Sister

Latina

Literotica Guru
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Sep 13, 2000
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940
Jeff, I know you've been dating my little sister Alice for a couple of months now. I love my sister, but she is all wrong for you. Although we've never been really close or friends or anything, I've known you from school and around the neighborhood for a number of years, and I know you love a challenge. And I can see that my sister is no challenge for you. She is too young and immature to be challenging to you. I am older, more mature, more sophisticated, more experienced than Alice is or ever will be.

Alice is a nice enough person and all. Maybe a little too nice, a litte too eager to please, if you ask me. She told me about how in the restaurant on your first date, she was so eager to please you, to make a good first impression on you, to make you like her right away, that when nobody was looking, she slid down under the table, unzipped your slacks, and merrily proceeded to suck you off. She said you moaned and trembled and came so much that you obviously enjoyed it. And she loved licking your warm, thick, fresh spunk off of you. So ever since then, she has looked for ways to give you surprise blow-jobs. And therein lies the trouble. She has become too easy for you, she is no longer a challenge to you. Her last few blow-jobs, you've seemed very bored and distracted, and sometimes even had a hard time, well, a hard time actually getting hard! She told me that herself.

She told me this just isn't working out between the two of you, because you seem to be so bored with her. But she is just a timid, frightened little girl, too frightened to tell you face to face that it's over. She has been screening your calls, Jeff. Haven't you noticed she never seems to be home? She's home all right, she just waits to hear on the answering machine who's calling, and if it's your voice, she doesn't pick up, because she's too scared to talk to you. Haven't you noticed that she hasn't returned any of your last, oh I don't know, maybe 300 calls!

But she hasn't the courage to confront you, she's afraid you might tell her why you seem so bored with her. She hates confrontation, and would do anything, just anything, to avoid unpleasantness. I truly do love my sister, but let's face it, Alice has all the personality and charm and courage of a used, limp dish rag.

She actually asked ME to tell you it's over, rather than face you herself. I didn't want to do it at first, but she is my little sister, I love her and would do anything for her. So I finally, reluctantly agreed.

"Alice, Jeff's so cute and hot and sexy and all," I said. "So if you're really, truly sure you don't want him any more, if I do you this favor and tell him you're breaking-up with him, do you mind if I have a go at him?"

"Sure, whatever," Alice yawned. Then after a long pause to reflect on the situtation, she continued. "He is kinda cute, isn't he?" she smiled, giggling in that silly, immature way of hers. "But just because it's not working between Jeff and me, is no reason my big sis shouldn't have a crack at some happiness in her life. He is an amazing lover, I'd feel good about lettting you experience that for yourself. So yeah, sure, why not, go for it sis. If he agrees, I couldn't be happier for the two of you!"

Well, Jeff, I am not an easy girl like Alice is. You have to really work at what you get from me. But I know you are the type of man who enjoys a good challenge, and I promise you, if you are sweet and kind and gentle and loving and patient with me, the rewards will be more than worth it to you. I don't play mind games like Alice does. I am a straight shooter, I will always tell you what I am thinking and feeling, what I'm in the mood to do or not in the mood for at all. I won't go to bed with you on the first date, we have to really get to know each other first, you have to earn the sex by showing me love and trust and respect. But once you do, watch out, because I am a very fiery and passionate woman who honestly, truly enjoys sex. And I enjoy a good argument, too, I don't run from confrontation like Alice does. Besides, I know a little secret that Alice doesn't know: the makeup sex after a good fight is usually phenomenal!

So I really think you should say yes, you'll go out with me. I am much better for you than Alice ever was, we are a much better, more compatible fit.

"Besides, I am much cuter and prettier and sexier than Alice is," I smile, pulling down my shorts to flash you a very brief glimpse at my skimpy little panties, before pulling my shorts back up again. "My few years over Alice have given me a sophisticated sexiness that she completely lacks. Don't you agree?"

So what do you say, Jeff, do you want to date me? I promise to be a challenge like you need and want, but I also promise that once we really get to know each other, I'll really make it all worth your while in EVERY way.

