Watching Jessie (part 7) free porn video

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Watching Jessie

It was Wednesday before lunch time when Terry. Who was Frank my bosses wife walked into my office and shut the door. She was a hot sexy black woman. I stood up from my desk as she said “hi sugar". I couldn’t help but stare at her in her short tight red dress. Terry knew that I liked looking at her.
Terry started to tease me for spending Saturday night with her husband instead of her. I responded by saying that I would have much rather been with her but I didn’t think Frank would like that. She said “you shouldn’t worry so much about what Frank would like, do you think he worries about your feelings?”.
Terry had moved close to me. I was trying to understand what she meant, when she grabbed my belt and pulled me to her. My cock jumped to attention from her grabbing me. She ran her other hand down across my bulge. She then pushed me back into my chair and sat down on my lap.
Terry’s short dress rode up her round black ass as she rubbed against my stiffening cock. I put my hands on her smooth thighs. I could feel the heat from her pussy through my pants as she rubbed it against my cock. I was trying to figure out how to release my cock. Terry stood up and moved away from me pulling her dress down over her shapely ass as she did.
Terry told me that she wasn’t that easy. If I wanted her I’d have to earn it. She wanted to be wooed. Then she said “silly me” as she pulled her panties out of her purse and put them on. I asked how I was supposed to do that. I didn’t even have her number. She said if I was serious I would figure it out, and went out the door.
I certainly wouldn’t ask Frank for his wife’s number. Then it hit me. The emergency contact list Frank must be on there too. I pulled up the file and sure enough. Terry was his primary and both her mobile and home numbers were there. I entered them into my phone. I would text her later after Monica her lunch date got back to the office.
I looked down at my pants. There was a wet smear. I knew that it wasn’t all from me and smiled to myself.
I then went to catch up on my hidden camera in my bedroom. Jessie didn’t get up until about 10:30. She went in the bathroom with her phone. She returned a few minutes later and stripped off her nighty. As Jessie turned to go to her dresser I got a good view of her nipples. Still swollen and dark red from the guy who had been there yesterday morning. She put on a bra and a short dress but no panties and left the bedroom.
I was caught up with the video and my lunch hour was almost over. Jessie hadn’t been back in the bedroom. I decided to text her to ask how her day was going. Curious as to what she had been doing. I got no response at least for several minutes. Jessie returned to the bedroom in just her bra and went into the bathroom. Moments later I got a text from her “sorry I took so long Frank was here”.
I was thinking about how Terry had said that she wanted to be wooed. I decided to send Amy a message through Facebook since I didn’t know how else to reach her. I asked her how she was doing. I had given up on her responding. I was out on the floor when I got her message “scared". Then another message “are you sure Frank came in me “. I sent her my number so she could text me. I immediately got a text from her saying that I didn’t answer her question. I saved her number and responded “YES”. Then I sent her another “I’m sorry”.
Monica finally got back from lunch. I sent Terry a text to let her know that I had her number. She responded “Ok". I then asked her if she was free for lunch tomorrow. She sent back “I might be but only if you call and ask me”.
I was trying to get back to my office so I could call Terry. Devin and Tyson had me hemmed up and were talking smack, as usual. Ever since they helped Jessie and I move, they couldn’t help but offer to come over. They would show Jessie what a real man could do. How I was to scared cause I knew once she went black she wouldn’t go back.
I was finally back in my office and called Terry. I asked if I could take her to lunch tomorrow. She said that before she would agree I had to be honest with her. I said of course not sure where she was going with this. She asked me if Frank was having sex with my wife. I didn’t know what to say I’d just told her that I would be honest but I never dreamed that she would ask me that. There was a long pause before she said that she was okay with it. I just wanted to see if you’d lie to me. I then asked “you knew”. Terry didn’t answer but asked if I was looking for revenge with her. I realized what she was asking and answered no that she is incredibly sexy and that’s why I want to spend time with her.
