She Hooked up with lots of People!
My girlfriend's name is Sienna. We're both in our late 20s. We were introduced to each other by a mutual friend and clicked immediately. We shared a lot of mutual interests and felt completely comfortable with each other right from the start. And just a couple months after meeting, we moved in together.
From the beginning, we decided to have an open relationship. Sienna had been in a couple open relationships previously and wanted the freedom to have fun occasionally without me. I didn't push back because I felt lucky just to be with Sienna in the first place. I also perhaps overestimated how successful I could be seducing other girls when Sienna was away. Over our first several months living together, Sienna hooked up with four other men and I hooked up with just one other girl. Our basic rules were that we had to be honest about upfront about anyone we hooked up with, we had to stop if we ever found ourselves developing feelings for someone else, and we always had to use a condom (even with each other). Though I dreaded it at first, I found myself looking forward to Sienna's hook up stories more and more over time. There was a tinge of jealousy but it was superseded by my intense arousal for her sexual proclivities and genuine happiness for her experiences of pleasure.
The open relationship didn't negatively affect our daily sex lives when we were together either. Sienna was practically a nudist in our apartment and rarely wore more than a pair of panties and a t-shirt without a bra. And she was nearly free use with me. I could approach her, kiss her, grope her, and initiate sex at any moment and she accepted it willingly and enthusiastically. She would also initiate sex on her own and give me regular hand jobs and blowjobs without any reciprocation. I had more sex with Sienna than I ever had before in my life. It was honestly incredible and just reinforced my acceptance of our open relationship ever further.
Unfortunately, neither of us had great jobs and we started running low on rent money. We really loved the apartment though and didn't want to give it up. It was a two bedroom apartment so we decided we should rent out the second room to help manage our finances better. We put some ads online and got a a few responses from younger people like us who were also struggling to get by on their own. We invited each of them to come over to see the place. The first potential renter was a guy who had recently graduated from college. He was a bit nerdy and said that he spent most days playing video games which we didn't love. The second was a girl about our same age. She quickly became uncomfortable though after we mentioned that we were in a relationship. The third candidate ending up being the best. His name was Shawn and he was a couple years younger than us. He had no problems with our relationship and seemed very chill overall. He was also quite fit which I could tell attracted Sienna. After talking it over, we decided to offer the second bedroom to Shawn and he moved in the following week.
Sienna tried to dress normally in the apartment after the Shawn moved in but that didn't last long. We ended up spending a lot of time together with Shawn in the evenings watching TV together and eating dinner and we grew increasingly comfortable with each other. One night, Sienna admitted to Shawn that she typically liked to be more relaxed with her clothing at home and asked if he would be ok if she wore a bit less in our apartment. Unsurprisingly, Shawn had no concerns and encouraged her to dress however she wanted around him. Sienna was pleased and immediately returned to her previous panties and t-shirt wardrobe. Shawn tried his best not to stare but I caught him eyeing her occasionally. I couldn't really blame him though as I did the same thing regularly.
About a month after Shawn moved in, Sienna was going on a short weekend trip to a resort with her friends. As she prepared, she inadvertently mentioned that I should wish her luck in finding a hot guy at the resort in front of Shawn. We were both a bit embarrassed but Sienna explained to Shawn that we were in an open relationship and we both semi-regularly hooked up with other people. Shawn said that was cool but admitted that he wouldn't have guessed that we were in an open relationship because we seemed so close to each other. Sienna teasingly asked him we couldn't be close while having an open relationship. Shawn just laughed and said he guessed it should be possible. He then cheekily wished her luck as she left and she thanked him while walking out the door.
