Jess Michelle and Me Pt II
- 3 years ago
- 31
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My wife's friend Jess has been living with us for the last two months. She and her ex split and he basically threw her out on the street. She was living in her car until Michelle my wife talked me into letting her stay with us.
Now my wife is a straight-laced professional woman. Five foot-seven, one hundred ten pounds, long dark hair, and tits that stop traffic. She knows that every straight guy in the office would jump at the chance to bang her. Sometimes, I think she enjoys the attention a little too much.
Jessy has shoulder-length curly red hair, long skinny legs, her tits are a little smaller than Michelle's. A couple of tattoos and a really nice ass. But she's not my Michelle, and the thought of sex with her never really crossed my mind.
Now, Jess is the free spirit type. Meditation in the morning followed by some yoga and then off to work at the head shop. She sells drug paraphernalia and sex toys.
About the only thing that I have in common with Jess is we both like to partake in the electric lettuce. Michelle not so much. But Jess and I like to smoke some pot at the end of a long day.
After dinner one day, I was sitting on the back deck with Michelle. We were just talking about things while I was rolling one up and Jess came walking out with a drink for Michelle.
Michelle will have a drink once in a while but not very often. She and Jess were joking around and laughing while I smoked my joint, passing it off to Jess as we finishing it off. I got up to go get another beer.
When I came back both of them were really quiet. Just looking at each other with a funny smirk on their faces. I looked at them and Jess just started laughing. Not knowing the joke I asked what I missed.
Michelle just smiled and said "It's nothing. Girl stuff."
That stopped me from asking any more silly questions. Michelle got up and went inside. Jess sat back in her chair taking a couple of sips from her drink. Then she asked me a question that I wasn't expecting.
She looked over at me and asked, "Can I sleep with Michelle?"
I didn't know what to say. I rubbed my chin looked up and told her, "No."
"Why?" she asked with a look of disbelief.
"She wouldn't sleep with you," I replied. I know my wife. She'd never expressed interests in women before. Not even remotely. Not to me anyway.
Jess smirked, "Wanna find out?" then gave me a wink.
She was up to something. She never really expressed any sexual interests in Michelle or me, or anyone lately for that matter. But I think that she was feeling a little horny.
Michelle came back out asking what we were talking about now. I just sighed, and quietly told her that Jess wanted to sleep with her.
"Really?" Michelle's face lit up a little and her cheeks blushed. Looking over at Jess. She stammered for something to say that wouldn't make her sound like she wanted to, but not make it so obvious.
Michelle looked back at me and I repeated, "She asked me if she could sleep with you, and I said no."
Looking over at Jess then back to me she asked me why?
Her facial expression was of somewhat disappointment, and confusion.
"But you thought about it. Right?" she asked while taking a sip of her drink.
"Nope," I said, "I don't think you'd go for it,"
"In a heartbeat!" she blurted out.
Jess just looked at me like she knew all along.
"I would totally sleep with Jess! If and only if you would let me?" Michelle's tone was straight forward with no hesitation. She had a serious look on her face, one I've seen way too often.
"You can. But you have to share her with me. No exceptions" I wasn't going to miss out on this golden opportunity.
Michelle just clapped her hands with excitement. Then collected herself.
Jess just sat there grinning at me, looking over at Michelle, and then back to me. "Who goes first?"
I just raised my hand then pointed to her. "You can sweetie. But you have to do it right here right now."
Michelle didn't hesitate for a second. She eagerly turned to Jess and wrapped her arms around her and planted a passionate kiss on her lips. Jess returned the kiss looking over at me. Their hands started to work themselves lower to each other's breasts.
Jess leaned back and pulled her top off. Michelle started to kiss and lick at her nipples. Michelle slid her hand down between Jess's legs as she spread them open and started to unzip her cut-offs. Michelle helped her take them off and put her face right up close to Jess's pink slit and started to lick up and down. Jess placed her hand on the back of Michelle's head leaned back looked up and let out a slight moan. Pinching her own nipple and holding Michelle's head she closed her eyes bit her lips and started panting.
It didn't take long before my cock was starting to make my pants uncomfortable. So I unzipped them and let him get a view of the sight my eyes were taking in.
Jess was starting to breathe heavier as she started to pump her hips and pussy into my wife's willing mouth. Jess then opened her eyes looking at me. I got up and walked towards them. Pulling my cock out completely, I held it in front of Jess's face. She took in a deep breath, I wiped my cock on her cheek. She gave it a kiss and grabbing it with her hand stroking it softly. Her lips wrapped around my head. I could feel her tongue circle around it. Jess's mouth was so warm and wet as she took me in a little deeper each time.