I wait in eager, loving anticipation of your "yes" answer.

Suzanne
 
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Jeff

Dear Suzanne

Your nice letter was very timely. I was trying to talk to Alice for quite a while, to get to see her and tell her that it just wasnt working any more. Our first date was such a surprise when she went down on me, and I just loved it, but the chemistry just wore off and there wasn't anything left for us to depend on for our relationship.

When I picked her up that night I saw you again and the whole time she was doing me under the table, I was thinking of you and fantacizing about it being you down there. She is really cute and nice, but your loveliness far outshines her and I want to get to know you better - a lot better.

Once I had dated her I couldnt very well hit on you as I had to stay loyal to her, especially considering the way she was doing me every time

When can we meet and talk personally? I am free this Friday night, but it might hurt Alce if I picked you up at your home. Can you meet me at the mall in front of the fountain at 8?

I look foreward to hearing back from you, hopefully with a nice big YES
 
My heart races as I read your note and I realize that at last I get to go out on a date with the hunky stud of my dreams. Meet you at the mall? You bet I will! Alice told me all about how smart, funny, fun, and loving you are, so I feel like I hit the jackpot getting to go out with you. And trust me, you are definitely going to be getting the better sister by dating me, now that you and Alice are splitsville.

I'm so eager to date you that I actually get to the mall a half hour early, giving me time to look around a little before I meet you at the fountain. You stroll up precisely at 8:00 as promised, and my eyes cannot believe how hot you look. I remember what Alice said about what an amazing lover you are, and I can hardly wait to experience first-hand everything that Alice has for so long boasted to me about you. But that won't happen tonight. I'm not the type of girl to jump into bed with a man on our first date, not even with you. Besides, you are a man who relishes a challenge, and what sort of challenge would that be if I throw myself at you on our first date, the way Alice did? No, it usually takes many, many dates, getting to know each other for a very long time, before I feel comfortable about having sex with a guy. But in your case, you look so hot, and Alice has boasted so much about the sex with you, that I just might make an exception, maybe after only 2 or 3 dates.

"So," you ask, "what do you want to do tonight?"

"I don't know," I shrug, smiling. "What do YOU want to do?"

"I don't know," you reply, not being very helpful.

"Well," I offer, "while I was waiting for you, I noticed that Victoria's Secret here in the mall is having their $9.99 bra sale."

"Why?" you grin, leering at me. "Do your big, firm, beautiful boobies need a new bra?"

"I forgot to wear a bra at all tonight," I smile, lifting my T-shirt and flashing you a view of my big, full, round breasts. "And it's damned cold here in the mall, which as you can plainly see, is making my nipples so hard that they ache. Well, OK, I'll admit that maybe the sight of you has something to do with my nipples getting so big and hard, too. Anyway, I'd be much more comfortable on the rest of our date if I can keep them all nice and warm in a nice new bra. Besides," I grin, "I'll bet you'd like it if I model a new bra for you, wouldn't you? So let's go to Victoria's Secret now, and then I'll let you pick our next activity for tonight's date."
 
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Jeff

We walked down the mall aisle to Victoria's Secret, and entered. I was fascinated with the lovrly lingerie on the mannequins, especally the little skimpy thongs. I had to wonder since she wasnt wearing a bra, what kind of panties (if any) she was wearing.

I wandered around as she found the bras, and started to pick out what she was interested n I looked over her shoulder and noted the size she selected, and thought about how nice her breasts would feel in my hands or mouth, if we ever got to that.

The very attractive female clerk asked her if she needed any help, and when she saw me ogling both of them she blushed prettily and politely receded from vieew, as I was led to the fitting room with several possibilites in her hand.

What a way to start a date and a relationship!
 
Did he guess, I wonder, that I am not only braless, but pantiless as well? It doesn't matter. I picked out several sexy bra-and-panty sets, and some more conservative ones as well. I decide to model them all for you. But no point getting you too excited too early on. I start by modeling a more conservative pair of panties. I decide to let you see me in only the panties first, and then add the matching bra later.

