We went into her house and she led the way up the stairs to Jennifer’s bedroom. Jennifer, Nancy’s 18-year-old daughter was sitting on a chair at her computer, crying her eyes out. She was wearing a pair of work-out shorts made of gray cotton and one of those tight sports bras that cris-crossed in the back and looked like a halter top when girls wore them around the sports fields without an overshirt. (Brandy what’s-her-name, the women’s soccer star gave impetus to that fad when she peeled off her shirt upon winning the World Cup a few years back. ) The bra was black with the Nike swoosh on the front between the breasts. I couldn’t help but notice that even in the confines of this constricting garment, Jennifer seemed to have a larger set of breasts than her mother did. Oh, shit! What in the hell was I thinking? I could actually feel a thickening between my legs…. a reaction to a 18-year-old girl? Damn! I was more of a dirty old man than I had realized. I took a good look at the girl sitting in front of me and realized she was a prime piece of sexy soon-to-be-a-woman and smiled inwardly at the thoughts I was entertaining. Nancy went and stood behind her and pointed to the screen. I moved to where I could see it and was really shocked. The screen was filled with a picture of a teen-aged girl lying on her back on her bed with her knees up and her legs spread wide. Between her young thighs was a perfectly bald pussy, gaping at the camera. Beside her on the bed was an older woman, also naked, with a huge pair of distended breasts with dark brown aureoles and nipples. And the way she was sitting allowed the viewer to see that her pussy hair was a dark, dark mass of curls. “Now, hit ‘next’” Nancy instructed Jennifer.
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Jennifer cried even harder but slowly lifted her hand to the mouse and clicked on ‘next’ to bring up another picture. This one showed the older woman fingering the clit of the young girl as the girl arched her back and seemed to be in ecstasy. “Next!” commanded Nancy. And Jennifer continued through a slide show of eight or ten pictures of woman-young girl sexual activity. There were pictures of fingers being inserted into the young girl’s pussy. There were shots of a fat thumb shoved deep inside her shaved and wet cunt lips. Another shot showed the older woman sitting above the young girl’s face with her dark-haired pussy crammed down on the lips of the girl. Another showed a classic ‘69’ maneuver with both females sucking on each other’s cunts. The final shot was a gynecological photo that pictured the older woman’s hands spreading the lips of the young girl’s cunt as a rivulet of sticky, female cum slid out from between them. I was personally amazed at the size of the girl’s cunt hole, but said nothing at the time. “Enough” said Nancy. “Turn around to face us. ”Jennifer complied and sat there on the chair, shoulder sagging and sobs wracking her small body. Nancy went into a monolog about suspecting that Jennifer had been looking at porn pictures on the ‘net and when she discovered her today, was outraged that the pictures all seemed to be of female-to-female activity. In my mind I was a bit curious as to why this upset Nancy so much – if Jennifer had been looking at pictures of cocks being slid into pussies would that have been ok? But I didn’t have the balls to ask Nancy at this point.
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Nancy told me that she was terribly distressed that Jennifer might be gay, and that she wondered exactly what could be done to help her avoid all the social discomfort that might come with such a choice. I asked Nancy to sit down on the bed and asked if I could pose a few questions to Jennifer. Nancy agreed and I knelt down on the floor in front of Jennifer’s desk chair and held both her hands in mine. “Jennifer, honey, I know you kids think of me as your grandfather sometimes; and you’ve always been able to come to talk to me whenever you had any oddball questions that you didn’t want to ask mom or dad, right?”Jennifer nodded, but continued to sob. I continued. “Now, tell me a few things. How long have you been looking at pictures on the net like this?”“About two years,” Jennifer mumbled between sobs. “Since you were about twelve, then, right?” Jennifer nodded and I pushed on. “Have you looked at other pictures? Pictures of men? Pictures of men and women together?”Jennifer blushed all the way down to her chest around the sports bra and mumbled something in reply. “Speak up!” her mother ordered. “I looked at everything at the beginning. Men, women, animals, vampires…. but I like looking at the women together best of all. I’m not gay. I just like to look at women being nice to women,” she cried out between a shower of tears.
