman’s arms and legs were flailing around so much that I went and got the wrist and ankle cuffs, and tied her to the bed. I returned to the toy that was deep inside of her and began sucking on her clit. The combination of the two actions had the desired effect. She was experiencing multiple, intense orgasms, making me jealous that it was not me until she literally passed out.
I undid her restraints and sucked on her little puffies until she came to. I pointed out that is was almost 10 pm and she needed to go. She dressed in silence and left.
I went to bed feel pretty much satisfied.
The next day Lynne called me and complained that Ann did not get a chance to eat my pussy. I told Lynne to set up another “match” with me and Ann, and she could lick my pussy, but I said that I had a condition: she had to shave her pussy for me.
In the middle of the next week, I ran into Ann at a cocktail party given by the senior partner in our real estate firm. We went for a short walk out on the lawn where she informed me that she had never been fucked like that in her entire life and she had gotten a wax job just for me. Her husband Steve was curious about it, but she told him that it had to do with a yeast infection. He bought it. God men are so stupid.
As we walked back to the house, she asked me if I really thought I could put my entire hand inside of her. I told her I think I could, but it would have to be slow and gentle. She just blushed with a look of terrible longing on her face.
“Be prepared to pay more than $200 the next time,” was the way I ended the conversation.
Two days later, Lynne called me and said that Ann had asked for me on Thursday night. Hubby was going to be out of town on business and she could drop the kids off at her sister’s while she did some shopping by herself and took in a movie. I agreed. I also agreed to splitting the same $200 match making fee. It seems that hubby keeps Anne on a tight financial leash.
When I greeted her at my apartment door she was wearing a simple pale blue shirtwaist dress, no hose, and white sandals. I was in a tan wrap skirt, black tank, no bra, and black sandals. As I closed the door behind her, I pushed her up against the wall and immediately began kissing her which she obviously enjoyed because she kissed me right back with a considerable degree of enthusiasm. Her hands also went immediately to my breasts. So I did the same. She too was not wearing a bra. She is one of the lucky ones, she does not have to. I have to unless it’s just around the house or I want to look like a slut, but that’s okay since I have a passion for fancy lingerie and the money I made off of April sure did make a contribution to my wardrobe.
God! Why did I think of April. She wants to take me to an S&M party next week and I really do not like her as a person. So I pushed her out of my mind and turned my attention back to Ann who was quickly trying to unwrap my skirt, which I let her do.
“I get to eat you first,” she said, “You promised.”
“Fine,” I smiled back at her as I led her to my bedroom. On the way my skirt slipped off and Ann slipped out of her dress, letting it fall to the floor. She just about pushed me on the bed and then lowered her herself on top of me and kissed me deeply as her hands played with my breasts. There are some women who know how to kiss and others who do not. Ann was a kisser; a really good kisser. April is only fair, she kisses like a man, not soft and gentle like a woman.
Ann moved down to my breasts and started working on my nipples with her tongue, lips, and to a little extent, her teeth. I like the teeth part. Her hands were also busy trying to get my thong off so I helped her by pushing it down, raising my legs, and kicking it off. That’s when she descended on my pussy and did not come up for air for well over an hour. I was treated to some of the best pussy licking of my life and believe me I have had my twat eaten by a lot of women. Ann was an expert. She licked between my labia, then she sucked my clit teasing me, then she sucked on my labia, and then continued to suck on my clit because she could sense that a tremendous orgasm was building up inside of me. With the help of two finger inside of me she drove me through six astonishing orgasms in a little over an hour’s time until I begged her to stop and let me relax. She pulled back kneeling on the bed, beaming at me.
“Julia you taste so fucking good,” she proclaimed. “Oh sorry about the language.”
“Don’t worry,” I mutter coming out of it. “I like dirty talk.”
“Do you like dirty sex too?” she asked.
“Sometimes,” I answered. “Depends on what you mean by dirty.”
“Turn over and kneel on the bed,” she said. “I want to take you from behind.”
Doggy isn’t my favorite position, but she was paying for it so I assumed the position.
She got behind me and ran her tongue between my ass cheeks causing me to shutter. “If she is going to rim me and lick my ass, I will be in heaven,” I said to myself.
And that is precisely what she began to do. Her tongue gently swirled around my anus before she began pushing it inside of me. Then she put two fingers in my pussy and her thumb on my clit while her tongue kept fucking my ass hole. That did it. The first orgasm seemed to come out of no where and hit me like a rock, followed immediately by a long build up to yet another orgasm that I thought was going to break my back.
“Stop! Please stop!” I gasped and fell flat faced on the bed, heaving and gasping for air.
She cuddled up next to me and began licking my neck. My hand slid down between our bodies and I gently stroked the soaking wet front of her panties and almost immediately her body went rock hard and she screamed through an intense orgasm. It must have been the anticipation while licking me.
When she was through, I got up and got us a bottle of wine and two glasses. We cuddled on the bed sipping our wine, exchanging kisses and stroking each other giving each other tiny but oh so satisfying little Os.
I paused for a minute and said, “Ann. You are a lesbian.”
“What?” she asked with a look of surprise on her face.
“Annie,” I replied. “The way you made love to me, you have to be a lesbian.”
She looked at me seriously and said, “Please don’t call me Annie. Steve calls me that and I hate it.”
