Notes to Young shemale with mature woman
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Not posted in a little while so thought might as well share an old experience I had with one of my fwb. This story happend while we were away on a holiday and needed sharing.
Its broken into 2 because we both wanted to share our experience. I read a story on here which was a little portion of the inspiration for what happened.
We flew out to Jamaica 10 months ago for our getaway and did the usual tourist thing. When we got horny for more then ourselves we took to the internet but astonishingly didn't get very far. We did how ever find a party to attend near our hotel and decided to go.
After a few hours we quickly decided it wasn't for us. There was too many d**gs for one thing and it didn't seem terrible hygene friendly. Despite our enjoyment of bareback fun we do have standards.
Luckily there was another couple there that seemed to be having a similar experience. I took it upon myself to start a conversation and suggested the 4 of us escaped.
We did just that and ended up having a lovely evening of a late dinner. The husband joe was a very friendly and funny guy and his wife Lana was equally as wonderful. They were both in their 60s and had been swinging since their 20s. They had hoped to be playing with a couple of similar age for various reasons, one being a bit of body envy/embarrassment. They both felt their best days were behind them. We did our best to convince them to not let that stuff get to them but they stuck to their guns. We all agreed to stay in touch as we had hit it off so well.
A few days later Lou received a message from Lana thanking us for a lovely evening and if we would be up for a repeat before we went home. We happily agreed and met them later that evening. Another lovely dinner and a few bottles of wine in Joe and I were alone and got onto the subject of their insecurities. It manifested after Lana watched him with a younger woman. She quickly became very aware of her age and how things in her words had drooped. I was a bit stunned as Lana had an amazing figure. And as if to compound the matter they were given some negative feedback from a younger couple they met via a swingers site.
I felt terrible for them. A bit later I explained this to Lou at the bar. She too felt so bad for them both as they are truly lovely human beings. "I've got an idea" she said.
We joined them again and Lou explained her plan. Our hotel room was a suite. It had a seperate bedroom and meant we could play seperated. Meaning Lana wouldn't have to watch Joe and get insecure. Meaning he wouldn't have to worry, they'd be relaxed etc etc.
They were obviously resistant. I convinced them to come back with us and at least have a nightcap.
In the hotel they began to relax. Joe was sat next to Lou happily and Lana seemed at ease. We ordered some champagne and put the music on. Lana and I got up and danced and I made a real point of keeping her tight to me. Drooping? Not a chance.
I looked over now and again to see Lou and Joe kissing. He had a hand on her leg half up her skirt and she was rubbing his crotch. Lou got up and our eyes caught. She started to lead Joe to the bedroom. She winked which was our pre approved signal. I whispered into Lanas ear that we were alone and I started kissing her neck.
She looked to see they had gone and I could see she was a bit tense.
"If you are uncomfortable say. We like you guys a lot" I reassured her.
"I'm fine." And we kissed. She tasted great. With that I peeled down her dress and kissed across her chest. This woman was so hot.
She sank to her knees and took out my cock. She ran her tongue over the length and took it in her mouth. Christ I nearly blew then.
She sucked me for a few minutes. Her skills incredible. I laybher back on to the sofa and hitched up her skirt and begam licking her pussy. It was bald and soaked and delicious. Lara held me head and bucked against my face as I brought her to orgasm. She stood and spun me onto the sofa and removed her skirt and top. Her boobs were larger then I thought and still pert. She wore a suspender belt with her stockings and it framed her perfectly. She straddled my cock and sank down onto me. We could hear Lou in the bedroom.
"You ok?" I asked still concerned for her. Lana kissed me and started moving her hips back and forth slowly.
"I'm fantastic." She arched her back and went for it.
- Rich and Lana were dancing. Why on earth did she think she wasn't hot was beyond me. Joe was casually stroking my leg and I turned his face and kissed him. I could feel his cock was solid under his trousers. I whispered into his ear. "Come with me." I stood up and looked to Rich. He saw me and understood. I led Joe to the bedroom and closed the door. He sat on the bed. I pulled my dress off over my head. I wored no panties or a bra, only my hold ups and heels, and he simply said "fuck". He quickly undid his belt and I helped him remove his trousers. I took his large cock in my mouth and he groaned. I worked his shaft and licked his balls being as attentive as I could.
