Entry Two: Hilda and I
Going straight from work we were among the earliest dinners. Service was quick and efficient. The restaurant was modest and good, the type of place I like going to with a guy who doesn’t need to impress me. Sometimes, on a first date I’ll sit through a hundred dollar dinner and manage to act appreciative. If the guy needs to impress himself, I’m certainly willing to be a good sport. But since college I’ve always had enough income myself that an expensive dinner has never impressed me.
“Hilda. You know you always stand up when someone walks over to your desk.” That wasn’t a question. “Do you know why?”
“Well, it gives me a chance to stretch, and it’s mostly habit. But I think I just like showing off my legs. And I’m so short that the guy still has to look down at me, only I’m now closer to him. Do you think I shouldn’t do it?”
I was surprised that she understood herself that well. I’d pretty much concluded that this was why she did it, but also that she didn’t know herself the reason.
“Oh, no. The guys all love it. I even like it. And you do have nice legs. Do you realize you do it with me also?”
“Karen, while I prefer guys, I like girls also. As much as I’d have loved doing it with Jerry, I’ll admit you pretty much turn me on as well. I’ve gone to bed with girls a few times, but the best times were always when we were sharing a guy between us. I think having a man watching or in the bed with you makes girl-girl sex really great.”
“Well, actually, I’ve never tried a threesome, except myself and two guys. And that was like doing it with one guy only more so. I’ve only had one female lover, and what we did didn’t feel like sex. We got naked and hugged and kissed a lot. And she did the thing I love most, rubbed my back. Even with a guy, that’s the part I like most, feeling his hands caress my body. Laura was good with her hands, but they weren’t big and strong. When I dream of being seduced, my lover always has big strong hands and knows how to use them.”
“Have you ever had a professional massage?”
“Several times. Only once with a woman, because it was almost a waste of time. But with a man, especially if he has me get completely naked, I’m just about in heaven. My ideal lover would do that to me first. Let me get naked, admire my body without pawing my breasts right off. Then lay me face down on the bed and work on my back for a good long time. If he wants, I’ll spread my legs slightly exposing myself to him. In fact, I hope he want my legs separated. The masseurs don’t ask you to do it, but if you don’t, they eventually make you open up while working on your legs. A massage that doesn’t include your inner thighs isn’t much of a massage. And giving him access to your inner thighs naturally exposes you crotch.
“By the time you turn face up, you’d feel unnaturally prudish not allowing your legs to fall open. The half dozen different masseurs I’ve had all treated my front differently. One wouldn’t touch my torso at all. Just my face, arms and legs. I think I actually turned him on and he was afraid to show it. I met him once later in the club bar and asked him about his technique and he admitted he was a bit new and still had trouble dealing with beautiful women. It was such a sweet answer, even though I believe somewhat calculated to please me. But he melted my heart.
“I’ve never had a masseur use my body the way most lovers do. But I have had some intimate encounters. Except for the one man, the others all massaged my stomach and waist, hips, shoulders, and thighs, meaning the side of their hands repeatedly touch my vagina opening. It happens when I’m face down as well. But, though fleeting, it seems more significant when you’re showing yourself to him. Basically all five men touched my pubes. And though necessary and almost accidental, I loved it every time every one of them touched my pussy lips. Perhaps because it was always so gentle and undemanding. When a lover touches them, if he hasn’t taken his time with the rest of my body I usually feel something like ‘well, here we go again’. I’m not saying I don’t like being penetrated. In fact I love it, especially when my lover takes his time first. But other than the fact that it gives him so much pleasure, it not my favorite part of making love. With my best lover, it’s lying face down while he works on the small of my back with those beautiful strong hands of his.”
“Oh, Karen. You make it sound so wonderful. I’ve made love a lot of times for a girl my age. But I think I’m still in the mode of not thinking much about my own pleasure. I probably spend too much effort just trying to please my partner. If he wants to fuck me the second he gets my clothes of, I not only let him, I even encourage him. I don’t think I’ve ever had an orgasm. I suppose I’ve yet to get much pleasure from a prick. Mostly I just love being naked with a guy and being whatever he wants me to be.”
“You’re doing it wrong. The guy may think he wants coitus immediately, but if you slow him down and make it last a half hour, he’ll love you for it afterwards. To a certain degree most guys want to please their partners. If you want him to play with you for a half hour first, and let him know how much you like it, he’ll be all the more appreciative when he finally ejaculates inside your pussy. At least most guys will. I guess you have to feel any guy out, usually while he’s feeling you out as well as feeling you up. I bet you love having your breasts squeezed almost any time?”
