This story is 100% fictional and any resemblance to anyone living is entirely coincidental. This story contains explicit sexual descriptions. If you are too young or if the material is illegal in your area, please close the story now.
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This is the first story I wrote for publication at nifty.org. It's intended as a stand-alone story to get my feet wet before I publish longer stories. However, I may revisit the characters in the future.
Claire Introduces Me to New Pleasures (MF, anal, MMFF, bi) Written by TD Wood (t.d.wood.367@gmail.com)
Summary: Tyler and Claire take their first weekend trip as a couple. Claire introduces Tyler to her past as they expand their relationship with friends over the weekend.
Part 1: The Mountain Cabin (MF)
Claire and I decided to get away for a long weekend in the mountains of Pennsylvania. We found a small, isolated cabin in the mountains with a beautiful deck and a hot tub overlooking a fast-moving stream. There wasn't another house in sight! We had been dating for over six months; this would be our first time traveling.
We left after work on Thursday and got to the cabin around 8 pm. We were having a rough time at work lately, so I was happy to find there was no cell service in the area. I had warned my office that I would be unreachable so I was more than glad to have no bars for service! We already had some takeout on our way up so we grabbed our bags, and food and then entered the cabin.
We sat down at the only table for dinner and read through the materials left by the owner. It included a layout of the area showing that the nearest house was almost a half-mile away. The small cabin only included a single bedroom but a sizeable audio system, a large TV, and the hot tub on the deck. Luckily, the place had Internet access so we could connect our phones and our laptops, but I made sure the phone was being sent straight to voice mail for the weekend.
After dinner, I started cleaning up while Claire grabbed our bags and unpacked our few belongings in the bed and bathrooms. I had just finished cleaning up and putting our food and drinks away when Claire walked out of the bedroom without a stitch of clothing.
Claire is tall with an athletic build. She has long dark brown hair, blue eyes, and a never-ending smile. Her breasts were small but perky, and she had well-trimmed dark pubic hair.
"I'm going to relax in the hot tub, join me and grab edibles for us," She asked, walking past me and onto the deck. On our way here, we stopped at the last dispensary before crossing the border into Pennsylvania. Neither of us liked to smoke weed, but we enjoyed getting high on edibles from time to time now that they were legal back home.
I grabbed two edible gummies from the bag and headed to the door, dropping clothes as fast as possible.
Claire had already removed the top of the hot tub. The owner had left the tub on when they cleaned earlier in the day, so it was warm. All she had to do was turn on the jets and slide into the water. I stopped and watched her as she pulled her hair back and settled into one of the corner seats of the tub. She caught me watching her and simply gave me a huge inviting smile.
Once over by the hot tub, I walked behind her, pulled her head back, and kissed her deeply. After the kiss, I hand-fed her a gummy and ate one myself. The gummies were weak, but neither of us had much tolerance.
I sat next to her and enjoyed the water, the view of the mountains, and of course, Claire. We started talking, and Claire surprised me by talking about our future together. We were both successful in our careers and bringing down good salaries. She had just turned 30 a month earlier and I would be turning 30 in 6 months. She talked about buying a place like this in the future as a weekend getaway from our jobs, kids, family, etc. Things between us had been going great but this is the first time she had brought up the topic of a long future together.
Finally, Claire moved closer to me and sat on my lap, giving me a big hug and kiss. We had been in here for about an hour, and it was time to get out. We both desperately needed something to drink, plus the edibles were starting to take their desired effect. We got out of the hot tub and closed the top, I was about to follow her back into the cabin when she pointed over to a double-sized outdoor lounge chair and said, "Relax over there; I'll grab some water and be right back to join you."
I intently stared at Claire's bare ass as she walked back into the cabin while sitting around on the lounge chair. It was only a few moments, and she stepped back outside with two large glasses of ice water. My dick had been semi-erect since seeing Claire walk out to the hot tub. Her approaching me with a big smile, my dick became hard as a rock.
"Here, have a drink while I take care of that hard cock of yours." Clair handed me my glass, took a long sip, and positioned herself by my hard dick. She took it in her hands and then licked around the tip of the dick. Precum was starting to flow out, and she greedily licked up the fluid and even took the tip of her tongue and pushed it into my peehole. Claire's oral skills were the best I had ever experienced. I was in heaven.