I laid Jess flat on her back across the bench. Michelle was between her legs and her head hung off the edge. I started easing my cock in her mouth and down her throat. I didn't push too far too fast. Just to see how much she could take. Her hands went behind me as she pushed me into her throat. My balls slapped on her nose as she let a moan.
I grabbed ahold of Jess's nipples and tugged on them a little. She was moaning louder as she kept pushing at me to fo deeper in her mouth.
Michelle looked up at me and went right back to sucking on Jess's clit. Jess started to moan on my cock while Michelle worked her over with her mouth. Soon Jess couldn't take anymore and screamed out and flooded Michelle's face with her juices.
I jumped back as Jess came up howling, she slapped and rubbed her pussy. Then let out the biggest flood I'd ever seen. I sat behind her and cupped her breast as Michelle sucked on her nipples. Jess kept rubbing her pussy while panting hard, gasping for air.
Jess almost fell off the bench shaking when Michelle slid her fingers up in her pussy.
Jess couldn't control herself any longer as Michelle worked her over with her fingers and tongue. She let out a scream and squirted again all over the deck. Michelle backed off and slapped her ass.
I had never in my life seen a woman gush so much. It must have been all of that sexual frustration built up in her. Michelle had once told me that she wasn't satisfied with her ex at all. I was starting to wonder if this was a ploy by Jess to find out if she was a lesbian or just bi-curious.
Jess kissed Michelle passionately for a little while there. Michelle then took a towel and wiped her face. "My turn." She stood up and sat back in her chair. She then hiked up her skirt pulled her panties over and asked Jess if she could make her squirt.
Jess's face dove into Michelle's pussy without a second thought. I looked at my wife spread out on the chair with Jess licking at her pussy now. Making my way towards Michelle I kissed her and freed her tits from her bra. I sucked and pinched her nipples as I could feel them stiffen rapidly.
Now, I know that Michelle loves a cock in her mouth when she's getting stimulated. I've got some of the best head from her, while I fucked her with her favorite toy. I slid my cock over her lips this time. Her lips parted and her tongue licked my shaft and balls.
She took me in her mouth as Jess clamped her mouth to my wife's pussy. Michelle moaned bounced, her breathing was picking up as I could tell she was already close to her climax.
I let go of Michelle and looked down to see Jess's ass wiggle from side to side as she worked over Michelle's pussy with her tongue. I knelt down behind Jess and poked at her asshole with the head of my cock.
Michelle let me fuck her ass once but that was a long time ago. I didn't know if Jess would reject me or stop me. I tested her willingness and poked slightly at her. She didn't make any move to stop me. I licked at her ass and I heard her moan. I grabbed the base of my cock and slid it into Jess's ass.
Jess screamed and turned her head back towards me "Fuck!" Michelle grabbed her by her hair and before she could say another word shoved her face back between her legs. And wrapped her legs around it. I pushed a little bit further. Jess let out another muffled scream into Michelle's muff as I slid in further.
Michelle let up of her grip on Jess as her head whipped up and started panting. She looked at Michelle and turned back towards me trying to catch her breath. "Fuck my ass! Fuck it!" she screamed then slid her tongue back into Michelle.
My thrust was getting deeper and longer as Michelle started to scream "I'm cumming!" I came in Jess' ass. Jess looked up and came again. So hard I could feel her juices splatted on my balls.
We all looked at each other for a second. I wasn't sure what I should do next. I stood up and heard Jess say "Where you going?" I turned to her as she took me in her mouth, sucking hard and licking my balls until I was cleaned of both her and my cum.
Michelle got out of the chair, straightened out her dress, and told Jess to get cleaned up and meet her inside. Then, she walked into the house. Jess looked at me picking up her clothes. "Do you think she's mad?" she asked me.
"Go in and find out," I said.
Michelle came back out just after Jess went in. She walked over and sat down next to me. "Do we let her stay a little longer?"
I sat back in my chair. "Go have some fun, sweetie." As I put my hands behind my head and leaned back in my chair. Michelle walked to the door. Turned to me winked and gave me the five minutes sign.
Maybe after another cold beer, sweetie.
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FetishThe next night, Emma and Brent knocked on our door at 6 pm. Bruiser stayed next door at Emma’s, sleeping on her couch. Jess had decided that we pull no punches. We were both completely naked as we answered the door. Jess was wearing the nipples clamps (that she had originally bought for me.) They dangled from the erect nubs sticking out from her chest; I had played with her tits for several minutes before installing the clamps to ensure that they were rock hard. I, myself, wore nothing...