I emerge backwards from the dressing-room, my back toward you, in only panties and nothing else.

"I decided to buy panties to match the bras. I thought I'd show you the panties first, before I show you teh matching bras. So I'll start with this one. Do you like it? How do I look?"
 
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"Oh, I'm not being fair to you," I giggle. "How can you judge how I look in these new panties, whether I should buy them and wear them, if you only see them from the back?"

I spin around to show you the tiny triangular front of my panties. But since I am still braless, your gaze somehow mysteriously seems to be fixed much, much higher than on my panmties now.
 
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Jeff

She went in alone, quashing my hopes that she would take me in with her. The salesclerk watched us with scrutiny, and headed over to supervise and help if needed, and I was sure she would say something about the whole armload of stuff Suzanne had carried in.

We were left outside with the door closed. The clerk smiled at me and slipped me her card, with her home phone number pencilled in on the back and the words "call me"

Suzanne appeared walking out backwards, with a tightfitting and almost transparent pair of panties on, and nothing else. Fortunately we were alone in the store, as she modeled them for us and then suddenly porouetted around and showed me the front, wearing nothing up above. She was totally nude except for the panties which hid nothing. Her very black bush showed right through, except there was very little of it. She had trimmed her hair to just a thin strip above her slit, which looked most delectable. I wanted to drop to my knees and start kissing there, but was awestruck by the lovely pair of tits just begging to be kissed and licked.

In my note i had told her how she had really dimmed the lights around her sister Alice, and now I knew for sure. She was about a 29 on a scale of 1 to 10.

The salesgirl also looked at her, and followed her back into the changing room to put on another garment to show me.
 
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I had headed back into the changing-room to try on another outfit, but then I realized that you had not told me what you thought of the pair of panties that I just modeled for you. Should I buy them, or should I buy a different outfit? So I re-emerge from the dressing room, still wearing this first pair of panties.

"So, Jeff, you didn't tell me. What do you think of these panties?"

"I think they look hot on you," the sales girl offers.

"No, what looks hot is my Jeff here. And I just decided, these panties aren't nearly cute enough and sexy enough to wear for my first date with my hot new hunk. Not NEARLY good enough for my Jeff! So I'll have to take them off and try on something else."

Neither you nor I nor the sales girl had noticed the leering old man before, lurking in a corner of the store, until he calls out now "Yeah, baby, strip off those panties!"

I am suddenly feeling very uncomfortable, shy, and inhibited. I silently clasp your hand in mine, and I pull you with me toward the dressing-room. You start to ask me what I am doing, but I put my finger up to your lips. "Shh, Jeff, don't say a word. Just come with me into the dressing room."

In the dressing room, I feel much more comfotable and relaxed, away from the prying eyes of the sales girl and the dirty old man. I am not the least bit inhibited or self-conscious now about stripping off my panties in front of you, preparing to model another outfit for you. But it occurs to me that I OUGHT to be self-conscious now, about standing completely stark naked before you now on our first date. I realize why I am not self-conscious: because I have know you as a classmate and a neighbor for years! Besides, I fel I know you quite intimately from all the details my sister Alice has dished to me about you over the past 4 months that you dated her.

Besides, you've seen my sister Alice naked about half a bazillion times. And it is not idle boasting, but true self-confidence, when I say that I know for a fact that I have a way cuter and sexier body to show-off to you than my little sister Alice does.

Besides, I know I don't have to worry about being naked in front of you. I know you to be a true gentleman who will honor my strict "no sex on the first date" policy. I know that you will enjoy the show I am putting on for you, that you will look but not touch.

And so I linger naked for a few moments more. My intention is to try on a very sexy, sheer and lacy black lace panty for you next, with a matching black lace bra. But not yet, not quite yet, as I enjoy my nakedness a moment longer, and as I let you savor the moment for a little longer as well.
 
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Jeff

It was Friday night and I'd just been paid at my workplace. I had a pocketful of money and nothing to spend it on except sweet Suzanne.