While Sienna was gone, Shawn talked to me more about our open relationship. I gave him the basic details and was relatively frank about how it worked. He was pretty amazed to hear about it and repeatedly mentioned that he couldn't believe that I let Sienna hook up with other guys. I pushed back though and said that it was as dynamic that worked well for us and strengthened our relationship overall. A day later, Sienna sent me a brief text that just said "Success!". I knew that meant that she had found someone at the resort. Shawn saw that I was texting Sienna and asked what she had said. I thought I might initially lie but decided to just rip off the band aid and tell Shawn the truth. Living with us, he was going to encounter this reality eventually. I told Shawn that his luck paid off for Sienna and she had indeed found someone. Shawn was again amazed and asked if that meant that Sienna was fucking another guy right then. I said probably and he laughed. He asked if I was jealous and I said no. I told him that we've done this many times before and it always been positive in the end. Shawn pressed more though and asked "another guy's dick is inside your girlfriend and you're ok with it?" I said yes with confidence and I think he finally believed me.
Later that night before Sienna returned, Shawn asked if I would be ok if he hooked up with Sienna. I didn't know how to respond. I had never really contemplated that possibility though I guess I was naive to think that a handsome man in our apartment would be off limits to Sienna. I just said that it was Sienna's decision. Shawn seemed pleased and said he'd do it "respectfully, of course".
When Sienna came home, she told me about her weekend at the resort and her encounter with a waiter who she ended up giving her hotel room key. Her story was incredible as always and we had sex as soon as she finished telling me the details. Later as we laid together in bed, I told Sienna what Shawn had said about her. Sienna thought it was funny and mentioned that it was bound to happen sooner or later. I asked her what she was gonna do about it and she said she'd probably tease him a bit but she wasn't planning on hooking up with him. She asked if I'd enjoy that and I told her I would.
The following week, Sienna's outfits around Shawn became even more revealing. She wore a couple thongs that showed off her beautiful ass. And she spent some time around him in just a towel after getting out of the shower. She also talked to him more openly about her sexual experiences, including the one she had at the resort with the waiter. Shawn was enthralled by her stories and shared some of his own sexual experiences with her as well. I took it as just fun and games but didn't think it would lead anywhere too far. That was until Sienna asked Shawn if he fancied her though. Without a hint of embarrassment, he said yes. Sienna was impressed by his confidence and asked how he planned to go about it. I couldn't tell if she was still just teasing him or if she had other motives. Shawn explained that he felt an intense magnetism from her and it was inevitable for them to hook up while living in such close proximity. Then to my surprise, Sienna said they should do something about it then if it was inevitable. She then got on her knees in front of him and took off her shirt while he sat on the couch.
She was now topless and only wearing a thong. She reached up and pulled his sweatpants down and then his boxers. His cock sprang up in front of her and she grabbed it eagerly. This was the first time I had ever seen her actively with another guy so I was a bit shocked. She jerked him off for a bit before eventually licking the tip of his cock and then taking it into her mouth. I couldn't help but notice the size of his cock in comparison to me. He was at least two inches longer and noticeably thicker as well. Sienna's head started bobbing up and down vigorously and Shawn eventually stretched his hands down to grope her boobs while sucked him. Thankfully it didn't take long for Shawn to cum. Sienna took it all her mouth and continued to suck him for another half minute after he was finished to get every last drop. She then got up gingerly as if nothing had happened and said that hopefully that could hold him over for another couple days. Shawn laughed and said he'd try before getting up with a giant grin on his face and heading to his bedroom.
Back in our bedroom afterwards, I asked Sienna what happened. She just said that it felt right in the moment and she hoped it wasn't too awkward for me. I told her that it was amazing to watch but admitted that it had been a bit surprising in the moment. Instinctively, I went to kiss her but remembered too late that Shawn had just cum inside her mouth. Sienna returned my kiss strongly though and I faintly tasted his cum on her lips and tongue as we briefly made out. After breaking off our kiss, she told me that she was hornier than ever and we immediately proceeded to have sex on our bed.
