The Softening Of Jessie (Part 22) free porn video

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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 could have lots of fun together," Ashley responded. "Yeah, there's no way. My mom would never let a girl stay over with me all night. She'd be too freaked out that I'd get into trouble...you shouldn't trust me either. I'm pretty much a magnet around the ladies," Jessie half joked. "Oh I see...I think I can handle you. Ask your mom," Ashley responded holding back a laugh. Jessie's masculine traits were all but gone and she didn't care for girls. "I'll ask but I already know what the answer is." Jessie called out to his mom. "Mom, Ashley wants to know if she can come over for the night." "She wants to spend the night?" Amanda asked. "Uh yeah. I told her that it's a dumb idea." "Well I think it might be alright. She's a nice girl." "Really? But she's a girl mom...and I'm a boy...do you follow me?" Jessie asked rather dumbfounded. "Yeah, I know. Just keep the door open then," Amanda replied to her very feminine son. Jessie scratched his head and picked up the phone. "She said it's cool. You can come over." "Awesome! I'll be by around 5 and I'll bring stuff to play with. We are going to have so much fun!" Ashley arrived at 5 with her duffel bag. The two ate dinner and chatted with Amanda and Susan for a while. Before long the two decided to head up to Jessie's room and get ready for bed. Jessie went into the bathroom in the hallway while Ashley used his bathroom to change into her pajamas. Ashley quickly put on her blue plaid sweats and yellow tank top and chilled on Jessie's bed. Jessie came in the room shortly after. "Wow, I'm stuffed from dinner. I think I could eat dessert still though," he stated. Jessie was donned in a light yellow nightgown made of nylon that came to rest just above his knees. It had a white lace trim around the shoulder straps and around the skirt. For all intensive purposes it was a dress. Ashley was amazed at what he was wearing and the fact that he didn't even realize that he was in such a feminine outfit. "I like your pajamas Jess." "Thanks, it's comfortable to sleep in." "Do you wear pantyhose to bed too?" Ashley asked noticing that his legs were still encased in sheer nylon. "Yeah...I just like the way they feel. Plus they keep my legs warm at night." "Yeah, you'll get tired of wearing them sooner or later." "So what do you want to do?" Jessie asked. He felt a little uncomfortable being in the same room with such a pretty girl. He always thought of himself as the man but his nerves were getting the better of him. "Well I think I should give you a makeover," Ashley replied as she pulled out her makeup box. "A makeover? What do you mean?" "Well you have to trust me ok? I want to have some fun with you." Jessie thought about her statement and gave in to her request. "Good, now sit back and let me do my work. First thing I want to do it trim your eyebrows a little. They are way too bushy girl," Ashley stated using the feminine pronoun. "Don't make me look silly ok?" "Oh I won't". Ashley pulled out the tweezers and had Jessie lay his head on her lap. He looked so cute in his nightee she thought. Jessie wasn't sure what to think. One part of him knew he should be in heaven to be so close to such a pretty girl, but the other part just felt very comfortable and relaxed. PLUCK. "Ouch," Jessie yelled. "Oh calm down ya big baby...no pain no gain," Ashley replied. PLUCK PLUCK PLUCK "That hurts Ashley," Jessie stated grimacing in pain. PLUCK PLUCK PLUCK PLUCK PLUCK PLUCK The plucking went on for what seemed like an eternity. In fact it was quite a while. Ashley's finished job resulted in very thin, highly arched brows which were unmistakably feminine. "Can I see?" Jessie asked. "No not yet, we are only getting started. You have to wait until I am finished," Ashley replied. She was amazed at how the plucked eyebrows made him look completely different...completely girly. Ashley opened up her makeup case and sat Jessie up. "I'm going to do your face up ok?" "Like what? A clown?" "Yeah, sort of...only not really...promise not to move ok?" "Ok, I can have a sense of humor about this." Ashley opened up her bottle of foundation and placed a bit on her sponge. She blotted it all over Jessie's face and smoothed it in with the sponge. "That stuff smells funny but good," Jessie stated. "I'm going to apply some powder now. It will give you skin a porcelain finish," Ashley replied as she used her brush to gently cover his face with the delicate powder. "Now I'm going to make you eyes look pretty. Close them please." Jessie reluctantly closed his eyes. He felt a brush sweep across his right eyelid and then his left. The brush then went back to his right eyelid and was brushed over it several times. The same was done to the left. The he felt what seemed like a wet felt tip pen trace over his upper right eyelid. The same was repeated on his left. "Open you eyes now," Ashley said as she used the eyeliner pen to line his lower eyes. "Now I want for you