"Get naked." I said and he jumped up. While he undressed I pushed the door open a bit to see the rest of the room. I could see Rich putting the moves on Lana and I laid on the bed so as to keep my view. Joe was licking my pussy and I was deliberately not quiet. His hands moved to my boobs now and then and he would occasionally slide fingers inside me.
He was very good. He got onto his knees and rubbed his cock on my pussy. I smiled and rubbed my boobs. He teased my hole then sank it in. I moaned and pinched on my nipples as he opened me up. He jad a fair amount of girth.
"Your pussy is amazing." I pulled him down to my face and kissed hjm again. "Check out Lana." I whispered. I turned his head so could see what I could see and we both watched. We could see the back of richs head and Lana sitting ontop of him riding away. Her hair was falling out and she gripped the back of the sofa.
"Want to join them?" I asked.
"Not yet." And with that he sat up on his knees lifted on of my legs and fucked me deep. I felt an orgasm surge upward and I groaned with pleasure. Joe was really good. Like stupid good. Not long later though he came. A huge flow of spunk shot all over me as far up as my chin. I thought shit thats that but he stayed semi hard. I licked his cummy cock and sucked him gently and soon I felt him twitch and stiffen. He was hard again got me on my hands and knees.
Round 2.
-Lana was amazing. I gripped her hips and she rode me like a horse. I could have stayed in that position all night. But she was definitely tiring. I took hold of her bum shuffled forward and stood up, still inside her. She held me round the shoulders and kept trying to fuck me. I walked her forward and lowered her onto the second sofa. Her hair was falling over her face and her cheeks were flushed. I continued to fuck her and she sucked on my fingers.
"Lana you are so fucking hot."
"You too." She panted. She really was hot too. I had to keep staring at the curtains to keep my load at bay. Lou was being wrecked in tbe bedroom judging by the noises and that wasn't helping my predicament. I felt it rising and Lana could tell. She pushed me back, got to the floor and knelt beneath my cock and wanked it hard. I shot my load all over her face and boobs. My breathing was ragged as she licked my helmet and sucked the last drops out. I sat back down with weak legs and she seductively wiggled on her hands and knees back to me and gently began to lick, kiss and suck me again. Nursing me back to life. I began to get hard again in time for the door to open
-I led Joe back to the main room. Firstly I needed a drink and secondly I wanted to play with Lana as well. We walked in to see her sucking Rich. She was dripping with cum and looked very satisfied. Joe sat down and remarked how good it was to see her relaxed. Even gave Rich a high five.
I grabbed the half empty champers and had a swig. Joe eyed me up and down as I casually walked back over to them all. I gave him the bottle and then moved to Lana. I seperated her legs and lay on my back between them. I pulled her freshly fucked pussy down and started to snake my tongue into it. She groaned on Richs cock. She stopped with Rich and turned to 69 with me. Joe sat next to us and fingered her and me in turn.
-The girls looked amazing together. I took a swig of champagne and took in the show for a moment. Lanas asshole kept winking at me so I got behind her and licked it. She sniggered and wiggled it playfully as I did. Lou swapped between sucking me and licking her. I had to have it. I nipped to the room and grabbed some lube and came back to prepare Lana. Lou had moved out from under her now and they both were playing with Joes cock. I went back to lana and applied the lube to us both. She looked back and fingered her owns ass as I lubed my dick. Being careful I slid into her and she groaned loudly. The sight of me fucking his wife in the ass was just want Joe needed and he suggested to Lou to do the same. She grabbed the lube and sat down onto his cock reverse cowgirl style. Her pussy was soaking and his cock filled her asshole perfectly.
We fucked the girls in the ass for good while. Though nature being what is it wasn't long before we both, almost simultaneously bucked and strained before dumping our respective loads. Mine all over Lanas perfect ass and Joe inside Lou. We were all spent. Lanas confidence restored she and Lou had casual play before we all decided sleep was better then sex.
