Keeping a Family Tradition Tammy s Initiation
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The Escort (6) - Initiation free porn video
Rosie, who was my “Madame” at Marchmont Ladies, had just introduced me to the pleasures of anal sex; far from being the uncomfortable experience I had expected, it turned out to be a delightfully enjoyable way to have sex, and I couldn't wait for her to take me to the next stage so that I'd be ready to take a real cock up the ass.
But for now we were idly cuddling and stroking and it was nearly time for me to go. As I was just about to stir myself to get dressed I remembered something I had been meaning to ask her; in the excitement of our love-making that afternoon it had completely slipped my mind.
“Rosie,” I said, “I meant to ask you. You know that last assignation you gave me, the one with Mr Harris?”
“Ah, yes. The strange Mr Harris. What about it? Or him?”
“Well, you know I ended up going to his daughter's fashion show? Well, that was fine. And after the show we had a little private party; I got to have sex with his daughter, Holly, while the models and photographers fucked in small groups. It was rather hot, actually. But I was just wondering about Mr Harris. He didn't join in completely but he did watch and wank; and I thought it at the time and I've been thinking about it ever since, something didn't quite add up.”
“Well, he is a bit of an odd-ball, I agree. But what's bothering you, really?”
“The fact that he watched his daughter having sex – lesbian sex – and that he masturbated to it. And earlier, it looked as she had been colluding in some game with him; she told me he'd sit in the corner as he usually did, and she addressed him as 'Mr Harris' in a way that suggested she knew it was all play-acting. I don't know; I can't put my finger on it exactly, but I really do wonder, I suppose, if Holly is actually his daughter. But in that case, what is going on? Any idea?”
Rosie chuckled. “Oh, sweet Evelyn, you are so innocent and naïve in many ways, in spite of being such a raunchy girl who fucks and sucks men and women with gay abandon. You have such a lot to learn. Now, I'm not saying they aren't father and daughter, but if they are then we do not exercise judgement in our work here. We are paid to satisfy our clients, and they pay very well for our service, as you know. But I have learned that it never pays to question people too closely about their private lives, especially where sex is concerned. Sometimes a fantasy is so deeply ingrained that it effectively becomes a reality. Those little clues you picked up on suggest to me that the two of them are indulging some joint fantasy, which to be honest seems harmless enough. I did mention, I believe, that I'd had dealings with Miss Harris before?”
“Yes, I vaguely remember you mentioning something about that.”
“The truth is that I've had a very close relationship with her that you might find quite interesting to hear about.”
“Now you've just got to tell me,” I said, sitting up to attention now, the sheet wrapped round my naked body, my eyes pleading with her to let me in on whatever secret it was that she had.
“You need to understand that this was some time ago. Holly is, what, 22 or 23 now? This all happened about six years ago; I'll leave you to work that one out. I was the age Holly is now and just starting to get the business going. It was a tough time, no doubt about it, building up a client base with discretion, managing a small group of girls, just two or three, unlike the dozens I've got now, and I did as much hands-on work as they did. I think “hands-on” is exactly the right expression here.” She giggled, then went back to her story.
“I had already seen Mr Harris a few times by then; he wasn't my favourite client, but he was regular and generous and was usually happy just to watch while I masturbated for him; or sometimes he'd ask to see me with another girl and he'd get off from watching a bit of a lesbian show. He only ever watched, and didn't even want me or the other girl to suck him or stroke him; it usually ended with him jacking himself off into a pair of panties or some other item of lingerie.
'Well, one day after one of his regular sessions he was getting ready to leave when he asked if I would be prepared to do something a bit out of the ordinary: would I take a younger person's virginity? He would pay, of course, whatever I asked. I assumed he meant a young boy, as I had performed this ervice once already for a very shy young man. But in fact it turned out he meant Holly. He described her as a young girl of his acquaintance who he would very much like to see deflowered by a more experienced woman.
'“You mean you want to watch?” I said.
'“That's the idea,” he said. “I would like that very much.”
'“And this girl has never had full sex, with a man or a woman?”
'“No, she's completely untouched.”
'Naturally I wasn't going to turn him down, but it seemed a little, shall we say, peculiar. I was already reasonably experienced in lesbian sex, but not with anyone quite as young as Holly. As I say, it was early on in the days of the agency and I hadn't come across the range of sexual desire I now know exists out there. So we agreed a time and date. The only thing he specified was that I should wear a very formal skirt and jacket, “like a headmistress”, so that I could properly give this young girl her first sex lesson.
