The Softening Of Jessie (Part 18) free porn video

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"So you want to know about different kinds of panties, do ya?" Ashley asked her inquisitive friend. "Yes, you might think it's kind of weird, but I seem to have forgotten. I know I wear panties everyday, but I guess I never paid attention," Jessie replied. He felt a little odd not knowing about something he felt he should have. "Okay, let's see...these are called boy short panties. They are just like the boring old underwear boys wear, but they are frilly'd and lacy'd up a bit," Ashley stated as she held up the almost see through panties, which were basically interwoven purple lace. "I like those. The design on them looks cool!" Jessie said as he admired the feminine lace pattern. "Yeah, it does look pretty cool. Now these are similar to what you are wearing, only they are sexier," Ashley said as she held up some mid rise peach colored panties which had tiny flowers stitched across the top and tiny flower patterns dispersed around. "These are for when you want to feel sexy and if you get lucky they will really turn on your ummmm... girlfriend." "Yeah, I could see myself in those. I'd have to beat the ladies off me if they saw me sporting those babies," Jessie modestly stated. "Oh yeah sweetie, the girls would just love those panties giggle. These my dear are called a thong," Ashley stated as she displayed the pink thong panties which had a white teddy bear eating a lollipop imprinted on the front. "Wow, those don't look very comfortable. Isn't that like a giant wedgie all day?" "Yeah, but you get used to it. You will probably be wearing thongs a lot. The last thing you want when you are wearing tight pants or whatever is to be showing a panty line. A thong is the best of both worlds...you have the comfort of wearing a panty without the lines," Ashley informed Jessie. "I get it I guess. I like the bear on the front though...it's fun." "So how about I buy you two pairs of each panty then?" Ashley offered her effeminate friend. "That's very generous of you Ashley. I couldn't ask that much of you." "It's alright Jessie. I want to do it. I have really grown fond of you, so please let me spoil you a bit." "Ok, you twisted my arm haha," Jessie replied as his new close friend paid for the bras and panties and handed him the pink Victoria's Secret bag. "Have a great day shopping ladies," the salesgirl said as the two left the store. Jessie gave the woman an odd look for a moment. He felt that what she had said was not correct, but couldn't place why it was wrong. He picked his brain for a second trying to figure out why her statement didn't feel right, but couldn't find an answer. Maybe it was just her tone or something. He smiled back at her acknowledging her farewell and the two went on their way. Ashley noticed that Jessie was taken aback a little by the salesgirl calling him a lady, but saw that he let it go as well. She wondered if he was becoming desensitized to the feminine pronouns being thrown at him as well. "So I have an idea...tell me what you think. What about getting your ears pierced?" "My ears pierced? No way Ashley! I think guys who have their ears pierced look gay. I'm no fag so I'll pass on that one. Any other ideas?" Jessie adamantly replied. "Oh come on Jessie. Don't be so old fashioned grandpa. Tons of guys have their ears pierced nowadays." "I said no... do I look a little loose in the loafers to you???" Ashley almost burst out laughing at his question. He didn't look loose in the loafers, he looked like he should be completely out of the loafers and in a nice pair of heels! "I'm upset Jessie. I thought you trusted my judgment. I even bought you some new bras and panties and you're going to treat me like this? I thought we were friends?" "We are friends...it's just that...well, you think I wouldn't look too gay in earrings?" Jessie asked giving in a bit. "Honey, earrings will not make you gay at all. In fact, they will make you even more attractive to the opposite sex. If you don't like them then you can take them out and they will heal over, so