Later that week, I had a late day at work. Not only was I stressed from the job but I also worried about what Sienna and Shawn might be doing together in the apartment without me. I texted Sienna, asked if she was ok, and asked if she wanted me to bring any food home. She replied saying she was just watching TV with Shawn and asked me to bring home some beers for them. I left work as quick as I could, picked up a 6 pack, and headed home. When I entered the apartment though, neither Sienna or Shawn were in the living room. Looking around, I quickly noticed that their clothes were on the floor in a trail leading to Shawn's bedroom. About ten minutes later, Sienna walked out of Shawn's bedroom completely naked and covered in sweat.
She said she didn't hear me come in but thanked me for getting the beers. She sat next to me at the table and opened a beer while still naked. Shawn then came into the living completely naked as well and holding a condom filled with cum. He threw on the table in front of us as if it was a trophy. He then sat down next to Sienna and grabbed a beer for himself. Once again, he had a giant grin across his face. I felt increasingly submissive around him, no doubt due to his escalating conquest of Sienna. We all finished our beers quickly and Shawn then picked up his clothes and went back to his bedroom. Sienna then picked up the condom full of Shawn's cum and headed into our bathroom. I followed picking up her clothes off the floor along the way.
In the bathroom, Sienna asked me to join her in the shower. I quickly undressed and got in behind her. She put the condom on a shelf of the shower alongside our shampoo bottles and soap. I watched as she put her head under the water and washed her body off with her eyes closed. I couldn't help but marvel at how beautiful she looked right at that moment. She then opened her eyes and leaned forward to kiss me. We started making out passionately under the water together. I eventually reached down to touch her pussy but Sienna recoiled slightly while apologizing. She said that she was quite sore from her session with Shawn and asked me to be gentle. I then got on my knees and started gently licking her pussy while she moaned softly. She eventually pulled back, grabbed the condom off the shelf, and dangled it in front of me with a devilish grin. She said that it was so hot last time when I kissed her after she had given Shawn a blowjob and he had cum in her mouth.
She asked if I wanted to taste his cum again. I was hesitant but she pleaded and promised she would make it up to me if I did it. I eventually complied and she proceeded to tip the open end of the condom towards me. I opened my mouth and Shawn's cum quickly slipped out of the condom. Sienna got most of it in my mouth but some spilled on my chin and around my lips.I initially gagged but kept it in my mouth as Sienna watched. She then told me to swallow which I did with a big gulp at once. "Doesn't it taste great" she asked. I just nodded. She the turned the condom inside out and washed the remnant of cum off under the shower head while I stood up. She then flipped the condom back around and started to put it on my penis. She explained that her pussy was too sore to fuck but she'd let me be the first to fuck her ass and take her anal virginity. I was thrilled but my excitement faded as we both noticed that Shawn's condom was quite large and loose around my cock. Sienna said it would still work and turned around while using some lotion to lube her asshole.
She bent over and spread her ass cheeks apart as I positioned my cock in front of her asshole. I started to try to insert my cock but she was incredibly tight and I was cautious not to hurt her. My cock kept slipping around her asshole and while I held the condom so it wouldn't slip off. She moaned seductively as I struggled to get inside of her and I unfortunately started to cum before even getting a half inch inside her ass. When Sienna turned around and noticed what happened, she laughed and said I would have better luck next time. She then slipped the condom off my cock and poured my cum down the drain.
Over the next few months, Sienna and Shawn had sex regularly. It happened almost every time they were together without me but they also did it an occasionally while I was home with them. Sienna behaved like a free use girlfriend for Shawn, just like she had been for me before Shawn moved in. Sienna gave me the lurid details occasionally about their hookups while teasing me with a handjob or blowjob. But as their sexual activities became more commonplace, that happened less and less. I realized at the end of one month that I hadn't had sex with Sienna at all for the entire month. She had only given me a couple handjobs and watched me masturbate a few times but she had fucked Shawn at least a dozen times. She also continued to use Shawn's cum as a way to tease and humiliate me. Anytime she gave Shawn a blowjob, she was sure to give me a kiss as soon as possible afterwards. And she took his cum filled condoms regularly. Sometimes she'd feed me his cum like she did in the shower. Other times she'd pour it on chest and make me lick it off. And a couple times she poured it on my face while laughing. She said that is was retribution for the many times I had given her facials in the past.