“Whatever you like, Mistress,” Jess said obediently. Emma pushed herself up to a sitting position; she then twisted her body to dig back in the pile of toys. Retrieving one, she turned back to Jess. “I want to fuck you,” Emma said simply, holding up a strap-on dildo which dangled in front of Jess’ face. “As you wish, Mistress. I’ll need a bit of help getting back up, though,” she said. She floundered a bit on the floor to show her lack of mobility. Emma leaned over and helped pull Jess back...
Once outside, she realized that he had driven and she had no way home. She took her phone back out of the clutch purse she had brought and discovered that her hands were still shaking in anger. Emma closed her eyes and counted backward from ten to calm herself. Reaching zero, she reopened her eyes and dialed Jess on her phone. “Hello?” Jess said on the other end of the receiver. “H-Hi, Jess. It’s Emma.” Emma’s voice was quivering while she hovered on the line in between ‘blind fury’ and...
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Back on dry land, the group found that I had laid out four towels on the sand over near the fire pit. I was aware of the schedule of events and was doing my assigned tasks. Jess and Amelia both dropped down onto towels. Andre and Paul sat down on either side of Amelia; Jess had to pull the other two boys down next to her by their hands. All of the guys had shrunken as a result of the cold water (no sympathy here), so Amelia wrapped her hands around the guys’ cocks and started pumping. Andre...
Emma knocked on our door that night at around 9 pm. She had just gotten out of work. She was smiling, but Jess could tell something was off as soon as she opened the door. “Hi, what’s up, Em?” she asked. I was sitting on the couch reading a magazine. Fully clothed for a change. I know that doesn’t happen much in these stories, but I actually do wear clothes every once in a while in real life. “Hey guys, it’s not too late to stop by, is it?” she asked. I could see her eyes looked a bit...
I am not used to getting tears, either sad or happy, after pleasing women and I was a bit flummoxed as for what to do; I decided to sit there on my heels looking stupidly at her nude body. Jess handled it much better by pulling Emma tightly against her chest. Jess coddled her head and shushed her softly as Emma cried hard against her. The tears made huge dark spots on Jess’ red blouse. “It’s ok, it’s ok...” Jess repeated in whispers. I gave Jess a questioning look and she waved at me to be...
I had to waddle my way back to the car through the mall thanks to the toy wedged in my bottom. As is typical for mall shoppers though, no one even gave me a second glance. I’m not sure they would have had I been naked from the waist down with the toy sticking out from me. “How much do I owe you for everything, Jess?” Emma asked. “Nothing, it’s our treat,” Jess said. “Really, I want to pa-” Emma started to say but Jess cut her off. “It’s not up for discussion. They are all gifts. I know...
Emma saw my erection hanging below me and noticed it was leaking pre-cum. “Jess, he hasn’t orgasmed yet...” It sounded more like a question than a statement. “No, he usually won’t from just anal. Even though he enjoys it, he still needs stimulation down there to push him over the edge,” Jess commented. “Should I stroke him or something?” Emma asked. “Yes, please!” I said eagerly before realizing my mistake. “No.” Jess said it very firmly. “For speaking without permission, he can stay...
A few minutes later, Jess returned to her own apartment. Emma was still seated on the couch, but she was clearly much calmer. “How you doing in here, kiddo?” Jess asked. Emma sniffled and nodded. “Better, I think, thank you. Was he...” “He’s still there,” Jess reassured her. “And I explained a little of what happened; I didn’t give him specifics. You can do that later if you choose. But he is very understanding. And very HOT by the way, good job!” Emma forced a giggle. “Thanks.” “Anyway,...
Before Emma could ask what she meant, Jess’ hands moved down to Emma’s crotch. Emma shivered at Jess’ touch as her fingertips tickled her sides on the way. Jess’ experienced digits had no trouble finding Emma’s clit, swollen from the excitement of screwing me. Emma settled back down onto me as Jess worked her magic. Emma’s eyes closed and she rested her head against the crook of my neck. I could feel her breath there as she sighed heavily. Emma rocked her hips back and forth against my lap...
The girls returned and stood above me as I moaned, eyes closed, lying on the ground beneath them... “Guess he liked it,” Jess commented, looking down on me with her hands on her hips. “Seems so,” Amelia agreed. She bent over and helped me up off the sand. She brushed off my back and I returned the favor for her. “K, children,” Jess said. “I think it’s time to call it a night.” The guys all helped carry the cooler and other gear back to the limo. Phil saw the mostly naked and covered in...