you have nothing to lose really," Ashley explained. "Okay, let's do it then. Hurry before I change my mind." Ashley grabbed Jessie's manicured hand and led him into Claire's. She showed him the different earrings to choose from. "I'll buy you whatever set you want Jessie. Try to keep it under $30 though haha." Jessie surveyed the earrings, admiring the selection. The studs were nice, as were the symbols and animal earrings. The one that stood out to him though was a small gold flower with a diamond for the center. "I like the flower one right there." "Oh I like that one too. You have great taste Sweetie." "Can I help you two?" the salesgirl asked the two girls. "Yeah, I want to get my friend's ears pierced," Ashley answered. "OK, first time?" "Yeah, first time for me," Jessie replied. "Which earrings do you want?" "The flower ones with the diamond center." "Those are the most popular. Go ahead and have a seat over there and I'll be right out." Jessie and Ashley headed over to the chair. As Jessie sat down the magnitude of what he was doing hit him. He was getting his ears pierced by a sharp needle and he began to panic. "I'm having second thoughts about this Ashley...this is going to hurt." "It's okay sweetie, it'll be quick and I'll be right here, alright?" Jessie tried to hold back the tears, but he couldn't stop his eyes from welling up. The tears began rolling down his cheeks as the moment of truth arrived. The salesgirl noticed the frightened girl as she approached the chair. "You feeling a bit scared?" the salesgirl asked. "Yeah, I think it's going to really hurt," Jessie replied as he tried to wipe the tears which streamed from his delicate eyes. "It will take less than a second honey. I have 3 piercings in each ear and I am the biggest wuss there is, so if I can do it so can you. I have Christina helping me out so that we can do both ears at the same time, okay?" "Okay." The girls aligned the earring guns to Jessie's ears as he closed his eyes which still flowed with tears. He was wondering why he had become such a cry baby lately...ummm, because this was going to really hurt?!? Pop! The guns shot the flower earring through his lobes and in a split second it was over. Did it really happen that fast? Wow! "You're all done!" the salesgirl announced. "That's it??? That didn't hurt at all!" Jessie gleamed. "I told you it wouldn't hurt, girl. Just make sure you sanitize them daily for the next 6 weeks," the salesgirl replied. "Oh I will!" Jessie promised as he admired his earring in the handheld mirror. Ashley couldn't help but notice that Jessie didn't even flinch when he was addressed as "girl". First the panties and now this...he was unaware that being called a girl or a lady was not correct. She had to test this further though to insure it wasn't a fluke. "Wow Jessie, you were such a brave girl! Your earrings look incredible too!" "Thanks Ashley and I'm sorry for being such a cry baby." "It's quite alright. First piercings are always rough. You were a brave girl." As Ashley paid for the earrings Jessie wondered out of the store in deep thought. Something wasn't right, but he just couldn't place his finger on it. What could it be? He was picking his brain trying to figure out where this deep rooted uncomfortable ness came from when suddenly WHACK! An elderly couple pushing a mall shopping cart ran straight into Jessie hitting his right knee, which caused him a considerable amount of pain. "Ohhh Ouch!" he cried as he bent down to grab his knee. "Why don't you watch where you're going?" he angrily yelled at the elderly couple. They should be glad that they are old, or else he would have pounded the guy into the pavement. As he grimaced in pain the tears once again began to uncontrollably flow. "We're sorry young lady, but we didn't see you. I hope you're all right dear," the old woman sympathetically stated. "Hey, are you OK? What happened?" a strange boy intervened. Wait, it wasn't a stranger, but instead it was the boy who was so nice to Jessie earlier that day. He was the only boy who didn't want to kick his butt for being with such a pretty girl as Ashley.