I sat on the little bench when she talked, and as she stood in front of me naked, less that two feet away, with my face staring at her sexy pussy, I just blurted out that I thought the panties were perfect, as anything would be on her. I told her to buy everything she wanted and flashed the wad of bills from my cashed check

Secretly, however, I hoped she would never wear panties when she was with me. I preferred to think of her just the way I saw her, wearing a smile on her face, and nothing else, and defying her vow of no sex on first date, as she stepped toward me.
 
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Jeff flashes a wad of money, and I try not to act impressed, but I am a little bit. But I know he doesn't make much money, and he needs that wad of cash to pay his bills. So as sweet as his gesture is, I cannot in all good conscience accept his offer to buy me all the bras and panties I want.

Besides, I only need one bra and panty set at the moment, to wear on tonight's date, and I have the money to buy that. Still, I decide to let him buy the one outfit for me, so as not to crush his proud male ego that so wants to buy things for me. But I accept his offer only on the clear understanding that his buying me a present does not in any way obligate me to him sexually.

Still naked, I turn my backside to him, and I stoop down to pick up the next outfit that I placed on the dressing-room bench. "I need an outfit that really complements my ass. That first pair of panties just didn't do it," I say, spreading my legs apart a little so you can see just a hint of my pussy from behind.

You gulp at the sight of my bare ass and the hint of my bare pussy. "Any outfit would compliment that!" you eagerly declare.

"How sweet," I say, kissing you lightly on the lips as I slip into a black lace bra and matching panties I laid out earlier, to model for you. "How do THESE look? I think they're MUCH better than the first outfit I moldeled for you. Don't you agree?"
 
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Jeff

When she bent ove with her back to me, thee were thse perfect ass globes fraing her bare pussy and asshole. I just couldnt resist, I leaned over and kissed the cheek of her ass.

She looked at me with a start then smiled as she climbed into the next outfit for me to see. I had aleady seen everything I ever wanted - Suzanne!, but the panties really looked good on her, as anything would, but these were especially stunning.

To prove it to her,I pulled her to me and kissed her right over her pussy, and then she pushed me away by kissing my lips, but she didnt stay long enough for me to slip my tongue into her mouth.

Then she got dressed and we walked out of the dressing room and returned the rest of the items to the shelves, and went to the clerk to pay for the outfit we had selected. It was now late and te store was closed, and she had locked the door and kicked the voyeur out.

She sweetly said "come back and see me any time", and seemed upset we were leaving. If we hadnt locked the door of the dressing room when we went in together I was sure she would have come in too, and I did hear her try the door. I didnt know if Suzanne was into playing with girls, but theidea appealed to me ad I had her card, and maybe some other time it might work out
 
I feel so good, so sexy and self-confident now, in my new black lace bra and panties, that my new boyfriend Jeff has just bought me. That new self-confidence reflects in the spring in my step.

"So, what do you want to do now?" I burble cheerfully. "it's your turn to pick an activity."

"Well," you say, "Frederick's of Hollywood stays open later, and they have an extensive men's section. It's so late that we'll probably be their only customers in the store. Besides, you just modeled some very sexy outfits for me, so it is only fair that I model some sexy male outfits for you now. Would you like that?"

I joyously nod my assent, and I try to picture you in the skimpiest of underwear, as we quickly walk hand-in-hand across the mall to Frederick's.

You grab several outfits, without letting me see what any of them are, and you disappear into the dressing room. You emerge in the first outfit, grey cotton. It looks nice enough on you, and you definitely have the hot male physique to wear this stuff, but it is a little plain looking, being solid grey color.

I think you sense how disappointed I am in the drab color of your first choice, as you quickly disappear back into the dressing-room, without actually asking me my opinion first.
 
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Your second choice isn't much better, maybe even worse: it's brown and shapeless!

Come on, Jeff, how about a little bit of color?
 
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Your third choice is much better: shimmering black, much more revealing of your deliciously hunky male body. But I still hope to see you in something more exotic and colorful than what you've shown me so far.
 