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“I didn’t mean to imply that you were gay, Jennifer. I just wanted to know what sort of things you look at. Animals, huh,” I laughed. “How did that make you feel?”Jennifer looked up at me with this sly, little glint in her eye and said, “I couldn’t believe there was such a thing until I actually saw it. Women with dogs; women with ponies; women with snakes; women with real, full-sized horses. It fascinated me, I guess, to wonder why a woman would do that sort of thing. ”“Well, there are lots of things women do in this world to find a level of satisfaction that they don’t otherwise have. Would you believe that I know a woman who used a huge, green, lumpy cucumber one time to make love to herself?” And I looked over her head at Nancy who was almost jumping out of her skin.
“A cucumber? Wow! I never thought of that!” Jennifer replied. Her mood was changing now and she was no longer shaking with sobs. “Well, dear girl, we simply have to find out why you are looking at these pictures in the first place; and secondly, we need to know why the pictures of women and girls make you feel better than pictures of women and men,” I continued. “Move over here beside your mother, so we can be a bit more comfortable,” I urged her. She stood and moved to Nancy’s side of the bed and I took a second to look at her lovely, lovely, long legs blending upward into the tightest teen-aged ass I can ever remember seeing. The work-out shorts did little to hide the fact that either she was wearing no underwear at all or else it was a thong…a teen-ager wearing a thong?She sat down on the bed and cocked one leg underneath her and appeared to be relaxed. “Am I going to be in trouble, mom?” she asked Nancy.
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“Not if you are honest with me and Mr. _____ about what you’ve been doing here in your room on that computer,” replied her mother. Jennifer visibly relaxed even more and I took notice of the swellings at the ends of her breasts. Her nipples must be quite large, I found myself thinking, to be that visible in a sports bra made of Spandex-like material. “Now, tell me, Jennifer, how do pictures of women and girls together make you feel?” I asked her in a very conversational tone. “Honestly? Well, I get very, very excited; I itch between my legs; I sometimes get wet down there; my … my … (and here she gestured at her breasts) … get all tingly and swell up. ” She mumbled this last with her face down toward the bedspread and sort of picking at the laces on her sneakers. I reached over, untied her laces and pulled the sneakers off her feet in such a quick motion that she really didn’t have time to react. “There,” I said. “That ought to make you more comfortable. Take off your socks, too, why don’t you. ”I caught Nancy’s look of surprise and then another of realization…. she looked at me questioningly and I just nodded my head in an affirmative manner and continued with my discussion with Jennifer as she pulled off her white socks and threw them onto the floor. “So, you’re telling me that you get excited, sexually, over pictures of older women and younger girls together, right?”“Yes, I do, Mr. ______, but I don’t really understand why.
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I never did anything like they show in the pictures. ”“Never? With no one? Did you ever touch yourself like in the pictures?”“Never with anybody else…. well, one time, when Kara and I were alone, I looked at her … her … ““Pussy. ” I interjected here. “Yes, her pussy; am I allowed to say that, mom?” Jennifer asked Nancy with trembling lips. “Of course, dear; anything that will help us understand what you are feeling is ok to say out loud. We’ve all heard the words before, so just use whatever comes to mind. ” “Well,” Jennifer continued, “I looked at Kara’s little pussy and how puffy it got when I touched it; and she looked at mine and touched it and I couldn’t believe how good it felt when somebody else’s hand was touching me. ”“So you’ve touched yourself before?” I asked. “Yeah, since I was about 11, I think. I touch and rub and finger myself almost every night when I go to bed. And sometimes in the shower with the soap, too. I wash my breasts (looking at Nancy for approval) and then I wash between my legs … my pussy (said with some satisfaction) and it feels so good when I do. Is that a sin, mom?”“Not really, dear,” Nancy murmured, hugging Jennifer’s shoulders. “We all do it sometimes.
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Even I do it in the shower. ”“Mom! Really? You touch yourself? Do you make yourself feel good? I mean really, really good?” Jennifer excitedly asked. “Yes, honey, I make myself feel so good that I explode inside sometimes. You know what that is, don’t you?” Nancy continued. “An orgasm,” Jennifer almost shouted, pleased that she knew the word. “Right,” said Nancy, stroking Jennifer’s shoulder, “I cum … that’s the word for it. When you get so excited that you feel like you are going to explode, that is called cumming. Have you ever made yourself cum, honey?”Jennifer got so red I thought she was holding her breath; but she simply whispered, “No, mom; when I get that excited it scares me and I stop. I’ve always wondered what it would feel like to keep on going, but I’m afraid it’s going to hurt so I stop and calm down. ”I touched Jennifer on the knee with one hand and allowed it to linger there as I reassured her, “Jennifer, honey, it won’t hurt. As a matter of fact, there is really very little else in life that feels as good as cumming.