“Oh yes! Don’t all girls?”
“Well, no. Maybe big breasted girls like yourself always do. Which is why I assumed you did. With tits my size a girl sort of grows up shy about things. Sometimes a guy gets me so horny and excited, usually by massaging my back, waist and fanny, that I forget how small I am. Then I’m often surprised at how delightful it feels to find myself lost in his big strong hands. When a guy rushes things or maybe even thinks my tits are where he should start things like he would with you, well, I try not to flinch. But at best I’m just putting up with it.”
“Gee. I’d guess that makes for problems. Guys grab my “knockers” or “jugs” first thing. And I love it! It is one of the best ways for getting me in the mood. Of course, maybe I don’t ever really get in the mood since I don’t orgasm. But when a guy touches my nipples and all, I certainly want to give him as much more pleasure as possible. I guess I get compliant more than excited.”
“I know the feeling. When you just want to do anything for your lover. In fact you want him to make demands just so you can make sacrifices for him. A guy can get me in that mood. But not by squeezing my breasts.”
In spite of running at the mouth, I still managed to finish my light supper rather quickly. The restaurant was now almost filled, and it was obvious they’d like to use our table for a second setting. Anyway, neither of us felt like having desert so I paid our bill, left a tip and we left. Since Hilda lived with her parents and my apartment was nearby it was the obvious place to go. I don’t remember Hilda even asking me where we were going. She just walked next to me paying no attention to our route. I think she’s so used to letting her boyfriends decide such things that it felt natural for her to follow someone else’s lead without questioning anything.
By way of my special ability, I knew that she assumed that any man she was willing to sleep with would be nice to her and look after her interests. So far she hadn’t had any bad experiences with men. Either she was lucky or she just bought out the best in men. I was not surprised but not all together happy with the way she so quickly placed me in the same dominant role as she would a male lover. I was six years older, and taller. But I still like to think of myself as small and cuddly and appreciative of a man’s protection, if only from too many lonely nights. When I go out with a man, I like to have doors held for me, I like him to take care of the bill without discussing it, I like my chair held for me and my jacket. There are all sorts of things I want done for me because I’m a woman even though I can really do them myself just as easily as he can. Even at business luncheons I like the men to treat me like a girl and not just one of their equals.
————–
Even with Hilda, I could never be a butch in a lesbian relationship. Anyway, I’m so skinny, and Hilda so voluptuous, that although I’m four inches taller, we probably weigh the same. She’s certainly stronger than I am.
When we arrived at my apartment, she followed me inside without asking any questions, like if I had any roommates. But she did exclaim about how much she liked it when we entered. Then she turned to me and expressed the same question I’d been asking myself.
“Are we going to become lovers?”
“Hilda, you’re such a sweet thing. In spite of what you think, I’m not an old hand at this. In my only previous experience with another woman, I was the sweet young thing, she my mentor. I’m not sure I can be the dominant type you want me to be. I know I’d rather not be. If you want to try being equals, I think I’d like that. So tell me, do you like being naked as much as I do?”
The obvious invitation did not have to be repeated. We quickly got into a race to see who could strip the quickest. Hilda found our race funny, and I found her laughter infectious. Hilda, was just as pretty naked as one would expect. But then, her usual choice in clothing never left much to the imagination anyhow. As usual, I was glad to get out of my bra and throw it’s embarrassing thickness somewhere out of sight. Sometimes I like to slide slowly out of my panties giving my lover a show. But that didn’t occur to me and anyway, we’d both pretty much jumped out of them. Hilda’s blonde garden was almost as invisible as if she had shaved completely. Her nearly naked pubes made her look even younger than she was, in spite of her earth mother breasts.
I’m usually suspicious of a first time lover who claims to feel no disappointment upon seeing my tiny tits, especially if he’s only seen me previously in a padded bra. But it was obvious that Hilda found my diminutive ant hills as delightful as I found her generous melons. I’d told her that I didn’t like men grabbing them right off. But I didn’t flinch when she did exactly that. And for some reason, I liked it when she touched them. There we were standing, facing each other, both of us ignoring the most luscious set of mammary glands any man could ever hope to handle, while she played with my merely adequate ones. Playboy would never understand. I certainly didn’t.
Hilda and I didn’t technically become lovers, because we never touched each other’s genitals. When we talked about it later, we both admitted that we preferred reserving the folds between our legs for the enjoyment of the male sex. We did kiss and hug a lot, and probably even touched our pussies together without any special pressure applied. We stayed naked the whole time we were in the apartment. Around midnight, we left, and I drove her to her parents’ house. She told me the next day that she told her mother she’d been out with a guy so her mom wouldn’t have to worry about her being out so late without a male escort. Hilda’s mother was as naive as she was!
