Julie's StorybyLesly Sloan©
Note: this is a sequel to "Classified Ads", which is in the Erotic Couplings section.
* * * * *
Sleeping with the boss is a common way to get ahead in the business world. I slept with my boss and found a whole new life. Her name is Ann Richards and she is a top executive in our firm. Our business is export/import, and Ann is an exception in a field dominated by men. She is very bright and very aggressive. I felt lucky to get a job as her personal secretary because of my limited experience. Our relationship had been strictly business until the time I discovered her getting oral sex in her office - during regular business hours - from a man known only as "Mr. Wilson."
Ann scheduled "Mr. Wilson" for 30-minute appointments from time to time, usually under the guise of "Sales Study Planning." Even I, with my limited experience, knew that this made no sense. He would arrive at the appointed time, spend 30 minutes with her, and leave very quietly. For the life of me I couldn't figure out what the hell was going on in that office. One day I was finally overcome by curiosity - I barged into her office during one of her meetings with him, on the pretext that some very important papers had just arrived.
At first the scene in her office made no sense to me. Ann was sitting at her desk, with her chair swiveled 90 degrees to the side. Then I spotted "Mr. Wilson." He was on his knees in front of Ann, and his head was moving up and down. When I realized that Ann's skirt was pulled up and her panties were down around her shoes, it was clear that she was getting her pussy eaten. That was a shocker to me - I had heard of such things but never participated in any way. In fact, my sexual experiences were very limited. I stood there frozen in place; I was embarrassed as hell and felt like dropping through the floor. Ann was amazingly cool about things. She did not stop the oral sex session as I stood there! She simply told me to go back to my desk outside her office and that she would talk to me later. When "Mr. Wilson" left about twenty minutes later I couldn't look him in the eye.
Ann called me into office shortly after he left and told me to keep quiet about what I had seen. She threatened me with such things as getting fired and being sued for defamation of character if I blabbed to anyone. "Is that clear?", she said. "Yes, Ms. Richards", I replied. "Believe me, I won't say anything to anybody." She told me to go back out to my desk and to continue my secretarial tasks as usual.
On the surface things continued as before the incident in Ann's office, but I was very troubled. I was staying in a cheap room in a ratty neighborhood to save money. I was very lonely. Since coming to New York six months earlier I hadn't really made friends. As for social life, forget it! I went to some dances to meet men, but New York is a tough place to meet nice guys. I knew that men were attracted to my firm boobs and tight ass. When I look at myself naked in the bathroom mirror it seems to me that I have the kind of body that most men want. And I'm pretty smart besides. I should be a great catch for a man who is looking for a quality woman. The guys I met at dances seemed mostly interested in getting me into bed. They were pretty crude on dates. Usually they would play "grab ass" with me and suggest that I ought to give them a blow job. Perhaps I would have been tempted to have sex with them if they hadn't been so crude.
Speaking of sex, that's a big problem for me. I am quite horny and masturbate very often as a result. But I'm a small town girl with almost no sexual experience. It doesn't help that I come from a very religious family in which it is assumed that sex happens when you get married. The social and sexual scene in New York was something the folks back in Indiana could never have imagined. Technically, I was not a virgin. I had some sex with my boyfriend back home. But he was as inexperienced as I was, and even more consumed by guilt over "doing it" before marriage.
Here I sat in what was supposed to be the most exciting city in the world, with no friends, no sex, and masturbating at night so that I could get to sleep. After I saw Ann and "Mr. Wilson" together in her office, my masturbation fantasy changed. I used to close my eyes and imagine a "Prince Charming" sort of character who made love to me in a very slow romantic way, as I fingered my nipples with the fingers of one hand and moved three fingers of my other hand in and out of my pussy. But now I was consumed with a powerful and bizarre sexual image quite different from anything I'd experienced in the past. It was ME, rather than "Mr. Wilson" performing oral sex on Ann! I imagined kissing and licking every part of her pussy, tonguing her clitoris until it popped out of its hood, and then sucking on her clit until she came in a powerful orgasm. The taste and aroma of her sex permeated my fantasy world. It was by far the best masturbation fantasy of my life. But that made going to work and seeing Ann in the office a form of torture. I wanted to take her in my arms and then kiss and lick every square inch of her body, but most importantly her pussy.