Men cum, too, you know. Just like your mom says, everybody does it. I do it as often as I can. And I love it.
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”“YOU do it? But aren’t you too old……,” she blurted and realized her mistake in a second, rushing to apologize for calling me old. Both her mom and I laughed out loud at that and I reassured her again that I was not to old to cum and that I still enjoyed sex very much and hoped to continue for a long time to come. “As a matter of fact,” I whispered slyly, “I enjoy sex with somebody very special that you know very well; but I’m not going to tell you who, because that’s my very personal secret. ”“Oh, my God!” Jennifer exclaimed, “I’ll bet it’s Mrs. _____ down the block. I see her smiling and laughing with you sometimes when you are on your front porch. She flirts with all the men on the block. And her tits are huge!” Jennifer realized what she’d said and tried to stumble an apology to her mother for saying “tits” but Nancy just shushed her and told her to use any word she wanted. “Well, Jennifer, I’m not about to tell you if it IS Mrs. _____ or if it ISN’T. That’s my secret. And it will not be revealed until I think you ought to know,” I told her. My hand had begun a small circling motion on her thigh and her mother was rubbing the back of her neck and shoulders. Jennifer was much more relaxed now and asked us, “So, if I decide to go all the way when I finger myself next time in the shower, it is OK? I won’t do anything wrong? I won’t hurt myself?”“Not at all, sweetheart,” murmured Nancy, “I think it would be good for you to let go once and for all and find out how good it can feel. ”Jennifer’s hand had surreptitiously (she thought) slipped into her lap where her one leg was cocked under her and the tips of her fingers were resting on the top of her mound.
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I could tell by sneaking small glances, that she was applying just a little pressure to make herself feel good. “Now, let’s get back to the pictures, Jennifer,” I began. “Do you think you would ever like to try something like you’ve been looking at? I mean, you and an older woman touching each other and making each other feel good? Would you try it if you had the chance and knew you were not going to be hurt, and that no one would ever find out?”There was a good 30-second lapse in conversation as Jennifer screwed up her pretty little face in concentration and thought. When she finally opened her eyes, she had obviously come to a conclusion. “Yes, I think I would like to try some of the things I’ve seen,” she slowly whispered, almost to herself. “But I would be very specific about how I would do it. ”“What do you mean?” I asked. “Well,” and she glanced at her mother in some embarrassment, “she would have to be attractive – no ugly old woman – and she would have to have a big, hairy … uh … pussy, you know, not shaved or trimmed. Oh, God, this is so embarrassing!” and she hid her face in her hands. “Jennifer, honey,” her mother murmured. “I understand exactly what you mean. If you are going to try it, then it ought to be exactly as you see it in your fantasies. I can understand everything you’ve said. Would it surprise you if I told you I approved of this little adventure? Would it surprise you if I told you I have someone in mind who might be able to help us out?”“Oh, my God, mom! Do you really? You wouldn’t mind if I tried it one time? You wouldn’t get mad or think I’m crazy or queer or anything?” Jennifer burst out. “Not at all, sweetheart.
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Let me confess that I have always had the thought that I should have tried this at least one time before I married your dad. I’ve always regretted that I never had the courage. But you know your grandma; she would have had a heart attack if she had ever dreamed I thought such thoughts. We would have spent two years in church, confessing MY sins over and over an over. ”This brought a laugh to both Jennifer and Nancy and they smiled at each other. I thought I had an inkling as to what Nancy had in mind, but I wasn’t sure. I continued the conversation with Jennifer, giving Nancy hints as to what I was thinking. “If we brought this woman here to your room, Jennifer,” I began, “you would be relaxed and would try anything she wanted to try as long as it did not hurt you?”“Yes,” she murmured“And you’d be willing to give her the same treatment that she gives you, to make her feel as good as she might make you feel?” I said, while looking directly at Nancy for understanding. “Oh, yes, I would,” Jennifer breathed, and I could see an entirely new plan forming in both Nancy’s mind and in my crotch. Would it work out? Could we pull it off?.