Terry was satisfied with my answer. Which was basically true the fact that she was Frank’s wife was also a bonus. Terry said that she would meet me at the Palm’s restaurant near the mall. She wouldn’t be comfortable meeting me at work to go with me.
I had found something in Jessie and I’s prenuptial agreement. Sure I had to give her $6000 a month if I divorced her regardless of the reason. I also, after reading it over and over and even taking it to a lawyer, found that if Jessie divorced me it wouldn’t apply.
I couldn’t wait until tomorrow. I had a hard on thinking about Terry in her short tight sexy red dress. And how much I wanted to bang her gorgeous ass until I filled her married pussy with my cum
Amy sent me another text “are you sure you didn’t cum in me". I replied “no although I wish I did". Amy said “it’s okay if you did”. Again I sent “I didn’t…but I want to “. Amy sent me a bushing emoji.
Thursday morning seemed to drag on forever. Until 10:00 when I pulled up my video feed on my phone. Jessie was out of bed as soon as I left at 7:30. It was 10 minutes later that she came in the bedroom with the white guy from Tuesday. She was already naked and he was trying to suck on her nipples as she walked to the bed.
Jessie sat down on the edge of the bed. While he sucked her nipples Jessie undid his pants and pulled them down with his underwear. As he removed his pants and underwear Jessie slid off the bed. She grabbed his cock with both hands and took it into her mouth.
Jessie had been sucking on his long white cock for several minutes when he pulled away from her. Jessie got to her feet and leaned over the bed. The guy had a condom in his hand as Jessie waited ass up and feet spread apart. There was a pause then the guy tossed the condom aside. He put one hand on her ass and gripped his cock with the other. His cock disappeared slowly into Jessie.
Jessie’s ass lifted up with every thrust from her secret man. Her feet were now in the air. The guy grabbed her shoulders to pull her to him as he slammed into her pussy.
My own cock was hard now watching Jessie. It brought back visions of the first time that I watched her get fucked by another guy. That had been in a parking lot on the hood of a car. Jessie had been leaned over the car. This time though there was no protests from Jessie. She was eager to have this guys bare cock pump her pussy full of his cum.
My cock was rock hard as I watched Jessie getting fucked. The guy pulled his cock out as Jessie’s feet returned to the floor. Cum ran out of her pussy when his cock came out. Jessie went to the bathroom. The guy followed her.
It was several minutes before they returned to the bedroom and got on the bed. They began making out laying on the bed. I had to stop watching though for now and do some work before my lunch date with Terry.
I was disappointed that Terry had dressed very modestly, in slacks and a top that revealed nothing. We got a table and Terry sat across from me. It felt like a business meeting rather than a date.
Terry told me about her and Frank’s relationship. She had her tubes tied when their second c***d who was supposed to be a boy was born by c-section. Frank didn’t want to adopt. So she had a tubal reversal years later because Frank really wanted a son. For two years Frank tried daily to get her pregnant but with no success.
Terry was sick of sex by the time Frank gave up. They had tried to use a surrogate mother for Frank to have his own son. He had two more daughters who are with there Mother’s and he pays c***d support.
It was five years ago that Terry and Frank agreed to let Frank seek out women to get pregnant. They had not had sex since then. Terry had developed a couple of lesbian relationships since to fulfill her sexual needs.
Two years ago Frank had found a couple that wanted to have his baby. Frank had sex with the wife daily for months but couldn’t get her pregnant. He went to the doctor to get checked out and found that he had plenty of sperm. When he asked her to do the same. The couple finally confessed to not really wanting his baby.
I now doubted that Terry was looking for sex with me. I asked her what she wanted to do with me. Terry said that she wanted to spend time with me. She was interested in having sex with a man again. I asked what about Frank. Terry didn’t want to encourage him because honestly she didn’t want his monster cock destroying her.
I paid the check for lunch. Terry asked if I had time to go shopping with her before going back to work. Honestly I didn’t but I was still hopeful of getting to have sex with her. Especially if she hadn’t had sex with a man in five years. So I agreed to go shopping with her.