The fact that I pictured sex with another woman was specially erotic for me. It dealt with something "forbidden." In the world I come from homosexuality is considered dirty and rarely discussed. I did have some guilt feelings and was uneasy about what might develop with Ann. I decided not to let those doubts spoil the best fantasy I'd ever had. I also fantasized about being punished by Ann for barging into her office during her session with "Mr. Wilson." She would tie me up and whip me, or spank me on my bare bottom while stretched across her lap. Somehow the idea of being disciplined by Ann excited me. These things bothered me so much that one day I asked her if I could discuss a very personal matter with her. She said it was OK to discuss personal matters with her and that she would keep all such information confidential. I came into the office and managed to tell her about my two fantasies; performing oral sex on her, and being disciplined by her. I emphasized that those images were very powerful and disturbing - it was becoming a real problem. I asked if she could give me advice on how to handle the problem. There was what seemed to me a long awkward pause. Ann finally said, "Let me think about what you told me. Maybe I can give you some good advice. I'll let you know when I have something to say."
About ten days later Ann called me into her office to discuss my "problem." "Strong sexual images are hard to handle", she said. "I'm willing to work with you on that problem because you've been such a great help in organizing and running this office. Would you like that?" I responded said that would be wonderful - when could we get started? Ann suggested that I come to her place on Friday night, after work - and cautioned me not to mention this to other people in the office. She said that we would have an informal dinner and drink, followed by a problem-solving session in her apartment. "It's fine to dress informally," she said, "but please wear some nice underwear." The implication of that last statement didn't get to me until later; I was thrilled by what she might have meant. I think that I've always been bi-curious but suppressed those feelings. I went overboard in preparation for my visit to her place; I spent 167 dollars at Victoria's Secret for a supply of very sexy bras and panties.
I arrived at exactly 7:00 PM, the designated time, at her apartment.
She lived in one of the beautiful old buildings you see in the Village. I didn't know anyone else who lived in a building with a doorman - it was quite different from the hole I was living in.
Ann greeted me at the door with a soft kiss on the cheek - it was the first time she kissed me! Rather than her usual business attire she was dressed in very soft feminine clothes. She wore a lovely silk blouse. I noticed that the top four buttons on the blouse were undone, showing very sexy cleavage. I had a fleeting thought of how nice it would be to reach in there and touch her breasts. It seemed that she wasn't wearing a bra - that excited me. She wore a lovely black bolero skirt. She said that we had a reservation at a nearby restaurant and that we should go right over and return to the apartment for our "working session."
I felt that I was on a real date - my first one in New York. She held my hand on the way to the restaurant. We were seated and chatted over drinks while waiting for the food to arrive. It was a lovely evening with a close friend - completely different than the work environment. As we chatted she occasionally put a hand on one of my knees. It could have been a quite innocent thing on her part but I hoped that it was quite a bit more. I knew what she would find if she moved that hand under my skirt, up to my panties. They were already getting wet!
Over dinner Ann asked some questions about my fantasies. Had I ever previously dreamed of having sex with a woman? "No", I said. Did I think that I would enjoy sex with a female? After a long pause, "I'm not sure. I'd like to try that form of love to see if I like it." Ann seemed to be satisfied by my answers to those very personal questions and turned to asking about my social life and whether I had found a nice guy yet. I decided to be honest, telling how disgusted I was with the social life in NYC. "Don't worry, dear", she said. "When you meet the right person you'll be very happy here." On the way back to her place we held hands again. I felt some stirrings down below. I was getting horny about my boss after a few drinks and dinner! After entering her apartment we hugged and kissed each other. In my mind before this evening I had thought it would be awkward to get intimate with Ann - after all she was my boss. Not true - it was obvious that we wanted each other.
Ann took charge, as any good executive would. She led me into the bedroom and unbuttoned her blouse. She was lovely, with firm breasts topped by long red nipples. I started to kiss and lick her nipples. She pushed me back gently so that she could remove my blouse. The expensive bra from Victoria's Secret was removed in about 20 seconds. Two women naked to the waist embraced, kissed, and sucked each other's nipples. I was falling in love. With my boss! With another woman! Crazy - but it's what happened in Greenwich Village on that September evening.