“Do you hate your husband?” I asked.
“No. I don’t hate him,” she replied. “I just put up with him for the sake of the children.”
“Do you enjoy sex with him?”
“You asked me that the last time,” she responded with a tinge of anger in her voice. “No I do not like sex with him.”
“What about other men?”
That got no response.
“See. You are a lesbian.”
She put her glass down on the nightstand and began to cry. I held her in my arms and rocked her back and forth.
“You are right,” she blubbered through elephant tears.
Recovering, she gasped, “Julie is it possible to love another woman and be in a romantic relationship that is filled with love and caring?”
“Oh please Ann,” I responded. “Not me. This is strictly business. I already have a lover.”
“I know you do,” she replied. “I was just asking in general.”
“How do you know?” I asked curiously.
“Well I’ve seen you with an older woman at social functions and the two of you look so happy together,” she went on to explain. “I also asked Lynne and she says your lover is Eden but where is she?”
“She is in Paris for the summer on business,” I replied.
“Do you . . . Ah . . . rent yourself out when she is around?” is asked meekly.
“Not so far,” I answered truthfully.
“So why have you started doing it now?” she pressed me.
“Because I have certain sexual needs and I do not want to create any emotional entanglements,” I responded emphatically.
“When does she return?” Ann asked.
“In a month,” I answered.
“So I can have you a couple of more times before she returns?” she asked desperately.
Then I made a really big mistake. I said, “Ann. If you swear never to say anything at all to Lynne, I would be willing to see you anytime and not charge you a cent.”
She looked absolutely stunned.
Realizing the error I had just made, I wanted to shut down the conversation so I pulled off her panties and began lapping at her cunt until she had three really good Os in a row.
When she recovered, she poured herself another glass of wine, laid back on the bed, sipped it, and said, “Steve’s cheating on me.”
“How do you know that?” I asked curiously.
“Oh just little things like he does not want sex from me very often except for a morning blow job now and then. And the trips. I don’t think the trips are really for business.”
“So what are you going to do about it?” I asked.
“Nothing,” she replied. “Maybe he will ask me for a divorce.”
“Why don’t you divorce him?” I asked. “He’s the one cheating on you.”
“I can’t prove it,” she mumbled.
“Hire a private detective,” I suggested.
“I can’t afford one,” she answered back. “I don’t have any control over our money.”
Big mistake number two was just waiting to happen. I said, “I know a very good private detective who will get all of the evidence you need that he is cheating on you, and probably on pictures or even film, and I will pay for her services and you can pay me back from the divorce settlement. I also know the best divorce lawyer in town because I have fucked her a few times. She will understand your predicament and she will win your case for you if the detective comes up with the right evidence.”
There was total silence from her. I could almost hear the wheels turning in her head.
“If I get to keep my children, what’s it like being a lesbian with children?” she asked.
“Well I do not have any first hand experience, but I know several lesbians who are either single or in relationships who have children and they seem to be doing fine.”
“At 4 and 6 they might begin asking questions about why their mother is different,” she stated flatly.
“No that’s too young,” I answered back.
“What are the chances that I might find another woman and fall in love with her?” she asked.
“There are a lot of single lesbians in this city Ann,” I responded with assurance. “I am sure you will find one, but finding the right one might take a little while. You might have to put up with being on your own for a little while and dealing with casual sex.”
“Casual would be better than none,” she remarked emphatically and then in the tone of a little girl she asked, “Are you serious? Would you help me with the detective and the lawyer? And would you not charge me for your services.”
“Yes my Dear Ann,” I replied knowing that I had just dug a big hole that I had just stepped into. “Only don’t fuck the lawyer. She is a taker not a giver. The private dick “Ha Ha” is another matter. She is really good in bed.”
She gave me a big kiss and stuck some fingers in my pussy and then moved down to resume licking me again. About a third of a way to an orgasm I stopped her and told her to make a cone shape out of her fingers and force her whole hand inside of me. She looked at me in disbelief but did as I asked and her hand slipped inside of me with little trouble. I told her to make a fist and turn her hand around while sucking on my clit. Well it was not long before the explosions started and I was taken to a very far away place where I felt like my insides were being turned inside out, but in a good way, and I was screaming my head off with pleasure.
I woke up the next morning alone in bed with a dull throbbing ache in my pussy but a feeling of being completely satisfied.
About 10 am that morning I got a call at work from Ann. She said she was ready to meet with the private detective and the lawyer. I agreed to set things up. She also mentioned that Steve was still out of town and she could dump the kids at her sister’s. I told her to come over a 6 pm. All afternoon I was distracted from my work by thoughts of how I might explore her submissive side without hurting her emotionally. She was taking a big step and she needed a lot of support. That’s when I decided to find a way for her to meet Cassie and Mel, two very good lesbian friends of mine who have been together for a long time. Cassie is a shrink so I think I will give her some background on Ann so she might know how to properly respond.
For some strange reason I had this compelling desire to help Ann. It was clear to me that she was obviously gay and had a strong desire for other women. It was also obvious that she has submissive tendencies. While I am usually sub, I can switch and the domme in me was feeling an intense desire to see just how far I could take Ann before actually really hurting her. Then all of a sudden I changed my mind about that. She needed to confirm her lesbian nature before moving on to explore other dark realms of sexual desire and satisfaction.