Entry 2.1: — Jim, Frank, Tom, Ted, and I
While I was writing about my recent experiences with Hilda I commented about having doors held for me. That reminded me of a business trip during my second year with the company. I went to the west coast with two managers ten and sixteen years older than me. At the client’s site we had worked in different areas. That evening I went with Jim and Frank to dinner where unexpectedly we met several of the men they had been working with. As we were no longer on company time, I’d dressed the way I would for a date. In fact, being out of town I sort of even over did it. Or, in the way of female fashions, under did it. When Jim met me at my door and saw the way I was practically spilling out of my dress, his jaw dropped. It was exactly the reaction I wanted. I had nothing against having affairs with men who weren’t my immediate managers so I didn’t care in the least if my outfit wound up getting me a bed partner. If the guys wanted to cheat on their wives, that was their concern. And if it didn’t end up leading to sex, well, I’d probably have an even better time just flirting with them.
The two men we bumped into, of course, had no way of knowing who I was. When introduced my name meant nothing to them. As they were all on a first name basis already I was just presented as Karen, they as Ted and Tom. These two men were both much younger than my coworkers, not much older than me. And neither one of them could take their eyes off my tits! Ted immediately assumed I worked for an escort service. I did my best to make Tom come to the same conclusion. Tom was the only single guy there and hopelessly involved with his present girlfriend.
Ironicly, this was exactly why he loved what he concluded was my status. His girlfriend was ying-yanging him, and he pretty much knew it. She’d been free with the sex when they started dating and up through the engagement, but she had started finding every excuse in the book now that he was publicly committed. With my special ability, I still can’t know what a third party is thinking. But it was clear that he knew what she was doing while not wanting to admit it. He had no idea why she was doing it, except perhaps as some perverted form of testing. In my opinion, whatever the girl thought she was doing, she was also just being nasty. The idea that was forming in Tom’s head was that a nice professional like myself might be the solution to his problem. Another girlfriend, when already engaged, wasn’t.
As I realized his intentions, I resolved to myself that if I did get him in bed, not only would I give him the relief he needed, but I would also show him that whatever his girlfriend had provided in the way of entertainment during the earlier part of their romance, it wasn’t anything so special that he should put up with her present behaviour. Given the opportunity, that was one engagement I wanted to personally destroy. Just before deserts were served, Tom made his excuses and went to use the men’s room. A bit later I also got up for the same reason, timing it so that I intercepted him in the hallway.
“Tom. Can I tell you in private that I love your eyes?”
Men don’t expect such comments from a woman and this reinforced his notion that I might be looking for business. For the past hour he’d been trying to think of some way to proposition me. I was certainly giving him the opportunity!
“Well, you have beautiful eyes too. In fact everything about you is beautiful.”
“Really? And I thought you were only noticing one thing about me. Or should I say, two things. They’re not really very spectacular. It’s mostly just the dress. It pushes me up and out and makes me look bigger and higher than I really am. When I actually show them to you, you”ll be dissapointed.”
“You’d show them to me?”
“Well, it’s sort of expected of a girl like me. In fact, I usually give peeks away for free. I enjoy it. But I think this is probably a bit too public. Besides, I’m not your date at the moment.”
“Ah, are you available tomorrow?”
“No, but I am later tonight. Aren’t you going to ask me what I charge?”
“What about Frank and Jim? Which one are you with anyway?”
“Both. Jim’s the one who picked me up. But our arrangement is only for dinner. I should charge extra for that. Parading around like this is going to make me awefully horny tonight if I don’t line something up. Are you interested?”
“God, more than you can imagine. I hope I can afford you, because I sure want you awefully bad.”
“Tom, I’ve already told you that I want a man between my thighs tonight very badly. And I’ve already earned my quota for the evening. After I’ve given you all the pleasure I can, I’ll let you decide what you want to pay me. But remember, if you go too cheap, it might affect the chances for an encore. Could you ask for a better deal than that?”
