Jenny Becomes A Woman free porn video

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It was 1998 I turned 16 and my world was opening up for me. I felt excited about the future and in love with life. I was always known to be cute but this year I was really changing...my breast were getting bigger (36B), my hips seemed curvier, my legs longer (I was 5”4”), my body becoming firmer since I started cheerleading and running after school every day and boys were lining up to ask me out on a date even the older boys were starting to notice me. I felt good. Alive!

Every day I would walk home after school. There was this one house I enjoyed walking past because there was a really great looking man who lived there. O I knew he was too old but boy was he so cute! And nice as well. He usually was outside working on his lawn or washing his car when I walked by and we would always say hi. It just thrilled me he noticed me! Occasionally I would ask him a question or he would ask me how I was doing in school. I secretly hoped he would notice how sexy I was becoming. Every now and then I could have sworn I saw him look at me up and down with a twinkle in his eyes. I felt so incredible afterwards. God, I wish I were older! It’s crazy to think that a man like that would really ever notice me or even consider me sexy but I liked my fantasy. O don’t misunderstand me, at this point I was just a silly 16 who knew nothing about sex. I just had feelings I didn’t know how to explain but I didn’t go any further than that. I was an innocent and naïve not at all aware what was on the mind of a man his age.

One day when I was walking past his house, he was outside washing his car and called me over. So I walked up his drive thrilled he called out to me. He had such a wonderful deep voice. I loved listening to him talk. He asked , “Hey princess, how ya doing? I was wondering if you could do a really big favor for me?” “Sure”, I responded rather eagerly. “Well, you see I am going away for the weekend and have no one to feed my cat while I’m gone. I was wondering if you would be interested in doing that for me?” “Sure. When are you leaving?” I asked. “Friday morning. So, I thought maybe after school on Thursday you could come by and I’ll show you where her food is and give you the key to the house.” “Thursday? Well, I have cheerleading practice after school so it will be a little later than usual. Is that ok?” “Yeah”, he said, “no problem. I’ll be home. Thanks. I really appreciate it. You’re a sweetheart.” “No problem, Mr. Saunders. I’m happy to do it for you.” “Please, Jennifer, call me Rick. You make me sound so much older than you. Besides, we’re friends right?” “Yeah, sure….Rick….we are. Well, I better get going. I’ll see you tomorrow!” “Ok, Jen, see you then.”
Awesome! I get to see inside his house! And he asked me….ME! O my god, I can’t believe it!” I walked home that day feeling on top of the world. I couldn’t wait for Thursday to get here!

Sure enough, Thursday arrived and cheerleading practice seemed to drag on but finally it was done and I was walking home to Rick’s house. As I walked toward it I noticed another car in the driveway. He must have a friend over, I thought. I walked up to the door and rang his doorbell. A few seconds later (it seemed like eons), Rick opened the door. “Hi, sweetheart! How are you? You look fantastic! (I was still in my cheerleading uniform)” I beamed, “Thank you. Hope I’m not intruding. I see you have a friend over.” “No. Not at all. In fact I’d love for him to meet you. Come over into the living room.” As we walked into the living room, Rick put his hand on my back and guided me in. There before me was another stunning looking man. I felt awkward and nervous as though all of a sudden all my flaws had a spotlight beaming on them. Rick introduced us and we shook hands. He had nice hands and they were warm. He looked at me like he was very pleased and was enjoying a good joke. I felt warm all over.

We stood there close together the three of us while we asked each other questions about ourselves. All the while, Rick kept his hand on the small of my back. It made me nervous and warm all at the same time. Occasionally, Ed’s eyes would dart to my breast which I am sure was heaving because I was having difficulty breathing evenly with these two men so close to me and all alone in Rick’s house. “What?” I was brought back from my wandering thoughts by Ed’s question. “I said. A girl like you must have a lot of boyfriends after her” “Who me? Ah, well, I have a few who ask me out.” “You are beautiful, don’t you know that?” he asked. “Who me? Well, I think I’m cute but beautiful is not a word I would use to describe myself.” Ed was insistent. You are beautiful and you’re body is gorgeous!” He brushed the back of his hand against the side of my breast. I instantly stepped back but Rick’s hand was there and he pushed me forward so that I couldn’t step away! Ed’s hand kept brushing against my breast now he was roaming kind of all over still using just the back of his hand. I felt trapped between these two men’s hands. I was intrigued and scared all at the same time. My fear must have shown on my face because Ed spoke very soothingly and told me not to be afraid that woman who are as beautiful as me with a body like mine really know how to please men. I thought, wow I’m really wanted! And yet I was scared I didn’t know what was going to happen to me. I wanted him to keep touching me and I wanted him to stop.