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Jeff

All three of those skimpy thongs obviously just didnt do it for Suzanne, so i led her into the changing room with me, and dropped the black garment on the floor. By now I was hard and horny as hell. There was only one thing I wanted to wear on my cock - her mouth or pussy, and with her sitting on the little bench, I offerred myself to her and let her choose.

I knew what was under her little skirt, and i wanted it and she knew it as she smiled up at me
 
Jeff pulls me into the dressing room with him, so he can show me a few of the racier outfits he picked out. He is too shy to show me them in front of the sales clerk. His shyness is cute and refreshing, and attracts me to him all the more.

Yet he seems not at all shy about changing before me. As his hard cock springs free from his thong, I hungrily lick my lips.

"Now Jeff," I warn. "You promised to respect my 'no sex on the first date' rule. You're not playing fair. Your beautiful hard-on is making it hard for me to stick to my rule."
 
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"Oh, sorry," Jeff smiles as he slips into a more revelaing and more colorful thong now, a faux leopard pattern.

"Mmm, better than the others," I smile. "But no. Not quite right just yet."
 
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Jeff slips into a bright blue-and-gold number.

"Mmmm, much better!" I coo. "Much, much better!" I don't know which is turning me on more now, the outfits or what Jeff is showing me between costuime changes. My younger sister Alice clearly did not exxagerate about what a hunk Jeff is. If anything, she understated the facts.
 
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Jeff can see the effect he's having on me, and he remembers that he promised to be good. So before another costume change, he asks me to leave the dressing room. He doesn't want me to see him change into the next outfit, he wants to step out of the dressing room and surprise me with it.

I pout a little. I don't really want to leave. But when Jeff emerges in nothing but a tiny black pouch, I know he was right to surprise me with it in this way. "Now, THAT'S more like it!" I cheer and catcall. "Buy that one!"

"But I have one more to show you, that I think you will really, REALLY like," Jeff grins, pulling me back into the dressing room once more.
 
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Jeff's final outfit is bright red, not as revealing as that black pouch he just modeled. But it hitches at the side, and as he starts to hitch it close, I whisper "Don't you dare." I grab the side and unhitch it back open again, practically drooling at the sight of his exposed hard cock as the red bikini underwear drops away from him and falls softly to the dressing room floor.
 
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I know what I must do now. Jeff is standing before me, completely naked and vulnerable and inviting, and I know that he wants me to be naked too now. So I slowly, seductively strip off first my street clothes, and then the pretty new black lace bra and panty set that Jeff just bought me. And I sit back on the soft leather dressing-room chair, my legs slightly apart, silently inviting him into my open and welcoming arms, into my heart, and into my steaming-wet pussy.

"I changed my mind about that no sex on the first date rule after all, Jeff," I smile. "I can't help it. You look so amazingly hot, both in and out of your skimpy underwear! I'm only human, I can't hold out one moment longer."
 
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Jeff

As she sat, I fell to my knees and worshipped her. When m head bowed, it found itself right between her legs with my lips on hers, and my tongue probing and searching her inner folds. She met each tongue thrust with one of her hips, and quicky being so turned on with all the playtime, she shreiked and lurched and emitted a flood into my face.

I was sure it could be heard throughout the store but I didnt care.

As she sat back and rested I continued lavijg her and inhaling and tasting her. Soon she started to arise, and pushed me down in the chair. She climbed on my lap facing me, with her legs astride mine, and sank herself down on me.

Fully immersed, we kissed and kissed and our tongues played too, sharing her tastes. We both knew we had found heaven together, and this was the first of many
 
As I lay back in the dressing-room chair, I hold my pussy lips wide open for you, allowing your talented, swirling tongue unobstructed access to my clit, my G-spot, and anywhere and everywhere else that you care to kiss and lick and suck and nibble now.

Alice told me so many times what a wonderful, gentle, slow and patient lover you are, and now at last I am learning for myself, first-hand, just how skilled, kind, and considerate a lover you truly are.

Finally, we change places, you in the chair and me standing before you. I climb up on your lap, facing you, and I slowly slip myself down over you. Mere words cannot describe how good this feels now, and how quickly and how deeply I am falling completely in love with you.