'When they arrived, Mr Harris was in very formal mode.
'“Good afternoon, Headmistress,” he said. “I'd like to introduce you to Holly. Say hello to Headmistress, Holly, there's a good girl.”
'“Good afternoon, Headmistress,” Holly said rather shyly, and she curtsied politely. She was dressed in a fairly standard school uniform comprising a short navy pleated skirt, knee-high white socks, black laced shoes and, to complete the picture, a navy blazer over a white shirt with a green tie. With her hair tied in two pigtails she looked really cute, and while I knew this was just a paying assignment, I felt my excitement levels growing; I realised I was actually looking forward to this.
'“Hello, Holly. I'm very pleased to meet you. Come and sit over here next to me. Perhaps, Mr Harris, you could take a seat over there in the corner. That's right. We'll try and forget you're there. Now then, Holly, what is it you wanted to see me about?”
'“I don't know how to explain it properly, Miss, but it has to do with certain feelings I've been having. I tried to talk to Mr Harris about it, and he suggested I explain it to you, since as a woman you'd be more likely to understand.”
'“Yes, I see. And what feelings might they be? There's no need to be embarrassed, you can tell me anything.”
'“Well, I've been getting this tingly feeling between my legs sometimes, usually when I go to bed at night. It's like an itch; and when I put my hand down there it makes me want to rub myself. And the more I do it the tinglier it feels. Then if I put my hand under my knickers, my fingers get all wet and I don't understand why – it's not that I want to go to the toilet or anything.”
'“Holly, all that is perfectly normal. You're a growing girl, your body is changing, you're turning into a woman. What you're experiencing is the beginning of womanhood. Your body is telling you that it can be used in a special way to give pleasure to yourself and, in time, to other people. Do you find yourself thinking about anything in particular when you rub yourself down there?”
'“Sometimes. I have the idea that an older woman is beside me, holding me, guiding my hand up and down, even putting my hand between her legs. And when I think of that it makes my mouth dry and my breathing gets faster until I get this shuddering feeling all over.”
'“What you are describing is something called an orgasm. It's when your body releases all that tension and you feel nothing but physical pleasure all over. Tell me, do you feel anything when I touch you like this?”
'At this point, I reached across and stroked her cheek, my finger moving across to her lips and touching them lightly. My other hand rested on her thigh and began stroking her leg softly, just reaching under her skirt. Her lips parted as I touched them and she gave a little whimper.
'“Yes, Miss,” she croaked. “I like that; it feels very nice.”
'I leaned in and kissed her forehead; then, still stroking her cheek and lips, I kissed her ear and her neck, my tongue darting out and flicking against her taut skin. As I kissed her like this, she threw her head back and let out a little moan. I kissed all down her neck to her throat, then up from her chin to her lips, till my mouth found hers and we joined in a slow, lingering caress. I nibbled on her lower lip and let my tongue meet hers, till we were French kissing and her breathing was becoming more and more laboured.
'“Do you like this, Holly?” I murmured. She simply nodded. I decided it was time to move things on a bit. I unbuttoned my blouse so she could see my breasts held firmly in my lacy red bra. Slowly drawing her head towards me I let her bury her face in my cleavage. She didn't need any instructions about what to do and was soon kissing them avidly. I shrugged off my blouse and unfastened the bra, holding up one breast and offering it to her sweet young mouth. Her lips closed round my nipple and she started sucking like a little baby.
'“That's very good, Holly. You can bite on my nipple if you like, that is another way of giving a woman pleasure. Let me do it to you, tell me if you like it.”
'I took off her blazer and hastily unbuttoned her shirt, leaving her tie on for the moment. Her breasts were small, barely anything at all, but very inviting. I leaned over and kissed her soft, soft skin and took each tiny nipple in my mouth in turn, not biting but pulling with my lips. Those sweet young nipples quickly became very hard and erects in my mouth. Her whimpers and other little panting sounds told me that she liked what I was doing.
'Working my way slowly down her body, I planted butterfly kisses on her soft tummy, savouring the sweet, warm smell of her young skin, the delicate touch of her downy hairs as I brushed my lips over her tiny navel, my tongue probing it as if it were another hole I could explore. She smelled of cream and honey and roses; good enough to eat, in fact. And how I now longed to eat her as she needed to be eaten; my own pussy was leaking as I played with her like this. I could feel juice dribbling down my inner thigh; I don't think I'd ever been so turned on by foreplay before and I was loving every minute of it.