I felt Rick softly hold my arms at my side while Ed mesmerized me with his stroking of my breast. Every now and then he would rub his thumb across my nipple or squeeze them gently. Ed’s eyes were heavy looking and seemed glued to my breast. He kept saying how beautiful I was and asking me if I like what he was doing? I don’t even know if I answered. I just let him touch me. His stroking got rougher and he squeezed me harder. He also began to pinch my nipples through my uniform using both his hands pulling at them as though he wanted to pull them out right through my top. I was heaving and leaning back. I noticed that Rick had pulled my arms back and forced my hands to cup his crotch. One hand holding my hands there and the other holding my wrists. I was beginning to panic and I tried to pull away and wiggle away, but Rick just firmly held me there whispering how good I was making him feel and how good I was going to feel. I told them I don’t think we should be doing this and that Im scared could they stop and let me go. “No baby. You are going to love this. I promise. Just let us show you how to please us. It’ll make you feel like a goddess!” Ed adds in his sultry deep voice, “Yeah, that’s right, baby, c’mon let us make u feel real good. Your body is so awesome. So beautiful, baby.” C’mon lets sit down on the sofa over here. Take a little break. Ok?”

So, Rick lets go of one of my arms and Ed takes the other guiding me over to the sofa as though I needed help walking. We sit on the edge and I take a much needed deep breath. “Whew. That’s better. I’m nervous, guys. I’ve never had a boy, let alone a man, touch me like you are touching me.” Rick and Ed place their hands on each of my bare thighs and told me how great I am doing and that there is nothing to be afraid of. They won’t hurt me. They were sliding their hands all over my thighs and I was getting those nervous butterflies in my stomach again.

“You like that, don’t u baby?” Rick asks me. I look into his eyes and told him I liked him touching me. He smiled his big beautiful smile and said, “then would you lift your shirt up for us? Let’s see those beautiful breasts of yours.” “No, Rick, I can’t. It’s not right.” “Aw, c’mon sweetheart. Since I first saw you I have been wondering what they look like. I imagined what they felt like under my hand. I’ve wanted to touch you for so long. You are so beautiful baby.” He began to reach for my top and pulling it up. “No, Rick. Ed. Stop please. I don’t want to continue. Just stop please. Yes it feels good but it’s not right. I’ve got to go. Let me go.” I tried to stand up but Ed held my arm and would not let me leave. Rick reached again for my top and began to pull it up. I squirmed and wriggled trying to stand up and keep my shirt from being pulled up, but they slipped it up over my breasts and pulled my breasts out of my bra. I felt humiliated. “Please don’t. I’m asking you please stop.” But they ignored me and they each fondled by breasts telling me what beautiful tits I had. Then they lowered their faces and started sucking them and squeezing them and kissing my mouth and my neck….O my God…. Please stop. Please don’t do this. Im scared.” I kept wriggling away as best I could but they held me firmly. It was then that my body began to betray me. There I was with a man on each breast sucking . Feelings started surfacing I never knew I had. My vagina was getting this weird pulsing feeling and horrors of horrors I wandered if one of them would touch me there! No sooner had I thought it I felt Ed’s hand slip up my skirt and touch me there. O god….I opened my legs a little wider! Ed slipped his fingers under my panties and began rubbing me all over down there. He whispered in my ear how fucking wet I was and …”See didn’t I tell you you were going to love this?” “That’s it my dear spread those legs wider. Because in a moment I am going to kneel in front of you and take those panties off and lick that beautiful tight wet pussy of yours.” O god that sounded delicious. I think I was whimpering by now. “Please. Please don’t stop. I don’t ….under….stand…what…..I…am…feeling….but o…..it ….feeelssss….sssooooo…….goood…..Rick? Rick? O god your mouth on my tits….don’t stop…..pleaseeeee….