2 days later they saw us both off from the Airport. We made truly great friends that night.
Its broken into 2 because we both wanted to share our experience. I read a story on here which was a little portion of the inspiration for what happened.
We flew out to Jamaica 10 months ago for our getaway and did the usual tourist thing. When we got horny for more then ourselves we took to the internet but astonishingly didn't get very far. We did how ever find a party to attend near our hotel and decided to go.
After a few hours we quickly decided it wasn't for us. There was too many d**gs for one thing and it didn't seem terrible hygene friendly. Despite our enjoyment of bareback fun we do have standards.
Luckily there was another couple there that seemed to be having a similar experience. I took it upon myself to start a conversation and suggested the 4 of us escaped.
We did just that and ended up having a lovely evening of a late dinner. The husband joe was a very friendly and funny guy and his wife Lana was equally as wonderful. They were both in their 60s and had been swinging since their 20s. They had hoped to be playing with a couple of similar age for various reasons, one being a bit of body envy/embarrassment. They both felt their best days were behind them. We did our best to convince them to not let that stuff get to them but they stuck to their guns. We all agreed to stay in touch as we had hit it off so well.
A few days later Lou received a message from Lana thanking us for a lovely evening and if we would be up for a repeat before we went home. We happily agreed and met them later that evening. Another lovely dinner and a few bottles of wine in Joe and I were alone and got onto the subject of their insecurities. It manifested after Lana watched him with a younger woman. She quickly became very aware of her age and how things in her words had drooped. I was a bit stunned as Lana had an amazing figure. And as if to compound the matter they were given some negative feedback from a younger couple they met via a swingers site.
I felt terrible for them. A bit later I explained this to Lou at the bar. She too felt so bad for them both as they are truly lovely human beings. "I've got an idea" she said.
We joined them again and Lou explained her plan. Our hotel room was a suite. It had a seperate bedroom and meant we could play seperated. Meaning Lana wouldn't have to watch Joe and get insecure. Meaning he wouldn't have to worry, they'd be relaxed etc etc.
They were obviously resistant. I convinced them to come back with us and at least have a nightcap.
In the hotel they began to relax. Joe was sat next to Lou happily and Lana seemed at ease. We ordered some champagne and put the music on. Lana and I got up and danced and I made a real point of keeping her tight to me. Drooping? Not a chance.
I looked over now and again to see Lou and Joe kissing. He had a hand on her leg half up her skirt and she was rubbing his crotch. Lou got up and our eyes caught. She started to lead Joe to the bedroom. She winked which was our pre approved signal. I whispered into Lanas ear that we were alone and I started kissing her neck.
She looked to see they had gone and I could see she was a bit tense.
"If you are uncomfortable say. We like you guys a lot" I reassured her.
"I'm fine." And we kissed. She tasted great. With that I peeled down her dress and kissed across her chest. This woman was so hot.
She sank to her knees and took out my cock. She ran her tongue over the length and took it in her mouth. Christ I nearly blew then.
She sucked me for a few minutes. Her skills incredible. I laybher back on to the sofa and hitched up her skirt and begam licking her pussy. It was bald and soaked and delicious. Lara held me head and bucked against my face as I brought her to orgasm. She stood and spun me onto the sofa and removed her skirt and top. Her boobs were larger then I thought and still pert. She wore a suspender belt with her stockings and it framed her perfectly. She straddled my cock and sank down onto me. We could hear Lou in the bedroom.
"You ok?" I asked still concerned for her. Lana kissed me and started moving her hips back and forth slowly.
"I'm fantastic." She arched her back and went for it.
- Rich and Lana were dancing. Why on earth did she think she wasn't hot was beyond me. Joe was casually stroking my leg and I turned his face and kissed him. I could feel his cock was solid under his trousers. I whispered into his ear. "Come with me." I stood up and looked to Rich. He saw me and understood. I led Joe to the bedroom and closed the door. He sat on the bed. I pulled my dress off over my head. I wored no panties or a bra, only my hold ups and heels, and he simply said "fuck". He quickly undid his belt and I helped him remove his trousers. I took his large cock in my mouth and he groaned. I worked his shaft and licked his balls being as attentive as I could.