Claire took her time at the head of my dick, keeping me as hard as a rock. Without warning, she then took my entire dick into my mouth. It was warm and wet and she knew how to keep the pressure around the whole shaft. A few times up and down on my dick, I was ready to cum. "Not so fast," she said, abruptly moving off my dick and letting it fall back onto my body. She stared straight into my eyes with a little smirk while licking her lips slowly. I couldn't take it and started cumming without anything touching my dick. The best part of cumming this way would be the ability to cum again in just a few minutes! Claire loves to tease me and bring me right to the edge, and like this, sometimes I get too excited and cum anyway.
"I can't let this all go to waste!" Claire bent back over and started licking up all the cum off my body.
After watching her finish up, including taking my still hard dick into her mouth again, I asked, "Let's move inside or grab some towels."
"There were large ones on the bed," Claire replied, "Why don't you go in and grab them?"
I got up, went inside, grabbed two large beach towels from the bed, and didn't waste any time. Claire was lying back on the lounge chair with her hands behind her head.
"Nice view!" She said, smiling as I walked outside with the towels and still no clothes.
"Stand up for a moment so I can get a towel under you." I asked Claire. She got up and I covered the chairs with the towels. The outdoor cushions were not the most comfortable against the skin.
Claire then laid down and spread her legs, exposing her dripping wet pussy. Clair kept her pubic hair closely trimmed and removed the hair right around her vagina, giving me a great view of the clear juices dripping down onto her pucked ass.
I got down onto the lounge chair and positioned myself between her legs. I started kissing her between her thighs, slowly making my way up to her pussy. I was breathing in her sweet aroma and finally close enough to push my tongue deep into her vagina. She tasted sweet, and I could hear a soft moan as my tongue explored deep inside her. I then replaced my tongue with two fingers and moved my tongue to her clit. I found the upper corner of the clit and made a deliberate motion knowing I would bring her to orgasm quickly. I focused on her clit while moving my fingers slowly inside her soft spongy G spot.
Claire was moaning and getting close to orgasm. I was paying close attention, so I knew exactly when her orgasm started. At that point, I put more pressure on her G spot and slowed down the movement on her clit with my tongue. I had tried this before and was able to bring her to multiple orgasms. I could tell I was having some of the same success again. Claire's orgasm started. 10, 20, 30 seconds, and she didn't stop. It seemed like minutes went by as the wave of pleasure flowed through her body. Eventually, she reached down, grabbed my head, and pulled me up to kiss me.
"Oh my god, I've never had anyone do that to me before. I love you so much." She said before kissing me and pushing her tongue into my mouth. I was sure she could taste her juices in my mouth and face.
After a few minutes of making out, Claire stopped and said, "I need you to fuck me now." The backs of the lounge chairs were still up, so Claire flipped over, got up on her knees, and pulled my dick towards her pussy. I didn't need a hint and kneeled behind her and pushed my dick into her pussy. She groaned as I entered her and started thrusting in and out. It wasn't long before I was cumming again, this time into her warm vagina.
I moved away as Claire flipped back onto her back and laid back. She had moved between her legs and right to the clit, "Sorry, I was so close to another orgasm."
I told her, "Don't worry, I can help," and dove between her legs again, replaced her hand with my finger on her clit, and pushed my tongue back into her vagina. I could taste my cum mixed in with her pussy juices. It only took a minute, and she had another quick orgasm.
Part 2: A Quiz (MF)
Late that evening, Claire and I were lying in bed with the TV on. We weren't watching, but she was cuddled in my arms, and we were browsing through our phones. It was probably around midnight, and I was about to turn everything off when Claire said, "Here is a fun quiz we should take."
I laughed, "Not another one of these?" Claire loved all these online quizzes, and recently, she's been talking about all these so-called relationship quizzes. "You know they are simply trying to collect your information!"
"This one is different. We both take the quiz, and then the results of our combined answers are emailed to both of us."
I relented, "OK, send me the link."