We walked to a high end department store. Terry wanted me to pick out a dress for her. I picked out a short blue dress with a low cut front and an open back. Terry tried on the dress and modeled it for me. It showed the top of her bra and barely covered her crotch. She didn’t have to ask if I liked it my smile gave me away. When Terry turned around I saw that her panties were showing in the low cut of the back.
I paid for the dress. Terry promised to wear it on our next date. If I wanted to see her again. Of course I wanted to see her again especially in the dress. Terry took my hand as we walked back to her car. She turned to me by her car and gave me a hug and brief kiss. Then told me to get back to work.
I didn’t have a chance to watch anymore of Jessie in the bedroom that day at work. When I got home Frank was already there. Frank and Jessie were in the bedroom having sex. I went into the other bedroom and watched the video from where I had left off.
Frank spent the night. I slept in the spare bedroom. I was woken up twice during the night to Jessie’s yelling yes yes fuck yes. Then again at 5:30 a.m. Frank left shortly after that.
Jessie came into see me when Frank left. She asked if I wanted to clean her pussy. I rolled over ignoring her request. Jessie slipped into bed with me and began stroking my cock. I wasn’t turned on but she wouldn’t stop. She started sucking my cock and eventually had me hard. She climbed on and put my cock into her sloppy pussy and rode me until we both came.
Jessie suggested that we go back our bedroom and rest for a couple of hours. She didn’t know what was wrong with her she just couldn’t get enough sex. We slept until we had to leave for our wedding.
I had lunch with Terry the following Tuesday again meeting her at the Palm’s. Terry requested a booth. She slid into the booth and patted the seat for me to sit next to her. I obliged her request. I couldn’t take my eyes off her breasts which were largely visible in the skimpy blue dress.
I hadn’t even realized that my cock was hard until Terry ran her hand across it. Terry had crossed her legs when she sat down. I tried to apologize for being too horny. She was pleased that I was so turned on. She moved my hand to her leg. I felt her leg. Eventually Terry uncrossed her legs after we had ordered our lunch.
I slid my hand up Terry’s inner thighs. She gripped my cock as my hand reached her pussy. She bit her lip as I rubbed her pussy through her panties. I worked her panties to the side. Just then our waiter returned with our drinks.
Terry recrossed her legs and let go of my cock. When she leaned forward to have a drink I placed my hand on the back of her neck. I slid my hand down across her bare back. She smiled at me as my hand reached the dress near her ass. I realized now that she wasn’t wearing a bra. My fingers played with the string of her thong.
Terry leaned back and I removed my hand from her back. I was staring at her breasts. She said “you like?” I replied “as far as I can see, they must be amazing”. I suggested that we go to her house after lunch. She couldn’t do that since it was only our second date. I countered that her sitting on my lap last Wednesday should count as a date. She laughed.
I was getting frustrated with Terry’s putting me off. I felt much better when we got up to leave. Terry took my hand and wrapped herself in my arm. She placed my hand on her hip. She put her arm around my waist. As we walked towards our cars I slid my hand to her ass and gave it a little squeeze. With her arm around my waist she tugged me to her.
Once we were by Terry’s car I turned her to face me. I kissed her full on the mouth she responded kissing me back wrapping her arms around my neck. Her tongue pushed into my mouth. She tasted like the pina colada she had been drinking. I pushed my tongue into her mouth and we continued kissing. Terry’s breasts were pressed against me. I began to feel my cock grow. After several minutes I slid my hands down her back to her ass. We continued to kiss passionately. I was feeling her ass but resisted the temptation to work her dress up and feel her ass without the dress covering it. She moved one hand from around my neck as we kissed and I massaged her ass. Terry slipped her hand between us and began feeling my cock.
My cock was fully hard. Terry’s dress was riding up. She broke the kiss and said we needed to get in the car. I went around to get in hoping that she wanted to take me to her house. When I got in Terry had her seat laid back. I leaned the passenger seat all the way back. Terry moved almost on top of me kissing me again. She had one hand on my cock. I pulled her dress up and felt her ass.
After several minutes Terry sat back in her seat. I moved across to kiss her more. This time my hand moved to her pussy. Terry was stroking my cock through my pants. I slid her panties aside and slipped my finger into her hot wet pussy. I found her clitorus and began working it with my finger. After a minute or two Terry stopped kissing me and started to moan.