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The two began heading out when Jessie realized that he did not have his wallet. "Hey Ashley, how the heck do I carry my wallet? There aren't any pockets in this dress." "Yep, most dresses and skirts don't have pockets," Ashley replied. "I have something that will help," Jessie's mom said. She left the room and came back a minute later with a small light peach colored purse. "Put your stuff in here and carry it along." "Cool. I could put some cool stuff in here," Jessie...

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Amanda crept into Jessie's room and reached over to turn off his alarm clock. "It's ok honey, go back to sleep...you're not going back to school until that infection goes down," she calmly explained to Jessie, who had woken up. He laid his head back down and drifted again off to sleep. Amanda eyed her son as he slept. He looked so peaceful, and dare she say happy? Although the idea of changing him into a female was extreme on all scales, she felt that this was the only solution to...

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Jessie grabbed the phone and gave Ashley a call. "What's up Ashley?" "Hey, I wanted to see if I could spend the night at your house. Jason is having some of his friends over and I don't want to be here with those boys." "Jason invited friends over for the night and didn't include me huh?" Jessie replied. He knew that his friendship with Jason was strained but it still hurt to be not included. "Yeah...sorry, but I'll hang out with you tonight. I promise I don't snore. Besides we...

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"What are you thinking Ashley?" Jessie asked. He knew she was always full of great ideas. "Well, seeing that you enjoy wearing your pantyhose so much, why don't we just buy you some shorts? Then you can keep your nylons on?" Ashley plainly stated. She knew it would not be hard to convince her feminine friend to take this leap. "I don't know. Are you sure you that people won't be able to tell I'm wearing pantyhose? I don't want to take the risk and look like a sissy, cause boys...

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The two headed over to the miniature putting course. Jessie was so happy with how the day was going so far. He was befuddled as to why he could not remember how throw a baseball, but the fact that Jason seemed to genuinely like him again more than made up for that. It was just like the old days again and he was hoping it would stay that way. "I'm going to use the restroom real quick," Jessie told Jason. "Oh ok. I'll join ya. I gotta go too," Jason responded. As they headed to the...

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"What did you buy mom?" Jessie asked with a sense of excitement. Amanda handed her son the bag, noticing his curiosity. Jessie pulled out some of the contents. He noticed three bras with underwear attached in matching colors. "Matching bras and underwear mom?" "Yes dear, I was lucky to find some underwear that came with the bras so that you match," Amanda replied as she made little attempt to hide the bra panty sets. In Jessie's state of mind she knew she would not have...

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"Okay sweetie sit down and let's do your makeup. I'm thinking of something smoldering with your eyes." "Cool. Don't do anything too drastic though." "Don't worry Jessica. You are in good hands." "Before I start I'm going to put your hair in some rollers. It will give you some added volume and really enhance your appearance." Ashley deftly rolled Jessie's hair into several curlers and marveled at how he didn't bat an eye at being put into curlers. He just took it with stride like...

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"Hey, they have a cool log ride here if you guys feel like it," Ashley stated to the other three. "Oh, like the one at Knott's?" "Similar on a smaller scale." "Cool! Let's go." The four headed over to the water ride weaving through the mass of people at the park. As they made their way through the crowd Jessie found himself falling a little behind. He didn't want to get lost from the other three but he kept bumping into people and getting stuck in front of others. Jessie...

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"Here Jessie, let me help you over to that bench," Scott said as he sent the elderly couple on their way. "Good thing I was walking by here... I was just in the nick of time!" he joked with Jessie. "Scott right? Thanks for stepping in there. I was about to go off on those two. The old guy should feel lucky I didn't pound him into the pavement!" Jessie emotionally replied. "Well you do have spunk, that's for sure," Scott stated. He found the whole feisty, tough girl thing a turn...

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Ashley came over a short time later. "Alright Jessica, are you ready to have some fun in the sun?" "Yes I am. You're still on that Jessica kick huh?" "Yep, I think it suits you," Ashley teased. "Sure it does...not!" Jessie replied. "So your mom is gonna drive us to the water park. I've got some sun screen but we need some towels and you're gonna need a swim suit." "Cool. I'll grab some towels and I have a swim suit," Jessie replied as he ran into the hall closet and grabbed...

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Ashley reached into her bag and pulled out a pair of white open toe heels and presented them to Jessie. "These will look good with your outfit. Why don't you try them on?" "I don't think so Ashley. You're not going to get me to wear heels... those are girl's shoes," Jessie replied. He was taken aback from the offer. "Oh come on Jess, you can't wear a pretty dress and sneakers! Get real sweety. You need to complete the outfit. Besides, these shoes will show off your pink toes...you...

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The two girls headed downstairs. "Well, look at you two. Very lovely!" Susan and Amanda commented. "Thanks!" "Jessica you look so grown up but don't you think that skirt is a bit short?" Susan asked. "Come on grandma. It's not that short. Besides, Ashley wears this outfit all the time." "She looks fine mom. How do you feel Jessica?" Amanda asked her son. She felt some guilt at that moment. A couple months ago he was a young man & now she was looking at a very feminine...

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"Wow Jessica, I can't believe how great that top looks on you." Ashley stated finding herself a tad jealous at the thought that he may look better in that shirt that she does. "My bra doesn't look silly?" "No sweety, that's how it's supposed to look. That's the style." "Yeah I know but I really don't want to ruin my chance with Jason. I don't think he knows I wear a bra & if he can see it through my shirt than he may call me a sissy again." "Honey, you have breasts and...

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"Mom, you must see Jessie's nails! Not only did he do a beautiful job on my toes and fingers but he also glossed his toenails with guess what? Yep, pretty rose!" "That is wonderful dear," Susan replied, "He is progressing as we had hoped. All that anger, mischief, and all around bad attitude is giving way to a beautiful, blossoming child." "I just had the best time with him since...well, since I can remember. We actually bonded which is something I had all but given up on,"...