Ed stood up and knelt before me and pulled my panties off. He spread my legs wider because believe it or not now that the moment was here I was scared and I put up a little resistence. He spread them apart and his head lowered to my vagina. Omg! So good. He was licking me there! I can’t believe it anyone would want to do that but he seemed to really be enjoying himself. And I was glad he was. O it felt so good that consistent licking up and up again just like he was licking ice cream off a cone.

Rick all of a sudden stood up and unsnapped his jeans and pulled something out of them….omg it was his thing~ and it was huge! There it was sticking out like a rod pointing straight at my face. “Suck me, darling. C’mon. It’ll make me feel so bloody good.” I shook my head. “No, Rick, I’ve never done that.” Rick put one hand around his thing and the other behind my head and forced it into my mouth. Then he pulled it out a little and shoved it back in. He did this back and forth motion forcing the back of my head so I had to suck him. I had to breathe out of my nose because he wasn’t giving me any chance to take a breath. While he was forcing me back and forth he said “Yeah, baby, suck that cock. Ohhh it feels so good. You are so good, Jen. God you make me feel so fucking good. That’s it baby suck faster. Faster. Suck my cock, bitch!” With what Ed was doing to me down there and sucking Rick’s cock I went crazy. I felt something building but didn’t know what was going to happen. I all of a sudden felt like I was going to pee. They both told me it was okay to let it happen. “Let it happen baby! Let it go!” I had no choice it was so intense I screamed as best as I could with Rick’s cock still in my mouth and then liquid squirted out of me. I was so embarrassed. Ed was lapping it all up though. I was astonished. I was told later that I experienced my first climax and that it wasn’t pee but cum. Wow that felt awesome!

I thought it was all done but that wasn’t all they had in mind. Ed stood up and took his pants and underwear off. He sat back down against the coffee table and told me to suck his dick just like I did with Rick. I crawled over to him and began to suck his cock like I did to Rick. Then I felt Rick grab my butt and feel around my vagina and the next thing I know he was pressing his cock into my vagina hole. “Ouch, that hurts a little Rick! What are u doing?” “it’s okay baby it might hurt for a moment but It’ll be quick. Just let me slide in, darling. It’ll be over quick. There. One… Two …..Three” and on three he thrust himself into me until he couldn’t go any further. Oww…I whimpered. I wanted to say tell him to stop and take it out, but Ed had a hold on my head and wouldn't let go. I felt Rick caress my back and butt and say “It’s okay baby. It’ll be ok. Just be still for a moment. Keep sucking Ed. Like I had a choice! Ed reached up with one of his hands and fondled my hanging tits pinching my nipples which drove me crazy. Meanwhile, Rick is caressing my back and butt , moving back and forth inside me and started to fondling my vagina. It was actually starting to feeling good. Ed kept grabbing and pinching my tits and Rick’s movement became stronger thrusting himself into me faster and faster. I became frantic for something again and I couldn’t suck Ed’s cock hard enough or fast enough. Ed grabbed my head with both hands now and forced me to go faster and faster . Rick was rubbing me fast and hard now and thrusting harder in me and yelling he was cumming. Just then I felt I was cumming with him and wanted to scream, but couldn’t. “Damn!” Rick yelled and with that one final thrust I felt hot deep liquid inside of me. I looked up at Ed and he looked in pain but kept thrusting himself into my mouth. “Ok baby here it comes. You’re going to get a nice big drink!!” And with those words out came a thick liquid from Ed’s cock. Right into my mouth! I gagged and he held my mouth over his cock and yelled for me to swallow it. I had no choice. I swallowed. Then Ed slowly pulled himself out of my mouth. Whoa! I sat back on my knees wiped the sticky liquid from my lips and realized I just lost my virginity and I just graduated into womanhood.