As Terry moaned from my finger on her pussy I worked one of her breasts out of her dress. Her breast was soft and large. I moved my mouth to her breast. She moaned louder as I sucked her nipple. Suddenly she asked me to stop. I lifted my head from her breast still fingering her pussy. She said “next time…please”.
I remove my finger from her pussy and sat back in my seat. Terry asked when we could go to my place. I remembered that Jessie had a doctor’s appointment Friday that she wanted me to go to with her. I told Terry that we could go to my place Friday.
Terry worked her breast back into her dress. She kissed me again rubbing my hard cock. Then said “until Friday then.” We kissed for several minutes. Terry then told me I better leave because she didn’t want to lose control again.
Friday I called Jessie a half hour before her doctor’s appointment to tell her I wasn’t going to be able to make it. She should go without me. I left work and went out to the street where Terry was waiting for me. I got in and she drove to my apartment.
Jessie was just getting into her car when we arrived so Terry drove around the block. Terry and I finally got into the apartment. Terry was again wearing the blue dress I had bought for her.
I was already hard and Terry had noticed. Once in the apartment she backed up against me pressing my cock firmly to her ass. I pulled the hem of her dress up exposing her ass. She wasn’t wearing any panties. Terry turned around and we began kissing passionately while I massaged her ass.
We finally made our way to the bedroom. Terry was undoing my pants while we kissed. I was trying to remove her dress. Terry showed me how to get it off. Her breasts were awesome. I slid her dress down over her hips and she stepped out of it. Her skin was smooth as silk including her bald pussy.
We continued kissing. My hands running over her silky black beautiful body. I moved Terry onto the bed. She moved farther onto the bed, laying on her back. I got on the bed next to her kissing her my hand caressing her breasts. I moved my hand from her breasts down across her stomach to her silky pussy.
I caressed Terry’s pussy with my hand while kissing her. She was starting to moan. I moved my mouth down kissing her breasts before licking and sucking her nipples. Terry was moaning louder now but stopped to tell me to tongue her pussy. I was ready to strip and plunge my cock into her pussy.
I moved between Terry’s legs and began eating her pussy. I was listening to her as I tongued her pussy. She was moaning oh yes as I flicked her clit with my tongue. I kept it up since she really seemed to like it. My tongue tired so I plunged it into her pussy and sucked up her juice.
Terry had her hands on my head as I resumed flicking her clit with my tongue. I was running my finger in and out of her pussy at the same time. I felt her body tense. Terry moaned loudly and cried out as she pulled my head to her pussy. I felt a flood of juice on my finger. I moved my mouth down to suck up her juice.
I had Terry’s juice running down my chin when I finally moved from between her legs. Terry had me get off the bed and she pulled down my pants. Terry knelt in front of me and began sucking and stroking my cock. Terry now had one hand on my ass and one grabbing and massaging my balls. Slowly her mouth completely engulfed my cock. I could feel her tongue working on my cock. It felt amazing.
I warned Terry to stop before I came. Terry didn’t stop. Instead she started bobbing her head rapidly on my cock. She was gurgling as she continuously took my cock deep Into her throat. My balls were slapping against her chin. I couldn’t hold back anymore and started to cum. Terry kept the head of my cock in her mouth running her tongue around it. She had one hand squeezing my balls and the other one was stroking my cock.
Terry swallowed all of my cum. She stood up and commented what a huge amount of cum I’d fed her. My cock was still hard. I crouched down a little bit and pushed it between her legs. She kissed me as my cock rubbed against her pussy. I could feel the moisture and heat as my cock slid back and forth between her pussy lips. Finally my cock didn’t slide by. Before I could push more than the tip of my cock into her Terry stepped back. She said that she wasn’t ready for that now.
What to hell I thought to myself. I was surprised and unsure of what she meant. Terry was putting her dress on. I finally asked what she meant by ” she wasn’t ready now.” She explained that she was a little old fashioned she guessed, but she wanted to save that for next time. Besides she didn’t want to be here when Jessie came back.
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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...