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Watching Jessie part 8

Watching Jessie (part 8)Frank was in the bedroom with Jessie when I got home from work on Friday. He hadn’t been over since last week. Now that he had Jessie pregnant I wondered if he was working on getting someone else pregnant. I was happy knowing that his wife Terry had given me an awesome blow job in the very same room at lunch time. Even though I didn’t get to fuck Terry I knew it was only a matter of time. I felt my cock getting hard as I thought about Terry’s beautiful black body and...

3 years ago
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A Delicious Jessie Sandwich

No girl has impacted me like my friend Jessie, and no sexual experience has affected my life more than the one I shared with her on December 26, 2013. Yes, we did slip up earlier that year when I took her in during a snow storm. It wasn't our intention, but we ended up having sex that night, the result of nearly 10 years of unresolved sexual tension. By then, Jessie had been married for a little while, so we both knew it was wrong and swore to never let it happen again. We meant it too, so I...

2 years ago
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Jessie Hanks Outlaw Queen The Cameo Murder Part 2 of 2

Street and Smith's _New_ _York_ _Weekly_ is proud to present the latest addition to the amazing legend of Eerie, Arizona. Jessie Hanks Outlaw Queen: The Cameo Murder By Nicholas Varrick As Told by Ellie Dauber and Christopher Leeson © 2016 Part 2: Finding Their Way Chapter 6 - "Crossing Arizona" Friday, June 7, 1872 Jessie slowly - regretfully - opened her eyes. "Uhh," she moaned, putting her hand to her head. "Why the...

3 years ago
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Jessie and the TornadoChapter 5

And back to the present Distantly I heard someone saying, “Sam? Sam? Sam?” then felt someone shaking my shoulder. I looked up, and realized I was still sitting outside Jessie’s hospital room, and that Janice had been trying to get my attention, before finally having to shake my shoulder. Jessie was standing beside Janice and was grinning like crazy. She had a small bandage on her forehead. “The doctor has finished his exam, Sam, and there is no sign of physical ... or mental problems,”...

2 years ago
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A Delicious Jessie Sandwich1

What neither one of us anticipated was that Brian, Jessie's husband would be one to share. Then came that fateful date, when the couple, who had moved away not long after Jessie and I slept together, was back home visiting family for the holidays. It was six months after Jessie had a baby, which, if nothing else did, seemed to rule out any possibility that we would stumble again. There wasn't possibly a scenario that would serve nothing better than ruining someone's life. Still, Jessie...

2 years ago
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THP JESSIE LISA AND ARON PART1

1.01 The House of Pleasure THP: 1.02 Jessie, Lisa, Aron: 1.03 Jessie, Lisa, Aron, HDTV Condition: 1.04 Mira, Jessie, Introduction: 1.05 Mira, Jessie, First Lesbian Orgasm: 1.06 Mira, Jessie, Jacuzzi: 1.07 Lisa, Aron, Hair Removal: 1.08 Lisa, Aron, Deepthroat: 1.09 Lisa, Aron, Sibling Mating: 1.01 The House of Pleasure THP: The House of Pleasure, THP, is a high end, sexual complex in the Center of Bangkok. It opened two years ago and has become a must layover for business...

3 years ago
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JAKOB JESSIE PART 6RAPE RETRIBUTION

Jakob, Jessie, and Sandy took a break for lunch on Sunday. They were covered in saliva, cum and pussy juice--sticky in most places. After showering together, Jakob fired up the grill while the girls made some burgers. Jessie brought them out to Jakob wearing absolutely nothing-her tan lines disappearing since she started sunbathing nude. Jakob admired her lean features accentuated by her large firm breasts that seemed more suited for a much heavier woman. He noticed her nipples were...

4 years ago
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Jakob and Jessie Part 4

From the minute he’d gotten the Sheriff’s phone call Jakob had known what he had to do. It was like killing a rabid dog or the feral hogs that had threatened his father’s stock. It was either kill Howard Holmes or live their lives in fear—fear that he’d get out of prison and hunt them down to wreak his “revenge.” In the end he’d done what he had to. He had rescued Jessie, his wife of less than a day, from a certain death at the hands of her father. Jakob had carried Jessie, insisting she...