Jess and I (Pt. 2) By Sarah M. I followed Jess into the bathroom. "What the hell do you mean I have to start right now? I have my own life to live, remember? How can I just disappear?" "Sam, everything has been arranged. The principal has agreed to let you go to school as a girl, and as far as being a trainer for the football team; they already said they could get along fine without you. Don't worry about people making fun of you. Denise has already let the word out that...
Jess is a girl Jess is my name They try to tell me I'm a boy all the time But today something changed it aint hard to define Now they know Jess is a girl, and was all the time I was watching girls with my eyes I was envying their bodies, couldn't hold it I was praying to God every single night But now they know Jess is a girl they know Jess is a girl finally came out as a woman - like that Got tired of the charade finally knew it was time to change used to...
Emma’s bachelorette party followed a few weeks later. Jess and Emma had planned it together the day after the bachelor party. Jess had hoped to arrange it sooner but she wanted it to be after Emma’s twenty-first birthday. “K, so we need to put together a guest list,” Jess said, notepad and pen resting on her leg. Emma shrugged. “Um, you? And I guess Liz?” It was more of a question than a statement. Jess scribbled on the pad. “Sure. Anyone else?” Jess asked. Emma was quiet for a moment...
Jess took me by the hand and turned to Emma. She crooked her finger at her in a “Come here” gesture and led us both back to the living room. Without saying anything, Jess began unbuttoning my pants. Emma’s eyes went wide. “I, I ... don’t think I am ready for-” Jess interrupted her. “Calm down. You’re not doing anything. You are just going to watch. Have a seat,” she said, pointing to the floor. My pants were down on the floor and my underwear stuck out in front of me. Emma had already...
Back out on the floor of the store, Jess headed over to the ‘intimate apparel’ section. ‘Intimate’ in this case basically just meant bras and panties. I felt uncomfortable hanging around the area, like people would think that I was some sort of pervert (which I was. Am. Nevermind.) Jess picked up a few pairs of panties. The first was pure white and very lacy, completely unlike the boy-shorts that Emma was currently wearing. The second pair was a thong. “Jess!” Emma hissed. “I can’t wear...
Emma made it to PetHub with only seconds to spare; she had to hurry to make it to the time clock on time. Not that her boss was a bastard about that sort of thing; she simply took great pride in her work ethic and tried very hard to be punctual. Nothing exciting happened until she checked her phone while on break. “Holy fuck,” she said aloud in the empty break-room. Jess had forwarded a link to Todd’s page. Jess had added a note: “Hmm, guess he pissed SOMEONE off.” When she followed the...
“Ok, Slave Jess, Slave Aaron,” Emma said, saving Brent from having to respond, “I think this has been enough fun for one night. Brent and I should probably leave you two alone.” “As you wish, Mistress,” Jess said. I repeated the phrase a beat later. Jess knelt down in front of Brent. “Thank you, Master Brent, for playing with this slave’s ass, mouth, and pussy tonight. I hope you will do so again in the future,” she said to him. She wasn’t going to let him off the hook and she got Brent to...
My name is Will and I'm an average guy, not much to me. Slightly built at the age of 16 with black hair and a 7" dick. One day after returning from school with my sister Jess, we discovered a note saying that mom was staying with her sick sister to help out with her son and daughter. She'd left some money for pizza on the fridge in case we were hungry. Now at this point I should probably tell you something about my sister. She's 16 like me with blonde hair and fairly muscled from her...
I breathed a massive sigh of relief that I wasn’t to be the center of attention. “Yes, Mistress! Right away!” I said, running straight to the bathroom to get our gear. It took me a few minutes to fill the enema bag with the necessary warm water and gather up everything that would be needed. When I returned, I saw that Jess was kneeling on the towel, her face to the floor. I pulled a rubber glove onto my hand. I squirted some lube onto the enema nozzle and worked my gloved hand over...
Michelle and Akeema’s Dark Journey Part 1By Shabbadew2002Contact me @ [email protected]:This story starts off slow, but keep reading. If you enjoy the sexual humiliation of women you will get off on this tale. It might also be described as ?politically incorrect?. It features the sexual abuse and degradation of black women. The ?N? word, and other offensive racial terms are used. This, in no way, reflects the values of the author who, in reality, disapproves of such language. This...
How Michelle and I first met and lost our virginity to each other at the age of 15 and Fell in Love This story takes place in September of 1986: My name is Rob and this is my story hope everyone likes it. I met Michelle in the 10th grade as we both were in the same home room and had a lot of the same classes.At first Michelle and I did not get a long to well as she was very out going and popular for being a freshman .It was because she was very beautiful.She has long...