I opened the link. It was a sexual compatibility and kink quiz. Each of us would take the quiz independently and the results would be emailed to us. "Are you up for this?" I asked Claire.
"I am, are you?" Claire replied, looking back down at her phone and starting to answer the questions.
The questions covered all areas of sex and sexuality, from the very vanilla to the extreme. You had to answer if you had done this in the past and if you would be interested in doing this in the future. Claire was the most experienced and kinky woman I had ever dated, so there were quite a few "interested in tying in the future" types of answers on my part. It took about 15 minutes to answer all the questions. Claire was a minute or two behind. After she selected "submit," I checked my email. A few moments later, an email arrived with the results.
Claire and I read through the results. I was surprised. There were many items that I put as "interested in trying" that were showing up. I was starting to feel a bit self-conscious starting to think about how many of these things Claire had done in the past.
Claire and I talked for hours. She wanted to do this quiz so it would open up a discussion about our past and future together. She told me that she loved me more than she had ever loved someone in the past and wanted me to know about her history. One area that caught my eye was the questions about multiple partners and bisexuality. When I was much younger, I had experience with one of the other boys in my neighborhood exchanging hand jobs and blow jobs. I was curious about trying it again.
Claire admitted that her "Friends with Benefits" were sometimes multiple friends, and she enjoyed group sex. She was also more than satisfied with our relationship. However, I've been intrigued with group sex for years and continued to ask her more about her experiences. Eventually, we got into an earnest discussion about including another couple in our lovemaking. She was getting excited talking and thinking about expanding our relationship to include group sex.
Eventually, I turned off the lights and TV, and Claire cuddled up in my left arm. My right hand could reach around and work its way between her legs. I found her pussy and wet vagina. I ran a finger inside her vagina for some lubrication, then moved to start a steady motion with my fingertip against her clit. She spread her legs, giving me better access, and kissed me. She didn't stop kissing me as I kept the steady motion against her clit. Eventually, she came again with another shuddering orgasm.
After she came, I pulled her closer and we fell asleep.
Part 3: Brunch (MF, anal)
I woke up the following day to the smell of breakfast being prepared in the kitchen. It was almost 11 am, and I slept soundly through the night.
I got out of bed, still completely naked, and walked through the main room to the kitchen area. Claire wore an apron with nothing underneath, making eggs and bacon for breakfast. Her ass was completely exposed as I walked up behind her, hugged her, and kissed her on the cheek. My dick started to get hard as I pushed it against the crack of her ass.
"Let me finish this, then we can have a quick fuck before breakfast." Claire told me.
I didn't stop, moving one hand to her breast and another between her legs. Another minute or two and the breakfast was done. Claire turned the stove off and moved the eggs and bacon over. "I want you in my ass," Claire said softly, standing up and moving away from the stove. I didn't allow her to turn around but pushed her against the kitchen counter. There was a small job of coconut oil on the counter, so I reached over, quickly got the top off, and grabbed some oil with my fingers. Claire enjoyed anal sex could cum quickly if done right.
I took the oil and rubbed it around my now erect dick. I then took the remaining oil and worked my fingers around her ass. She was entirely over the counter, reached around, and pulled her ass cheeks apart, exposing her asshole. I worked my pointer finger slowly into her ass as she relaxed her muscles. After she relaxed, I slowly pushed a second finger into her ass, making sure she was loose and relaxed. Finally, I took my other hand, reached around, and started to rub her pussy.
"I'm ready," she purred.
While starting to rub her clit, I used my other hand to line my oiled dick up with her asshole. I then carefully pushed my dick into her ass. I took my time making sure her ass opened up. My dick wasn't that big, so she was taking my dick without any resistance. Once fully in, I paused before thrusting in and out of her ass. I took my free hand and reached around a grabbed her breast. She then moved herself a bit more upright and pushed her ass back into me. I knew this was her way of saying she was ready.
Claire was the first girlfriend that I had that truly loved anal sex. I thrust my dick slowly in and out of her ass while fingering her clit and massaging her breasts. Her ass enveloped my dick as I slowly moved it in and out. I knew I wouldn't last too long in her ass, but I also knew this would get Claire off quickly.