"Get naked." I said and he jumped up. While he undressed I pushed the door open a bit to see the rest of the room. I could see Rich putting the moves on Lana and I laid on the bed so as to keep my view. Joe was licking my pussy and I was deliberately not quiet. His hands moved to my boobs now and then and he would occasionally slide fingers inside me.
He was very good. He got onto his knees and rubbed his cock on my pussy. I smiled and rubbed my boobs. He teased my hole then sank it in. I moaned and pinched on my nipples as he opened me up. He jad a fair amount of girth.
"Your pussy is amazing." I pulled him down to my face and kissed hjm again. "Check out Lana." I whispered. I turned his head so could see what I could see and we both watched. We could see the back of richs head and Lana sitting ontop of him riding away. Her hair was falling out and she gripped the back of the sofa.
"Want to join them?" I asked.
"Not yet." And with that he sat up on his knees lifted on of my legs and fucked me deep. I felt an orgasm surge upward and I groaned with pleasure. Joe was really good. Like stupid good. Not long later though he came. A huge flow of spunk shot all over me as far up as my chin. I thought shit thats that but he stayed semi hard. I licked his cummy cock and sucked him gently and soon I felt him twitch and stiffen. He was hard again got me on my hands and knees.
Round 2.
-Lana was amazing. I gripped her hips and she rode me like a horse. I could have stayed in that position all night. But she was definitely tiring. I took hold of her bum shuffled forward and stood up, still inside her. She held me round the shoulders and kept trying to fuck me. I walked her forward and lowered her onto the second sofa. Her hair was falling over her face and her cheeks were flushed. I continued to fuck her and she sucked on my fingers.
"Lana you are so fucking hot."
"You too." She panted. She really was hot too. I had to keep staring at the curtains to keep my load at bay. Lou was being wrecked in tbe bedroom judging by the noises and that wasn't helping my predicament. I felt it rising and Lana could tell. She pushed me back, got to the floor and knelt beneath my cock and wanked it hard. I shot my load all over her face and boobs. My breathing was ragged as she licked my helmet and sucked the last drops out. I sat back down with weak legs and she seductively wiggled on her hands and knees back to me and gently began to lick, kiss and suck me again. Nursing me back to life. I began to get hard again in time for the door to open
-I led Joe back to the main room. Firstly I needed a drink and secondly I wanted to play with Lana as well. We walked in to see her sucking Rich. She was dripping with cum and looked very satisfied. Joe sat down and remarked how good it was to see her relaxed. Even gave Rich a high five.
I grabbed the half empty champers and had a swig. Joe eyed me up and down as I casually walked back over to them all. I gave him the bottle and then moved to Lana. I seperated her legs and lay on my back between them. I pulled her freshly fucked pussy down and started to snake my tongue into it. She groaned on Richs cock. She stopped with Rich and turned to 69 with me. Joe sat next to us and fingered her and me in turn.
-The girls looked amazing together. I took a swig of champagne and took in the show for a moment. Lanas asshole kept winking at me so I got behind her and licked it. She sniggered and wiggled it playfully as I did. Lou swapped between sucking me and licking her. I had to have it. I nipped to the room and grabbed some lube and came back to prepare Lana. Lou had moved out from under her now and they both were playing with Joes cock. I went back to lana and applied the lube to us both. She looked back and fingered her owns ass as I lubed my dick. Being careful I slid into her and she groaned loudly. The sight of me fucking his wife in the ass was just want Joe needed and he suggested to Lou to do the same. She grabbed the lube and sat down onto his cock reverse cowgirl style. Her pussy was soaking and his cock filled her asshole perfectly.
We fucked the girls in the ass for good while. Though nature being what is it wasn't long before we both, almost simultaneously bucked and strained before dumping our respective loads. Mine all over Lanas perfect ass and Joe inside Lou. We were all spent. Lanas confidence restored she and Lou had casual play before we all decided sleep was better then sex.
2 days later they saw us both off from the Airport. We made truly great friends that night.
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