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Jenny

Jenny's first time. this story is about a 24yo crossdresser who calls himself Jenny and his adventures.jenny is 5'11, 60kgs ,complexion-very fair(which made his job of turning into a girl much easier).he had nice long hair which looked good on him,with his slim and hairless body and long legs. he face was very girlish and didnt really need much make-up when he dressed up, but he still loved applying a lil of sumthing, just to make it more sexy.Jenny had 2 sisters and many cousin sisters, this...

1 year ago
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Jenny Is a Friend of Mine

“Hey Danny, how you doing? That was a fucking top night last night. Here have a drink on me” “Hi Jenny, thanks, I drank way too much last night, could I just have a glass of milk please.” “No worries,” Jenny grabbed a pint of milk from the fridge, “still on me though...” “Thanks, mmm that’s nice and cold.” “So, what you going to do about the Chloe & Lorraine situation?” We were sat on a sofa in the pub, I was the only customer late on Sunday afternoon, Jenny was the only member of...

2 years ago
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Jennys Den of Iniquity

Over the years I have worked for a number of bosses, but only one female, her name was Jenny.Jenny was a confident woman with an air of sexuality, and a nice pair of tits to go with it.When Jenny got horny, Jenny got fucked and fortunately for me, I was in the right place at the right time.Jenny owned the company, so any job that she asked me to do, I was happy to do it.One day, she told me that she had an issue with one of her electrical items at home, and would I be able to see if I could fix...

3 years ago
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Jenny Our Vivacious Pet Sitter

Our family decided to go on a short vacation to New Mexico. As a far as vacations go, it was a long awaited and much anticipated vacation. We are a cost conscious family, so I decided to look on line for a pet sitter for our very friendly great Pyrenees. I found an add on social media that read: “TEACHER NEEDING SOME SUMMER TIME FUN AND PAY- WILLING TO PET SET!” I texted the number and then looked up the person on social media. I was immediately struck by the profile photos of a strikingly...

Cheating
2 years ago
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Jenny comes home finally first fucks 5

Time to take juicy Jenny finally for her very first timeSince school sent her home for private punishment for her public pussy showing there,my dear dirty doddie had developed a fondness for serious spanking of private parts.Coming constantly without my permission, she postponed effectively her first fuck.Still she longs very much for it, as she is so in love with her mentor and teacher.Jenny badly needs to go to the bathroom, but I do not allow her to relief herself.To make sure she will be...

1 year ago
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Jenny my sister friend stays the night at our house

Note : This story is completely fictional!  my sister "jill" had a friend "jenny" come home with us after school to stay the night at our house. jenny was nineteen years old and so was my sister. i was one year young then the both of them. i got to the house first before my sister and jenny. i have never meet jenny and did not know if she was hot or not. so i run upstairs and jump in the shower. i get all dressed up like i was going out on a date or something. just as i was walking back down...

Incest
3 years ago
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Jenny Pt 2 Jennys Desk Job

Hello, my pet. There's been a change of plans. I had to go to the office to meet with a client—and he's made a lot of last-minute changes, which means that I have to stay here for awhile. So I want you to come down here to my office so I can amuse myself with you while I work. Tell the receptionist you're my new assistant—she'll tell you where to find me. Dress appropriately. See you soon... Darn, Jenny thought. She'd been looking forward to having Him come over. She'd put on her...

4 years ago
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Jenny Ch 04

This is a re-posting of an earlier story. I have re-edited it to improve the punctuation, grammar and, I hope, the readability. Tom sat on the edge of the stateroom bed, slowly undressing as he waited for Jenny to return from the head. He was unusually tense for a reason. He had made up his mind, and this was his moment of truth. It wasn’t that he had any doubts, but he was entering uncharted waters, and he wasn’t quite as sure of himself as he’d like to be. Jenny opened the door and quietly...

4 years ago
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Jenny 1

Jenny was quite excited; her friend Susan was back from her short holiday and they were meeting for lunch and a catch up at Jenny’s well-appointed house. These two had been very close friends for many years and the two of them enjoyed time together with their husbands Derek and Simon. They also enjoyed time together on their own in a very special way. These two very attractive ladies, pillars of the community and both on various committees for both the church and other local institutions. How...