4 years ago
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My Last Thought Was Jessie The Ending

My brother, Jessie and I had spent the entire week at home and pretty much naked. We had sex several times every day. I couldn’t help but be worried about our parents coming home. I didn’t know what to expect, because I was sure that my Dad knew what was going on, considering he caught Jessie and I in the pool house in the bed together wrapped in each others arms naked. “You are thinking about it again aren’t you?” Jessie was standing in the doorway of the living room. He was naked, but his...

Incest
4 years ago
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A Jessie McClintock Story SUCCUBUS PART 1

Jessie looked coolly at the man sitting across from her. She didn’t like him. Not his silk shirt, not his slicked back hair, not his fake tan. Gino the strip club owner. He was a walking stereotype. Her thoughts drifted mournfully to the Glade plug in working overtime in her office to combat this douchebag’s aggressive use of Axe body spray. Then she thumbed through the bundle of cash he’d tossed in her lap. “Look, I need this done, and I’m told you’re the only person to talk to...

2 years ago
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A Jessie McClintock Story SUCCUBUS

“So ya gonna take the job or not?”Jessie looked coolly at the man sitting across from her.  She didn’t like him.  Not his silk shirt, not his slicked back hair, not his fake tan.  Gino the strip club owner.  He was a walking stereotype.  Her thoughts drifted mournfully to the Glade plug in working overtime in her office to combat this douchebag’s aggressive use of Axe body spray.  Then she thumbed through the bundle of cash he’d tossed in her lap.“Look, I need this done, and I’m told you’re the...

Supernatural
2 years ago
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Jessie and Emily The Hunters Second and Third

I was driving to my favorite grocery store to stock up on essentials. I saw a blur appear in my peripheral vision and woke up two days later in the hospital. I had a broken leg, a broken wrist and a concussion. A delivery truck had run a red light and broadsided my car. Luckily for me, a policeman was witness to the accident and had quickly gotten an ambulance on the scene. Even better for me was the four moving violations issued to the driver of the truck. The company had sent a...

Hardcore
2 years ago
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Dance of a LifetimeChapter 116 Jessie Hits The Jackpot

"Hi, Soph!" Jess chirped. "Hello, Jessie," Sophia said, sitting down in the chair across from the couch. "Welcome home. Now, do you mind telling me why you're sitting in my fiancé's lap kissing him?" "I'm trying to get him into bed," she giggled. "Oh, that did not help," Warren moaned. Sophia's mind boggled. She was prepared to believe she had walked into something innocent-until Jessie said that. "You're trying to get Warren into bed," Sophia said. "What...

4 years ago
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My Last Thought Was Jessie The Homecoming

I hadn't been back in Florida for more than three days and I was already miserable.  I missed Jessie so bad.  It was like having a part of myself ripped away.  I wondered to myself how I had went this long without realizing how much I really loved him.  My mom had noticed my depression, but when she would ask me about it I refused to talk about it.  Part of me wanted to blame her, because she had left my father.  But when I would really sit down and think about it I knew that if she had stayed...

Incest
3 years ago
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Bent Over for Uncle Jessie

Mom's older brother, Jessie, was always a flirt and often thought he was God's gift to woman. He was always quite the womanizer and knew just how to work the scene, even given his advancing age. I could see this as he mingled with the large crowd of family on our huge deck at the family reunion mom had organized. I watched Uncle Jessie flow through the crowd of family eying female family members like they were just another woman. All of them smiled at him and he reveled in it. I just snickered...

Incest
2 years ago
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Mom and Uncle Jessie Their Story

I walked into the living room where mom had slunk down into the leather couch. She was worn out from hosting family members that only showed up once a year. Mom had changed into her night shirt and her 40 year old leathery legs jutted out from underneath the hem in tired fashion. I sat beside her and patted her on her bare knee."So, was Jessie everything you thought he would be?" Mom asked after I settled in beside her.I gave her a very peculiar look. I really did not know how to answer her....