After about 2 minutes of slow thrusting and increasing moans from both of us when she said, "Oh god, I'm cumming!" I sped up my thrusting just a bit and started cumming a moment later.
"Don't move!" she said as I started to pull my dick out of her ass. "I love to feel it get soft inside of me then slowly fall out." I obeyed her and hugged her closer and kissed her neck. Eventually, my dick slipped out. A significant drop of cum mixed with coconut oil hit the floor.
Claire giggled, "Boy, did that feel good. Let me clean up quickly so we can have breakfast." Claire took the apron off, hung it in the kitchen, and made a beeline to the bathroom. I grabbed a paper towel and wiped myself off, cleaning up the floor. The kitchen smelled like a mix of breakfast and sex.
I made up two dishes for breakfast and brought them over to the table as Claire walked back in, still naked and beautiful as ever. We sat at the table and had a very late breakfast.
"So, are you still interested in group sex?" Claire asked while eating.
"Yeah, I always wanted to try it, but I would have no idea how to set it up or even how it all works," I replied.
"Well, lucky for you, I can help with both. I have two old friends in the area, well technically they were 'friends with benefits.' They live approximately 45 minutes from here. I invited them to visit us for the evening. I figured we could try this tonight and then have time to talk on Saturday and Sunday."
I laughed uncomfortably, "Why do I suddenly get the feeling that you had this planned?"
Claire looked at me, "I had my hopes, but I only called John and Tina when I got up this morning. They were more than happy to drive out here to join us for the evening. They know it's your first time so they will call to confirm before they leave and won't be disappointed if you don't feel comfortable with this now or even after they get here."
I finished my brunch and asked about the arrangements for tonight. Claire explained that they would be over around 6 pm and would be bringing dinner from a local pizza shop and some wine. She suggested that we shower and clean up breakfast then talk about the ground rules on the deck.
Part 4: John and Tina (MMFF, bi, anal)
Claire and I put some light clothes on for the first time since arriving and sat on the deck on the lounge chairs. She cuddled up next to me as we looked out over the mountains. Not long after 6 pm, we could hear, then quickly see a car driving up nearby. Claire and I had plenty of time to talk during the afternoon and lay out the ground rules for tonight. I was allowed to stop anything at any time, and John and Tina would not be pushing me into anything I was uncomfortable doing tonight.
Their car pulled up. Claire walked over to greet them. Tina got out of the vehicle giving Claire a big hug and kiss. John got out the other side of the card, walked around, and threw his arms around Claire and Tina, hugging them both simultaneously.
Neither of them looked anything like I expected. Tina was about the same height as Claire -- about 5ft 9" -- but blonde with a bit more weight. I wouldn't say she was chubby, but not the fit physique that Claire possessed. John, on the other hand, was about 6 ft 2 in, overweight and balding. I wouldn't call him fat, but he was way beyond a "dad bod," as Claire had mentioned earlier.
I walked over to greet both of them. Claire said, "John and Tina, this is my boyfriend Tyler." I reached out to shake their hands, but John pulled me in for a bear hug and then pulled Tina over to join in the embrace.
"Man, you must be something special for this woman to talk like she does about you!" Tina said as all four of us were now in an embrace.
Claire interrupted, "Let's go inside and have some dinner. Can I help you bring something inside?"
I grabbed a pizza while Claire picked up a bag of takeout, while John grabbed a small box with bottles of wine. "I wasn't sure what type of wine to get, so I got a mix." John said walking in.
Tina opened the door and held it open for the rest of us. The table was set for the 4 of us, so we laid out the dinner, opened the wine, and started talking, laughing, and swapping stories. The conversation continued for about 90 minutes when Claire stood up and topped off everyone's glass of wine. "Let's move outside to the hot tub." She said taking off her top and dropping her shorts to the floor.