Of course he couldn’t! If he was willing to settle for a one shot he could have me for free. He almost said as much then thought better of what he’d almost said. It would have spoiled things. I told him that my arrangement included a room in the hotel where I can entertain. l gave him the number and told him to come up as soon as possible. Then he returned to the table while I continued my unnessary trip to the lady’s room. When I returned to the table I ignored Tom and Ted and lavished my attention on Frank and Jim, exactly the way a women being paid to be decorative would be expected to behave. It was all I could do when the five of us parted company to discourage the interest I’d instilled in Frank and Jim. Fortunately they chaperoned each other. If either one had gotten me alone a proposition would have been forthcoming. It was also fortunate that our rooms were on different floors. Both men planned to masturbated back in their rooms.
I’d barely closed the door when Tom knocked. I let him in and asked him to unzip the back of my dress. Naturally he did what almost every man does, cupped my tiny tits in his palms. But at least he was gentle about it. I kept slipping out of my dress until I was standing there completely naked. The rest of my dress was pretty revealing of my real figure. The skin tight waist and fanny were showing off the real me. Unfortuantely, sitting down at the table, this aspect got no attention while my ficticious fantasy chest created by a dress designer drew all eyes.
As I laid bare the best part of my figure, his hands slid down my front and explored my meadow of female hair. Before he got too far between my legs, I turned in his arms, pressing my nudity against his clothes, letting his hands possess the roundness of my fanny. Fortunately he enjoyed my posterior and for a while it was almost as good as the massage I always hope to be seduced with. I wasn’t really being a prostitute because he hadn’t paid me. Nor did I have any intention of letting him. But for the time being, I had to pretend I was. If he learned that I was a coworker before making love to me, I was pretty sure he wouldn’t go through with it. Sex with a woman doing it for fun was closer to being unfaithful to his ungrateful finacee than he intended.
So playing my part, I had to accept whatever he wanted, including his manipulation of my breasts. I had to even make myself enjoy it. But I loved it much more hugging him while he squeezed my buns, the one part of my body that I always want molested. In fact he did it so well, and for a long enough time, that he got me over the hurdle and could have then played with me anywhere without annoying me. I know my problem is silly and can’t help it. And when a man solves it for me, eventhough always only temporarily, I’m very grateful. But not knowing me Tom didn’t know that he was playing me perfectly. The result, however, was that I didn’t have to try to give him a good time. I couldn’t help it. I undressed him and began sucking his manhood.
“Oh that feels wonderful. My girlfriend won’t even touch it. No girl has ever done it like that. Aren’t you supposed to use a condom?”
“Too late!” I said picking my head up from his tool. “Once I touch it with my lips, there’s no reason to stop. In fact, I hope you don’t have anything because I’m going to let you do it to me the way you would with a girlfriend. By the way, I was just tested and I’m clean. You can even pretend I’m not on the pill and you’re trying to get me pregnant. I’ve heard that actually trying to get a girl knocked up is the most beautiful kind of love making there is. But that means you actually have to finish in my pussy. You can do other things first, anal sex or whatever. But you have to ejaculate in my baby maker.”
“Wouldn’t you want me to wash up in between if we have anal sex first?”
“It would be nice of you. But you’re the boss. Do my small tits disappoint you?”
“Karen, they’re smaller than I expected, and even more beautiful. I love female tits. And yours are very feminine. Size doesn’t make tits better. Especially when a guy gets to see them. There should be a law passed allowing you to never have to cover yours anywhere. Hiding them is an unnatural act. I can’t say that of most women. Of course, the way you were dressed for dinner, you weren’t exactly hiding them. But burrying such perfect beauties under a bra and sweater would be a shame.”
Maybe he only wanted to please me so that he could buy my pussy on a regular basis. But no boyfriend has ever done a better job of pleasing me. I don’t know who was doing the pleasing when it came to coitus. We just seemed to lose control inside each other. It’s not unusual, and it’s a beautiful pleasure, for me to surrender myself to a lover who’s doing a good job fucking me. But it seemed Tom was lost in a need outside both of us. The feel of a man responding to need the way a girl does when she’s in complete surrender, when I’m also giving myself to him the same way was rather awesome. I don’t remember any anal sex. My fanny wasn’t sore, but it often isn’t afterwards. Mostly, I was just off in a never-never land of pleasure, hardly aware of the individual things we were doing to and with each other. At one point I felt him ejaculating inside me and wondered why I was taking the pill when I could be making a baby with this wonderful man. Sometime later, it may have been an hour, the spell subsided enough for me to realize that I was on my back, my lover limp but still inside me as well as much of his come, and there was a small puddle under my fanny. When he got up I’d start to find that puddle annoying. But then, with my lover still inside me, it felt heavenly. The weight of his relaxed body was flattening my tiny tits between us. And that pressure I loved!
“What time is it?”