Incest
1 year ago
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Jessie Fan Fiction

Jessie gasped seeing that Ravi's manhood was over 6 inches.             “Wow Ravi how long is it now?” Jessie asked walked forward and dropping to her knees.             “7 inches,” Ravi moaned as he felt Jessie’s young mouth engulf his meat.  Luke walked over to Jessie and started to suck on her left breast as he inched and played with her right one. Jessie moaned out load as she started to deep throat Ravi's cock.             “My gosh Luke" Our nanny is giving me such a good...

3 years ago
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Jessie

Jessie gasped seeing that Ravi's manhood was over 6 inches. “Wow Ravi how long is it now?” Jessie asked walked forward and dropping to her knees. “7 inches,” Ravi moaned as he felt Jessie’s young mouth engulf his meat. Luke walked over to Jessie and started to suck on her left breast as he inched and played with her right one. Jessie moaned out load as she started to deep throat Ravi's cock. “My gosh Luke" Our nanny is giving me such a good blow! Jessie pulled...

4 years ago
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The Softening of Jessie Part 10

Mom and grandma went upstairs to change out of their workout gear, as Jessie relaxed on the family room couch. That was quite the workout. He felt good about himself though. It had been a while since he did physical exercise, so it was nice to get back into a routine. The exercises themselves were far different from his usual lifting weights, but he enjoyed the cardio segments and the one which targeted the thighs and buttocks. Knock Knock Knock. Someone was at the door. Jessie was...

3 years ago
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Jessie and the TornadoChapter 4

When I woke up the next morning, the first thing I did was check my car. Jessie’s purse was gone. I noticed that her car was not in the driveway of her parent’s house, and one of her parent’s cars was also missing. I tried calling her cell phone over and over, but she never answered. I left a number of messages begging her to call. Now, all I could do was wait. Had she and her parents gone somewhere? Then why were two cars missing? I paced back and forth from one end of my house to the...

3 years ago
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Jessie The Tornado Ch 01

If you are looking for a story filled with sex, then you are probably in the wrong place. I don’t write sex stories. I (hopefully) write interesting stories that contain sex. Someone once said that women need a reason to have sex, while men only need a place. Like most generalities, I think that is generally wrong. I think that people need to have a reason to have sex and that if they care for each other, then the love and sex will be even better. All the participants are at least 18. The...

2 years ago
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How I Helped My Friend Jessie To Increase Her Boobs Size Part 8211 2

Hi everyone, I am Continuing my story… I looked at the time it was quarter past one. I went near her Me: How is your Leg Pain? Jessie: Now I feel little better. Me: You want me to massage again? J: No, No Need it is fine now. Me: Ok, then you feeling sleepy? J: No, But I want to sleep now. Because tomorrow after reaching home, has to go to my aunt house with my mum. Me: Ok, If you want to sleep you can sleep on my lap. She thought for a while and looking around to see others. Me: No one is...

2 years ago
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The Softening of Jessie Part 27

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...

4 years ago
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Jessie Babes Story

Thanks to FrenziedMaiden for her help and friendship. Jessie is a delicious girl. She lives with just her dad and idolizes him. She is not a virgin, but her partners have never satisfied her. They have never met her expectations. This is a story about how Jessie finds herself and everything she wants. Jessie was 22 and she had to admit that she looked good. Her boobs were high and tight, not too large, but pert and perfect for her figure. Her ass was just fine too. All in all, Jessie was...

2 years ago
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The Spftening of Jessie Part 11

Amanda felt like Jessie had enough excitement for the day. After his emotional outburst when Jason saw him clad in his girl's workout outfit, the voice change, and the trip to the nail salon, she took him home to relax. Jessie was thrilled with the way his nails looked. To think that he was so egotistical about how well he painted nails haha. Those women really taught him a lesson or two. As he admired his strawberry shimmery nails he wondered why black was always his favorite color....

3 years ago
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The Softening of Jessie Part 9

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...

3 years ago
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The Softening of Jessie Part 7

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...