2 years ago
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Jessie Hanks Outlaw Queen The Cameo Murder Part 1

Street and Smith's _New_ _York_ _Weekly_ is proud to present the latest addition to the amazing legend of Eerie, Arizona. Jessie Hanks Outlaw Queen: The Cameo Murder By Nicholas Varrick As Told by Ellie Dauber and Christopher Leeson © 2016 Part 1: On the Trail to Trouble Chapter 1 -- "Prolog: September 1871" Tuesday, September 12, 1871 A chunky, sandy-haired man walked into the Prescott, Arizona...

1 year ago
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Jessie Part 2

Jessie and I had a “normal” date Thursday night, dinner and a movie. When we left Emily with the her babysitter, Emily was disappointed that we were not taking her with us. Jessie had to remind her that the 3 of us were going to the zoo on Saturday. The movie was a romantic comedy which Jessie had picked. The movie was ok, however the plot was very predictable. At least I got to be with Jessie. I had my arm around her throughout the movie and we kissed a couple of times, however the theatre...

2 years ago
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THP JESSIE LISA AND ARON PART2

2.01 Sara, Jessie, Canine, Mounting Frame Preparation: 2.02 Sara, Jessie, Canine, Frame Deepthroat: 2.03 Sara, Jessie, Canine, The Mounting: 2.04 Aron, Extractor and Enhancer: 2.05 Aron, Jessie, Mother and Son Mating: 2.06 Lisa, Golden, Bedroom Services: 2.07 Aron, Creatures, Bedroom Services: 2.01 Sara, Jessie, Canine, Mounting Frame Preparation: Sara knew Jessie was ready and walked her toward the mounting frame. Without hesitating, Jessie entered the frame, kneeled down and...

4 years ago
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Watching Jessie part 9 breeding Amy

Watching Jessie (part 9)It was late Sunday night. I wanted to feel Jessie’s pussy on my cock. Tyson and Darin had just left. They had been fucking her for over eight hours almost nonstop. She had taken ten loads of cum. Her pussy was stretched out and overflowing cum. When I got in the bedroom Jessie was lying on the bed almost passed out. She had moved out of the pool of cum she had made on the edge of the bed. Another wet spot was growing from her pussy where she now lay. I stripped quickly...

4 years ago
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A Delicious Jessie Sandwich

Introduction: The following is an account of my long-awaited first sexual encounter with my friend Jessie, coming with a wild twist. Some details are exaggerated for the enjoyment of the reader, but the integrity remains. Also, in the same interest, preparatory and hygienic details were omitted. The shot glass shook in my hand as I endured the most awkward 10 minutes of my life. Ive never been a drinker, but the alcohol was needed tonight to calm my nerves as I sat across the glass coffee table...

3 years ago
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Jessie Hanks Outlaw Queen

Street and Smith's _New York Weekly_ is proud to present the latest addition to the amazing legend of Eerie, Arizona. Jessie Hanks -- Outlaw Queen By Nicholas Varrick As Told To Ellie Dauber and Chris Leeson (c) 2003 Chapter 1 -- "Riders in the Night" "One... Two... Three!" Jessie Hanks yelled, as she swung the saddle back and forth, then upward. This time, it worked. The heavy saddle went over the top of the tethered horse, settling unevenly on the blanket on its...

2 years ago
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Jessie The Tornado Ch 05

Again, I suggest reading the first four chapters before beginning this one. Also, I want to emphasize that if you are expecting a story with non-stop sex, then you will be disappointed. Jessie & the Tornado, Ch. 5 Distantly I heard someone saying, ‘Sam? Sam? Sam?’ then felt someone shaking my shoulder. I looked up, and realized I was still sitting outside Jessie’s hospital room, and that Janice had been trying to get my attention, before finally having to shake my shoulder. Jessie was...

3 years ago
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Jessie is pregnant Jessies revenge

(5th in a series)I had by now excepted the fact that my wife, (Jessie) was going to get or already was pregnant with my bosses (Frank) baby. I was partially to blame for encouraging her to fuck other guys but I didn’t expect her to take their semen. Not only was she letting Frank fill her with his semen but Jessie wanted to have Frank’s baby. Jessie’s once tight pussy was now always gapped open her pussy lips stretched and loose from taking Frank’s BBC almost daily and sometimes multiple times...

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