Tina and John followed suit, quickly taking off their clothes and following Claire outside. Tina had blonde hair, and blue eyes and was slightly chubby. She had light skin with small breasts and pink nipples. I also noticed that she was shaved entirely, and all I could see between her legs was the start of a tight slit before it disappeared between her legs. Jon was taller than me and a bit overweight. He wasn't fat but much bigger than I was. However, when he dropped his shorts, his dick was huge. It had to be at least 6 inches flaccid, the longest dick I've ever seen outside of porn movies. Mine, on the other hand, was about half that size. The first thing that came to my mind was "great, I'm going to watch my girlfriend get fucked by a monster dick."
I got undressed and joined them in the hot tub. Claire saved me the seat between her and Tina while John sat on the other side. The talk quickly moved to sex. As we were talking, Tina reached her hand under the water and grabbed my dick. I was so nervous that it started to get hard, but I didn't get the instant erection that I usually do.
"Do you mind if I have some fun with Tyler?" Tina asked, looking at Claire and I.
"Of course," Claire asked as she looked over to me and asked, "Are you OK if I have fun with John?"
I nodded in agreement as Tina moved over and sat on my lap, grinding her ass onto my dick. Claire followed suit sitting on John's lap and grinding me like there was no tomorrow. I was watching Claire and John when Tina turned just enough to plant a kiss on my lips. I reached around and massaged her breasts.
The action in the hot tub was getting heated when Tina got up took my hand and said, "Let's go inside to the bed. Sex in hot tubs is not as great as everyone thinks."
I got up and followed Tina to the bedroom. Claire and John followed behind us.
Tina got onto the bed, leaned back, and made herself comfortable. She then made a 'come over here' sign with her hand and pointed straight down to her exposed pussy. I looked down and saw that Tina's legs were now spread apart. Other than her head, I didn't see a single hair on her body. Her labia were small and didn't even cover the open vagina I was now looking into.
I was about to dive in when Claire pulled me aside and said, "Ladies first!" Claire put her face between Tina's legs and started licking her pussy before focusing on her clit. I changed my focus, moved up to Tina's mouth and breasts, and went to work while perched on all fours. Tina was moaning as Clair, and I went to town on her. That's when I felt a hand on my dick. I looked over, and John had one hand on my dick and a second between Claire's legs.
Tina erupted into an orgasm. Claire looked up and saw John's hand on my dick. She reached over and grabbed his hand. "I want you to lay down on your back," she asked him.
He complied as Tina snuggled up against him. Claire started stoking John's dick until it was fully erect. Even though it didn't grow that much, it was still an impressive sight at just over 6 inches. Claire then straddled John and lowered her pussy onto his impressive dick. Once she impaled on his dick, he started moving up and down. She then looked over at me and reach out to pull me to her side. As she rode John's dick, she whispered to me. "I'm going to let him slip out, and I want to see you take his cock into your mouth."
I know Claire and I had discussed this earlier, but it was now going to happen. Claire then raised herself and let John's dick slip entirely out of her pussy. "Your turn, dear." She then said aloud.
I reached out and took John's dick in my hand. I slowly moved over so my mouth was less than an inch from the head. I could smell Claire's pussy juices, then finally took his dick into my mouth, tasting her juices on his dick. I started giving John a blow job while Tina was cuddling him. Claire reached over for the lube on the nightstand next to the bed.
I continued for a few minutes until Claire interrupted me. "It's time for the two of you to fuck me." Claire was working lube over he pussy and into her ass then handed the bottle over to me. She then got back into position and slowly sat back onto John's dick. Once she was down, she looked back at me and said, "Now I want you in my ass."
I took the lube, making my dick slick, and lined it up against her asshole. I slowly worked my way in taking breaks and letting her adjust to the intrusion. Finally, I had worked my way into her ass. Slowly John and I started thrusting. He thrust in while I pulled out, getting into a steady rhythm. I could feel John's dick moving in Claire's vagina as I thrust slowly in and out of her ass.
Claire was going crazy, moaning and saying, "Oh my god, yes, keep on going!"
I came but did my best to continue thrusting until I heard Claire yell, "I'm cumming" I pulled out and let John take a few more thrusts until he was cumming.
We all fell back on the king-sized bed and caught our breath. Claire wrapped one of her arms around me, cuddled up, and asked me, "Did you enjoy yourself tonight?"
I looked straight into her eyes and said, "I love you and want to share many new things with you."