4 years ago
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The Softening of Jessie Part 22

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...

3 years ago
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Dealing With JessieChapter 2

Jedd Clampett This is the second of a nine part story. Please read and comment on the content. Vote of you like. Here goes part two... Gary had always been her rock in tough times, her ever faithful husband, and the responsible father. Where had it all gone so wrong? He realized none of that mattered, not to her, not anymore. To her he wasn’t anything. He was like a spare part, something extra, a left over. Really, what could he offer; nothing now, nothing she couldn’t get from her...

3 years ago
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Watching Jessie part 10

Watching Jessie (part 10)Wednesday morning Terry texted me and said she would pick me up at 11:00. Darin, who had taken my wife to his place last night, still hadn’t gotten to work when I left. Terry was parked on the street waiting for me when I went out shortly before 11:00. It took me I while to see her as she was driving a Lexus SUV that I didn’t recognize.I got in and Terry drove us off. She had a long coat buttoned up as I wondered what she was wearing underneath. She pulled up to a gas...

4 years ago
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Jessie The Tornado Ch 04

Again, I suggest reading the first three 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. * When I woke up the next morning, the first thing I did was check my car. Jessie’s purse was gone. I had already noticed that her car was not in the driveway of her parent’s house, and one of her parent’s cars was also missing. I tried calling her cell phone over and over, but she never answered. I left a...

3 years ago
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The Softening of Jessie Part 16

"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...

3 years ago
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The Softening of Jessie Part 35

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...

4 years ago
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Dealing With JessieChapter 6

It was summer, and the days marched on. Jessie didn’t resign, but she turned all the household finances, though none of her money, over to Gary. He took the department head’s job at the high school. He put his house up for sale, and, being in an upscale low property tax suburb it went quickly. He bought a new sofa bed, a clothing rack, and a small bureau for the cellar. There was a small bathroom with a shower and basin so he wouldn’t have to go upstairs for any of that. Jessie signed up for...

3 years ago
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Dealing With JessieChapter 9

So it had off to Denny’s where they ate and went back home, where he’d been told someone had pooped in the pool. They’d gone to bed, had some more fun, and Jessie went to sleep. He didn’t; she was a lot sicker than he thought. He wondered if the psychiatrist knew more than he’d shared. Jessie’s comment about semen slurping almost pushed him over the edge. Edge of what he didn’t know; at the moment he was ready to just walk out but what really scared him had been her emotional disappearance....

3 years ago
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The Softening of Jessie Part 4

Jessie woke up in the afternoon the next day. Ahhhh, Saturday morning...no school, got to love it. He rolled out of bed and stretched a bit. The fabric of his "borrowed" delicate, soft top felt much nicer on his sore chest than his rough, course t-shirts. "Man, Jason really did a number on me," he thought. With that, Jessie groggily went into his bathroom, sat down and peed. It struck him a bit odd that he was sitting to pee. After all, he couldn't ever remember sitting down before to...

2 years ago
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The Softening of Jessie Part 13

"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...

4 years ago
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Jack Jessie part 2

Amy let herself into the house. She and Jessie had been friends since grade school, and knocking had fallen by the wayside. “Jess! Saw you were home alone, and came to hang out!” Amy was puzzled, there was part of a pizza on the coffee table, bottle of wine, and moaning coming from the back of the house. “OMG! She brought a boy over, and got her cherry popped!” Amy thought giddily. “I gotta sneak a peak, and see who it is.” So she quietly made her way down the hallway to Jessie’s room, and...

2 years ago
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The Softening of Jessie Part 17

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...

3 years ago
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The Softening of Jessie Part 18

"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,"...

3 years ago
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Teenaged Jessie enters my bed and my heart

Her mother was a drunk who was usually so plastered that she staggered around the house in her baggy house dress, falling over the furniture till she passed out. Her father was abusive, not sexually but he often hit her and pushed her around and verbally abused her. He frequently brought other women home to fuck while his wife was passed out on the couch. He did not pay any attention to his daughter being around. Several times she had seen him roughly throat fucking some slut that had...

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