to look up at the ceiling and don't flinch...it's important that you don't move ok?" "OK." Jessie looked up as he saw a black wand with tiny bristles on it come close to his eyes and brush his upper eyelashes several times. It was uncomfortable and he wanted to move but did as Ashley requested and stayed still. She then took the brush and did the same to his lower lashes. Jessie somehow felt weird about what was happening. It didn't seem quite right but the more he tried to think of why it wasn't normal the more he drew a blank. "Perfect." He then saw her pull out what looked like a dark pencil. He felt the pencil trace his eyebrows. Ashley grabbed her red lipliner and began tracing Jessie's lips. Jessie was amazed at how good Ashley was at this. She seemed very confident and self assured. . As soon as Ashley traced his lips, Jessie saw her pull out a tube and pull off the top. She then twisted the base and a lighter red cylinder came to the surface. "Open you mouth a little....just like that" Ashley carefully but deftly applied the lipstick to Jessie's lips. "Now move your lips back and forth to smooth your lips over then blot them on this Kleenex." Jessie did as instructed and saw the red lip prints that were left on the tissue. "Wow, you look amazing!" Ashley said. She choked back a tear as she was stunned at how pretty and downright girly Jessie looked all made up. "You OK Ashley?" Jessie asked noticing her emotions. "Yeah, I'm fine. It's just that you look really great is all." "Now for the hair!" Ashley excitedly stated as she plugged in her curling iron. "You're going to curl my hair?" Jessie asked. "No, it just adds some volume and a few twists." She took the iron and curled his hair in several places then brushed it out. There was a lot of room to play with. His hair was beautiful and down to his shoulders. Ashley brushed out his hair and applied some hairspray to hold it in place. She stood back and admired her work. Jessie was all girl without a doubt. "Ok, go look at yourself Jess." Jessie got up and went to the bathroom and he momentarily lost his breath. "Wow, is that me?" he asked. He was amazed at how different he looked. His eyebrows were pencil thin...his lips red...his eyes outlined in black with a blue green tinge to his lids. "Yes, what do you think?" "I look really different," Jessie replied. There was something that wasn't right...what the heck was it? He couldn't place it... "But I like it!" "Really?!? I am rather good at makeup I have to admit," Ashley replied. "Yeah, I think it looks cool. Can you show me how to do it too?" "Yeah. I'm glad you like it. I can show you lots of cool tricks. Makeup is a lot of fun."

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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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Jessie sat on his bed looking at the new underwear his mom had bought him. Something wasn't quite right about it but he didn't know what. His mom was so supportive and understanding of his sensitive chest and his sudden weight gain in his lower section. He should be grateful that he has such a wonderful family. "What the heck. Let's try these bad boys on and see if they fit." Jessie stripped down and looked at the selection of underwear in front of him. The logical choice, he...

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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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"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,"...

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As the two sat at the food court eating lunch, Ashley couldn't help but how much her friend had changed. He now sat there with his nylon covered legs crossed in a very feminine manner and spoke with an unmistakable high girlish tone. Wow, how could he not know what was happening to him? "How does your bra feel Jess?" Ashley asked out of the blue. "It feels good. My chest doesn't jiggle all around like it was before. I think that the bra may actually help my swelling go away by...

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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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"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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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...

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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...

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...

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...

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...

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...

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...

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...

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...

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...

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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