I still want to be a challenge to you, so you will never get bored with me. But I will have to challenge you in ways other than sex. Just like Alice, I find myself helpless to resist your magical sexual powers over me, to be a challenge to you in this aspect of our budding relationship.

But you seem to take a challenge upon yourself now: to pleasure me in new and exciting and unexpected ways, so I will never fall out of your sweet, loving power over me.
 
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Jeff

Just as she reached her peak, she let out a loud shreik. Suddenly the door opened, and there stood the manager who had apparently opened the lock with his key.

Caught in the act, and both of us nude and dripping with cum, he started to laugh and said he thought that was what we were doing, and please get up and let's clean up the room.

We did so, not bothering to dress, but being in and out the door while we wiped up a puddle on the leather chair. We had a giggle or two as he told us of similar events in the past in his dressing room.

I could tell he was getting turned on, and all of a sudden out of the corner of my eye, was a lady peering in at us through the window ar the front of the store. It was Elyse, the clerk at Victoria's Secret where we had been earlier and who had given us her card and home phone number.

She rapped on the window, and Tom, the Manager went to let her in his closed store, and the four of us faced off with Suzanne and me still naked.

Elyse kissed Tom hello, and after she led me into the second dressing room similar to the one we had used, she told me that she and Tom were friends and occasional lovers. As she got undressed, we heard sounds from the other room indicating that Tom and Suzanne were getting it on too.

What fun! What a night!
 
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At first I feel selfish about feeling lust for the handsome Frederick's store manager, Tom. After all, I'm supposed to be building a relationship with Jeff. But Jeff reassures me that he wants me to do this, he loves me enough to want me to have fun, and he trusts me enough to know that sex with another man will not lessen my very strong feelings for Jeff.

And when I hear Jeff in the next dressing room, starting to enjoy Elyse, the cute sales girl who followed us from Victoria's Secret, I know that this is Jeff's way to give me permission to do all the deliciously naughty things I am picturing myself doing with Tom, the Fredrick's of Hollywood store manager. And I love and trust Jeff enough to know that his sex with Elyse is just that, just sex, it doesn't mean anything really and doesn't at all affect how we feel about each other. After all, we are four mature adults here, and jealousy doesn't prove how much you love someone, it only proves how insecure you are. Jeff and I are secure enough in our feelings for each other to enjoy this unexpected chance at fun that life has given us with these two retailers, without either of us attaching anything weighty and emotional to this chance encounter.

Although I am naked, I decide to slip back into my newly-purchased black lace bra and panties before we start. I loosen Tom's polka-dotted yellow power tie, and I slip it over his head without unknotting it first. Seductively, playfully, I slip his tie down into the front of my black lace panties, squealing and squirming at the sensuous feel of the soft silk of his tie gliding over my soft, wet pussy lips.

Tom slips out of his navy-blue suit jacket and neatly folds it over the back of the dressing-room chair. I slowly unbutton Tom's crisp white shirt, but I leave it on him as I lean in and kiss his hairy, muscular chest. He wraps the shirt around my head, as if trying to hide what we are doing from any prying eyes that might accidentally enter the dressing-room. "How sweet and charming," I think. "He's so shy!" After all, the store is closed, only Jeff and Elyse are still in the store with us, and judging by the sounds from the next dressing room, they are far too busy with each other to bother about us.

I kiss my way up from Tom's chest, past his neck, to kiss him full on the mouth, our lips locked tightly against each other, our mouths open just enough for our tingues to lightly, playfully touch each other.

Without breaking our kiss, Tom delicately pries my hand and his necktie out of my panties. He places his open palm flat against the front of my panties, and he slowly glides one long, extended finger up and down the front of my panties.

"Ohhhh!" I moan. My moans are as much for the benefit of my new boyfriend Jeff in the next dressing room, as they are to tell Tom what he is doing so right to me, with me now. I secretly hope that Jeff and Elyse will be as verbal, so I can follow exactly what they are doing to, doing with, each other now.
 
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