1 year ago
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Jenny shows her gratitude

Few years back my niece Jenny stayed with us for a month as she was going through a difficult divorce. Her then husband was constantly creating problems and Jenny wanted to stay with us instead of her mother. Jenny is my oldest brother's daughter and I am about 20 years older than her. After three weeks, it was quite clear my wife Linda could not stand Jenny in the house anymore. Finally, I was able to convince my wife to go attend a wedding in her side of the family and I promised her...

Incest
2 years ago
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Jenny and I3

I had plenty of time to rest and eat some lunch before Jenny showed up from work. She was a little bit tired, so we sat on the sofa in the family room to talk for a few minutes while she rested. For no reason other than just making conversation, I told her what had happened at Mrs. Jackson's house that morning. With practically anybody else, I would have been better off keeping my mouth shut about Mrs. Jackson and the fucking episode.However, Jenny and I had always shared our secrets. I guess I...

4 years ago
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Jenny Ch 02

This story is a re-post of one of my original stories in the Quartet series. I have re-edited it to improve punctuation, grammar and, I hope, readability. * Jenny awoke at her usual hour of seven that Sunday morning. As she pulled off the covers and swung her leg over this side of the bed, she immediately became aware of soreness in her vaginal cavity. It wasn’t acute, but it was noticeable. Her mind went back to the evening before, and her trepidation about Tom’s girth. Obviously, it had...

1 year ago
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Jenny 2

We find our ladies in a lusty embrace out in the garden looking very dishevelled but amazingly sexy. Susan drew back from Jenny, giggling as she looked down at their clothes, soaked in hot piss, ruined stockings and shoes but the two friends had both satisfied their lusty desires in a most sensual way.“I think we had better go in and change don’t you darling” Susan enquiredJenny just giggled and said, “I think so darling, but doesn’t it feel lovely soaking ourselves like this” the ladies...

4 years ago
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Jenny and her Grandpa

Doug answered the phone, it was his daughter, Helen asking if she and his granddaughter, Jenny, could stay for a night in a couple of weeks. Jenny had applied for University in the town that Doug lived and needed to have a look round and speak with some of the lecturers etc. Doug agreed, he hadn’t seen much of either his daughter or his granddaughter in the years since his wife had passed away and it would be nice to catch up with them face to face rather than via E Mail every fortnight or so...

4 years ago
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Jennys dark secret total domination

Jenny had her pick of men prior to marriage, she stood out her statuesque physique, and her naughty sense of humor.When Jenny married, many felt it was for money, he was older, domineering and using their marriage, he dominated her and changed her personality, her forbidden fruits, once denied to many, were now available, as her sick husband turned 'Cuckold' and gave her away to men, only seeking pleasure watching them sexually abusing her, for denying them earlier in her life.Jenny told me of...

4 years ago
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Jenny and JohnChapter 3 Prom Night

I parked the car in front of Jenny’s apartment building at the appointed time, got out of the car, and waited as she asked me to. A few minutes later, a beautiful young woman came out the door and smiled at me. I could not believe how terrific she looked. I had not seen her with her hair done and full make-up before. The white gown we had bought looked even more perfect on her now. I stood there in my tux with my mouth open again. Jenny walked up and said, “You look nice, John, but you need...

2 years ago
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JennyChapter 8

Jenny and Ingrid were enjoying the last minutes of their "girls' night out" as they sat in Ingrid's great room and enjoyed a glass of wine. Jenny had told Ingrid of her desire for to become pregnant and she and Tom were hoping they would know soon. She had also shared her concerns over Tom's intervention on Vinnie's behalf. While the incident turned out well, she sensed Tom had taken some personal risks that might have put him in danger. Tom had brushed the confrontation off, but Jenny...

4 years ago
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Jenny Episode 1 Lesbians Caught

Introduction: Jenny is a gorgeous size 0 lesbian. She wouldnt dream of having sex with a guy! Untill a special friend come to her Jenny felt her pussy begin to swell as Kate stepped towards her. Kate was completely naked with size 32 D cups. She had the perfect breasts. Her cute pink nipples hardened as Jenny stared at them. Her pussy was bare. Waxed. It began leaking her sweet juices down her legs. Your a fucking slut, you know that babe? Jenny said as she stepped towards her friend. I had to...