The rest of the night seemed to me a blur of passion. We were buck naked in bed with our bodies intertwined. Ann pushed my legs far apart and got her head down into my crotch. She made love to my pussy with her tongue. My clitoris is large and protrudes when I get aroused. Her tongue made circles on the clit, and then she sucked on my bud, progressively harder and faster. I came in a rush, releasing copious juices.
We were dozing in her bed about 9:30 in the morning when I realized that I had a dental appointment at 10:00 AM. "Holy shit", I yelled and started to get out of bed. Ann said sleepily, "What's the matter, hon?" Upon hearing of the dental appointment she laughed and said, "Call your dentist from the bedside phone and tell him that you've been up all night with a sick friend and that you may have to spend the rest of the weekend with her." After calling the dentist I asked Ann what sickness my friend suffered from. "LOL", she said , "Lack of Loving."
We spent most of the weekend in bed, where Ann showed me many ways of making love. Some of our most intimate moments were when we explored oral sex. Ann straddled me and used her mouth, lips, and tongue on my pussy and the surrounding area. As she did that I had her lovely cunt right above my head. I reached up with my arms around her butt and drew that steamy pleasure cave down to my mouth. I could taste and smell her sex - it was intoxicating! Then she brought out some toys. There was a double dildo so that we could fuck each other at the same time. She had a terrific collection of vibrators that could be used in almost every body orifice. It was an unforgettable night of passion.
I found it to be thrilling to have this lovely woman teaching me how to satisfy her. I felt proud of my newly acquired skills when she said nobody had eaten her pussy better than me. I loved the sex but, in a way, the softer moments when we held each other tenderly and dozed off were just as satisfying. By late Saturday night Ann decided to start working on my punishment fantasy. First, she asked me if I often felt guilty. "Yes", I said. "In my family guilt was a big thing. We were always asking God to forgive us for something."
"How badly do want to be punished?", she asked.
I found that a bit ominous; she seemed quite ready to inflict severe pain if that was what I really wanted. I was careful in how I answered the question. "I'm not sure. I suppose it depends on the person punishing me and the type of discipline. Maybe it's not punishment from just anyone that I crave. I think it's the thought of you, dearest Ann, making sure that I do exactly as you wish. That excites me."
"I'll start gently and we'll go as far as you feel comfortable, dear. When I'm applying discipline you must address me as 'Mistress'. Do you understand?"
"Yes, Mistress Ann."
Ann started the first of what she called "training sessions." The basic idea was for me to recognize her complete power over me. I surrendered to her power, accepting her dominance and taking whatever punishment she decided to mete out. (Only to someone I loved and trusted like Ann would I be willing to grant such power.)
In this first session she had me lie naked across her lap while she spanked me with a hair brush. The spanking was mild at first but increased in force. At each point in the session she said something like, "You are guilty of barging in on me. Take your punishment", at which time she administered a stroke with the brush. "Tell me when you can't take any more pain. Do you understand that?"
"Yes, Mistress. I understand."
At first the spanking was very mild. By the fifth stroke I felt a stinging sensation. At the tenth stroke I was feeling pain. I wanted to prolong the session as long as I could because I was getting sexually aroused as the pain increased. By the twentieth blow I was very close to an orgasm but had to ask for mercy.
"Please Mistress. I can't take any more!" The punishment session was over at that point. Anne spread a soothing lotion over my ass and kissed me.
This weekend I had found not only a lover but a Mistress as well!
We took the subway uptown on Monday morning, I went up to the office at 8:45, my usual arrival time. Ann had a snack at a nearby coffee shop and came into the office at her normal arrival time, 9:15.
It seemed strange to maintain the old executive-secretary relationship at work when we had been so intimate at her place. But we were very careful to keep up appearances. The only exception was when Ann got very horny. She might call me in to "take dictation" and put her hand up my skirt and play with my pussy.
Two weeks after our first date I moved into Ann's apartment. I kept the old rented room, so that I could give a different address than Ann's building. I took care of mail by renting a P.O box. It bothered me to spend rent money for an unused place but Ann laughed it off and said, "Dear that's a very small expense, and remember that you're here at no cost - other than giving me the sex I crave. I would gladly pay much more for that talented mouth and tongue of yours!"