“Don’t know. Oh. Twelve-thirty. Does it matter?”
“No. Do you realize we’ve been fucking for over three hours? Are you really free all night?”
“Yes, all night. Three hours? That was quite a performance, stud. But I knew that without looking at the clock. My body knows it even better than I do! At one point, when you were ejaculating, I was wishing I wasn’t taking the pill. Of course I was thinking of you as if you were my husband, a man who’d stay around and be the baby’s father. Such a wonderful dream it was! You know that girl doesn’t appreciate you enough?”
“What?”
“The girl. I heard about what she’s doing to you. And I wanted to show you that whatever she gave you in the way of pleasure when she was giving you pleasure, wasn’t anything special. But instead you gave me more pleasure than I could ever imagine.”
“How did you hear anything about it?”
“Oh, from several of the girls who work in verification. After we were done with the Cadence problem, we went to lunch together.”
“Karen, I thought you were a prostitute. What are you?”
“A programmer here on a business trip. You don’t think they’d let Jim and Frank come here without someone technical who really knows what’s going on, do you? Those two are too high in management to be able to stay current. But I wanted you to think I was a professional. Would you have let me seduce you if you knew I was doing it for pleasure?”
“No. I would be afraid Jane might find out.”
“Jane’s no good for you. Until she finds a female lover she’s not going to be much good for herself either. Can’t you recognize the characteristics of a girl trying to convince herself she’s hetrosexual? She thinks if she binds herself to a man, she’ll learn to like it. So you got sex while she was landing you, but none once it wasn’t necessary anymore. What she gave you in the beginning was more mercenary than what you could have purchased on the street. More because most street walkers actual like sex with men. At least sometimes. Anyway that analysis is what most of the women you work with believe.”
“No one else has ever told me that.”
“Who would? Only a lover would dare.”
“So you became my lover so you could tell me? Is that why you ‘seduced’ me?”
“No. At first at dinner I didn’t even realize who you were. Tom’s a pretty common name. Actually you started turning me on the way you kept staring at my tits. All four of you were doing it and all four of you were turning me on. It was just that I felt I was responding to you more than to the other guys. I’d already decided I wanted you to fuck me tonight before I realized you were the Tom they were talking about. But that was when I decided to let you and Ted continue thinking I was a bit of fluff that Frank and Jim had hired from an escort service. Several times they almost spilled the beans by asking me something about work. But I always managed to not hear them, and get back to some other topic.”
“My god! Karen, you are fantastic. Not just as a lover. That goes without saying. You may be the best lover in the world for all I know. Compared to anything I’ve ever experienced before in bed I’d have no trouble accepting such a judgement about you! But even your manuevering was wonderful. You’re probably even a fantastic engineer!”
“You’d better believe it. What happened tonight was probably as much you as me. Maybe we just have some chemistry that only works in combination. I’ve certainly never experienced it before. If anyone had ever asked me I’d have said I was a great engineer, and a good lover.”
“Would you marry me if I left Jane?”
“Of course not. We only know each other in bed. But you’ll have to leave her, and find a normal girl if you’re ready to settle down. I’m not. But any time we’re in the same city and both free, I’d be glad to have an encore of what happened tonight. In fact, if you want and are up to it, right now would be a fine time for a repeat performance.”
My fingers around his member could feel that it had become as hard as ever. Our second time, and third time that night were both fantastic. In otherwords, nothing like the first mind blowing experience but still quite wonderful. The next morning, when we caught our return flight, Jim and Frank could tell by the smile on my face that I hadn’t spent the night alone. In fact I even confirmed their suspecisions. Sometimes girls like to kiss and tell too. Even if they only have guys for an audience.
“Jim, Frank, I’m in love! It’s a good thing you guys are taking me home, because if I stayed here I wouldn’t be able to stay away from him. And I’ve promised myself to keep playing the field for years still.”
I love to talk that way with guys. Jim and Frank weren’t “taking me home”. I was taking myself home. If any man, ex-lover, friend, brother, father, had tried to influence my decision to leave Tom behind I would have quickly put him in his place. But I love the feeling of being “taken care of”. And these two, though not even friends, got an even better thrill acting like they were my protectors. Because of the age difference and their marritial situations they loved this fantasy much more than the senario the previous evening when they were trying to imagine themselves getting in bed with me. In fact, except for being married, an affair with either man was quite imaginable. As a professional, almost their level and not reporting to either of them, a descrete proposition probably wouldn’t be considered harrassment. If either of them made a play for Hilda they’d be risking their job, reguardless of how she reacted.

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