3 years ago
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Jenny Ch 08

This is the final chapter in my re-post of Jenny, a story written over two years ago when I was just starting. I have edited it to improve the punctuation, grammar and, I hope, the readability. * Jenny and Ingrid were enjoying the last minutes of their ‘girls’ night out’ as they sat in Ingrid’s great room and enjoyed a glass of wine. Jenny had told Ingrid of her desire for to become pregnant and she and Tom were hoping they would know soon. She had also shared her concerns over Tom’s...

2 years ago
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JennyChapter 3

Nikki had calmed down and was sitting in a chair beside her mother with her towel wrapped around her. She was watching Tom string a floating white rope across the shallow end of the pool at the three foot depth. It would serve to mark Nikki's safe area and prevent the floater from moving into the deeper area. She had recovered from her fright and was waiting to get back into the pool. "Good for her," Tom thought to himself. Tom bent down to whisper in Jenny's ear. "Jenny, why don't...

1 year ago
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Jenny and I2

Jenny flopped back into the position she had been in for our previous fuck, and I moved between her legs. She raised her knees and spread them as far as she could. That gave me a direct shot at her cunt, and I had no trouble finding the right place to put my cock this time.Ever mindful of the hints that I had received from the previous time, I rubbed my cock head up and down in her pussy slit to make sure that it was wet with her lubricating oil. Jenny was dripping liquid from her cunt hole, so...

2 years ago
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jenny the teenage robot xj9

Jenny said to Tucker and Brad”guys run now it’s too dangerous here”. They replied back in unison “ok whatever you say” and ran like cowards behind a car. During the fight between the suit and Jenny the suit jumped off of rhino and onto jenny and sprayed a pink power onto her. In no less that 2 seconds jenny ripped off the suit. The suit slithered out of her mouth “you will need me soon more than you know it” with that the suit was taken to her mother to be disconnected. The next day she...

4 years ago
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Jenny Pt 1 Jennys Bad Day

Her answering machine beeped as it began to record. Hello, Jenny—I'm on my way over. As soon as I finish speaking you're going to do three things. First, you're going to unlock and unlatch your door—I don't even want to have to turn the doorknob, understand? Next, you're going to get out all of our toys and arrange them in a semi-circle just inside the doorway so that the door doesn't touch them when it opens. And when that's done, the last thing you're going to kneel inside the...

2 years ago
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Jenny Ch 05

This is a re-post of an original story from 2007. It has been re-edited for punctuation, grammar and readability. I hope I was successful. * Their wedding took place in the little United Church at the west end of the Village on a sunny Saturday afternoon in October. Jenny’s parents had come from Calgary a few days earlier, and were staying with Tony and Louise at the Blanton house. The two sets of parents had taken an instant liking to each other and were getting along famously. Perhaps,...

2 years ago
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Jenny and I4

Janice was a bit tentative at first, but I let her set the pace since she was paying for it. I wish I could say that it was my great technique that moved us along fairly rapidly, but, in all honesty, I must admit that Janice proved to be very horny when she warmed up a bit.Janice took her own blouse off simply because I was trying not to push her too hard, but it took less than 10 minutes for us both to be naked from the waist up and locked in a lovers' embrace. Neither one of us needed...

4 years ago
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Jenny Tanya and friends

Mike was in touch with Jenny again, they spoke on the phone and arranged to meet at a Coffee shop in town, Jenny had asked if she could bring her house-mate Tanya with her, Mike had agreed and then told her that as usual he would like to see them both in the clothes that she wore for him to turn him on, specifically short pleated skirt buttoned white blouse and high-heeled shoes. Jenny agreed then Mike asked that they both wear a school tie as well, and that they would be going to a friend's...

4 years ago
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Jenny and Her Ordeal

Jenny entered the room as the instructions had told her, she walked to the table and immediately began to undress; in front of her on the table she noticed the items she was supposed wear. She shuddered inwardly as her eyes took in the items on the table, she wondered how the hell the purchaser of these items had managed to find her size and if indeed the items would actually fit. As she let her blouse drop into the basket, a strange thought ran through her mind, would she ever see these items...

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