In the Village it is very common to see lesbian couples walking hand in hand, or with one woman's arm around her partner's shoulder. We blended in perfectly. There is a whole gay and lesbian community; bars, coffee shops, movies, sex toy shops, and the rest - that cater to a gay/lesbian consumer. Most of the shops in the Village aren't much different than those in any other neighborhoods in New York. But the Village is a special place. For example, there is a store called "Lee's Transvestite Boutique" and there are five piercing parlors where you can get your nipples, nose, ears, and almost anything else pierced. One such parlor actually offers to pierce a woman's labia and insert a small metal ring there for her!
For a long time I had guilt feelings about getting involved in a "different kind of love" with Ann. It was hard to imagine what my family back home would think if they knew that I wasn't looking for a potential husband but was in a love affair with a woman. I kept those doubts from Ann, but they still disturbed me. However, in the Village what we were doing was accepted as quite natural and any doubts I had in that respect faded away - I was happy with Ann and no desire to look for a man instead. On some occasions I felt uncomfortable. For example, I was jealous if we went to a bar and some other woman made a play for Ann. We had an agreement to not let those things bother us. Still, Ann knew how much it bothered me; she made it clear to anyone trying pick her up that she was quite happy with her current sweetie.
One thing I discovered about Ann was her passion for anal sex. I was doubtful at first about having my asshole penetrated, but she persuaded me to try it. We had already taken the first step by pushing a finger in and our of our partner's anus while making love - we both liked that very much. Ann bought a special dildo at a shop in the Village that had a big selection of sex toys. This dildo was designed for anal sex, rather than vaginal sex - it was long but not very thick. Thus, there was very little risk of pain when pushing past the anus into the rectum. With the use of liberal amounts of lube she got me to accept the dildo after a few awkward tries. It was an amazing feeling to get fucked in the ass by my female lover. As she humped me I pushed my hips back against her thrusting body. Anal sex has turned out to be one of our favorite activities.
Ann wants me to do the same thing to her. I'm looking forward to that.
The balance of power in our relationship shifted over time. At first she was completely dominant and I did whatever Ann wanted. Eventually I became more of a leader in our relationship. I remember the weekend when I first took a leading role. Ann's 35th birthday was coming up. I decided to do something very nice for her, to show appreciation for what she had done for me. I told her that I was planning a special weekend and that I wanted to be completely in charge of that weekend. I said "Ann dearest, I want to take care of everything and relieve you of having to do any planning or taking care of arrangements. Leave everything to me. All you have to do is enjoy yourself."
On that Friday night I had reservations at a very nice French restaurant. We dressed up for the evening - it took a long time to get dressed because we took time out more than once for a quick fuck with my favorite dildo - all part of my careful planning! Finally we were ready to go, and I must say that we made a stunning couple. While we were at dinner a few guys whom I had hired came into the apartment and transformed it into a "fairyland"; a quite appropriate name considering their sexual orientation.
When we got back from dinner the apartment was a very romantic place; soft colored lighting, old ballads playing on the tape unit, and my birthday present on a side table that had been moved out to the center of the room. When Ann opened my present she hugged me and cried. I had purchased a piece of porcelain of the type she collected. (The shop owner assured me that it was a very fine piece when I shelled out a significant part of my savings for her present.)
I took charge of the lovemaking that night. I had her lie down on her back and spread her legs. I licked and kissed my way slowly from her lovely nipples down to her pussy. When I got to that marvelous cavern of pleasure I used my tongue on her inner lips and licked my way to her clitoris. She was so aroused that her bud was already accessible. I brought my head directly down to her clit and embraced it with my mouth. It was sweeter to me than anything I had ever tasted before. She started to moan and breathe hard. Her hips thrust upward in a spasm of desire. In response I sucked on her clit until her body shuddered and she climaxed. That night I tried every type of sex that I knew in order to give her pleasure. At one point I put Ann's legs on my shoulders; this meant that her whole lower body was accessible to me - not only her pussy but the perineum, the sensitive area between the asshole and the vagina. I planted soft kisses there; it drove her wild! When she seemed exhausted I just held her. I masturbated a few times during the night when she wanted to relax, as she watched me. That was exciting for the both of us. After masturbation I stuck a finger into my cunt and gave the finger to Ann to suck on. Her reaction - "That's so delicious, sweetie! Can I have more, please?"