'“Now, Holly, let me see how wet you are between your legs.” I knelt before her and raised her skirt up to her hips. Her white cotton panties were absolutely soaking over her young pussy, I only had to touch the wet patch with my finger and the cotton started sinking into her slit. I peeled her panties down and gazed in admiration at her beautiful, virgin cunt. The lips were swollen and glistening with her pussy juice; I touched her tentatively and my finger was already covered in her wetness.
'I had almost forgotten that Mr Harris was in the room, but a glance at the corner told me he was getting somewhat aroused. He had undone his trousers and was running a finger up and down his rock-hard cock. Mischievously, I tossed Holly's panties over to him and was delighted to see him wrap them round his cock and start rubbing himself with them.
'“You are so wet, Holly,” I said, turning back to the real object of my attention. “You see the way we're kissing and feeling and touching each other, you see how Mr Harris likes it. A lot of men like to see two women playing in this way, and you can see the effect it has.”
'Holly glanced over to see Mr Harris masturbating with her panties, but she didn't seem very interested or surprised; instead, she pulled my head towards her sopping pussy. I don't know how she knew what to do, but I wasn't going to object. I leaned in and at the first taste of that sweet young pussy my tongue exploded with delight. She was delectable, her virgin pussy juice like honey in my mouth. I clamped my mouth firmly over her cunt and licked and sucked as well as I knew how. Her hips were swaying and thrusting, pushing against my eager mouth, and suddenly I could feel her tense up as her body burst in one massive climax. Electric waves of orgasmic bliss pulsed through her tight young body and she gasped as she came.
'“Good girl,” I said. “That's what sex can be like with another woman. There are lots of other things we can do, but for now you've probably had enough.”
'I had clearly underestimated how eager she was, though, because far from having had enough she demanded more. First, she returned the compliment by unzipping my skirt and tongue-fucking me while holding my panties to one side. For Mr Harris watching from his corner, this is where he came the first time; as Holly had her face buried in my cunt, the back of her head framed by my black stockings, her bum in the air showing him her cunt and her ass-hole at the same time, he jerked himself off a little harder and shot a huge load of cum into Holly's panties, just as I came in my young lover's mouth.
'She continued licking me out as my orgasm gradually subsided, then pulled herself up so that we could kiss and taste each others' cum juices. I slowly pushed first one finger, then two inside her wet cunt as we kissed and my sweet little virgin, a virgin no longer, came again, squeezing hard on my fingers as she did so.
'To finish things off, Holly and I then scissored each other, our cunts grinding away as we held each others' legs. I have to say, for such a young girl she was a very enthusiastic lover, and so quick to learn. Mr Harris came a second time watching the two of us tribbing, but we were so wrapped up in each other that it barely registered. A third orgasm ripped through her as we rubbed pussies, her eyes wild with lust as they stared wickedly at me. Needless to say, Holly's panties were encrusted with cum by the time the two of them finally left.”
Rosie had finished her story and was now gently stroking my arms as she held me in her bed. I would really like to have stayed and engaged in some more love-making with her, but I had to go.
“Rosie, that is so hot. You sound as if you enjoyed that almost too much. Right now I wish I could stay, but I have to go now, I'm late already.”
“Yes, I understand. It was a wonderful experience, and made me realise for the first time in my new career that it's possible to take as much pleasure as you give – with the right person of course. Perhaps you've got a better idea of our Mr Harris and Holly now. Or maybe not; you be the judge of that. In any case, Mr Harris has asked for you to go over to his place on Saturday evening. He particularly asked for you, but he knows that it's not always possible to book a specific girl for a particular date. Would you be willing to do that, or shall I ask another girl to do it?”
“I think I could manage that,” I said.
“You're to go there at 10 o'clock and he's asked you to wear thigh-high leather boots and maybe some other leather accessories. He's not kinky, so far as I know, so it shouldn't be anything to worry about.”
“No, that's fine. I'll be there.”
“And one last thing. He says that if he's not there or if the house appears empty, you're just to let yourself in. He assures me it'll be open.”
“Sounds intriguing. I can hardly wait. I wonder what Mr Harris has in store for me now.”
“One way to find out. And be sure to tell me all about it.”
And with that, we got dressed, kissed and went our separate ways. I masturbated to Rosie's story of her encounter with Holly that day, and as Saturday approached I began to feel that familiar tingle of expectation that prefaced most of my engagements these days. I can't wait, and you, dear reader, will be the first to hear what happens.
Marisol
- 28.08.2021
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- Lesbian