I also never got another chance to take Sienna's anal virginity. We talked about it a couple weeks after we initially tried in the shower and Sienna joked that she should take my cock first as a stepping stone before letting Shawn fuck her in the ass with his bigger dick. She asked if I wanted Shawn to fuck her in the ass and I shamefully admitted that I did. She laughed while promising that she'd save it for a special occasion.
Around this time, Sienna was investigating some alternative birth control options with her doctor and temporarily had a month gap in her birth control as she was switching to a new method. Sienna wasn't too worried because she always used a condom anyways. She told both Shawn and I about her doctor's appointment while we sat together on the couch. I was very accepting but Shawn was surprisingly turned on to hear the news. He asked Sienna if that meant she would ovulate that month. Sienna said probably but added that it probably wouldn't be full fertility like she might have when not taking birth control for an extended period of time. Shawn told her that he thought it was hot that she could get pregnant and Sienna blushed. That had never been a fetish of hers in particular but she was obviously intrigued by Shawn's interest in it. She told Shawn that she wasn't ready to stop using condoms but Shawn suggested that maybe he could just cum on the outside of her pussy.
That would be really low risk for getting her pregnant and she probably didn't have normal fertility anyways. Sienna asked Shawn what was in it for her. Shawn said it was just the thrill of the risk. He asked her if she had ever had unprotected sex ever but she admitted that she hadn't. He then said she was missing out because it can be really sexy. Sienna eventually gave in to his persistence and suggested that maybe they start with just a baby step before having full on sex without a condom. Shawn accepted her offer and asked her to stand up with him. He took his dick out and started jerking it in front of her. Sienna just laughed and asked him what he was thinking. He then pulled the top of her panties forward and asked her to hold them like that so he could cum in them. Sienna took off her top and then held her panties open just under his dick.
They kissed as Shawn continued to jerk himself and I just watched on the couch. And eventually after a couple minutes, Shawn started to cum, filling Sienna's panties and covering the outside of her pussy with his glaze. After he was finished, she let go of her panties which instantly pressed all his cum against her crotch. Sienna kissed Shawn again and then headed into our bedroom to clean herself off. I followed and found her in the bathroom looking down at the mess in her panties. I instinctively got on my knees in front of her and she pushed her panties down her legs. She leaned back against the sink and spread her legs slightly in front of me. I then started licking her cum covered pussy, attempting to both give her pleasure while simultaneously cleaning Shawn's cum off of her. She loved it and pulled my head tightly down into her crotch while she moaned. After cleaning off all the cum, I continued to lick her until she achieved an orgasm. She then stepped away from me while picking up her wet panties from the floor. She playfully threw them into my face as she got into the shower. I then jerked off and added my load to her panties while she remained in the shower and watched.
A few days later Shawn got horny again but Sienna was able to give him a blowjob to hold him off for a bit longer. But they discussed bare play further throughout the week and I could tell that Sienna was getting increasingly turned on by the idea. She told me that the chances of her getting pregnant were practically zero so she didn't think it was particular risky to try out Shawn's breeding fetish. She said she'd just do it once and then go back to using condoms all the time. I told her that it was her decision and she thanked me for understanding. I did feel jealousy that Shawn would do something sexually with Sienna that I had never done before. It definitely affected my confidence and I found myself both less capable of maintaining an erection and also more likely to cum very quickly.
My less frequent sexual interactions with Sienna didn't help either. I felt out of practice and when an opportunity did arise, I wasn't ready for the moment. It was a bit of a vicious circle too because I knew my performance issues only pushed Sienna closer Shawn for her own sexual gratification. The only orgasms I had given Sienna over a couple months had been with my mouth. And the times when I was most aroused were when Sienna included some aspect of Shawn's cum in our play. I was sure this convinced Sienna that I preferred to play after she had already played with Shawn and generally set her up to believe that pleasuring Shawn was a step in the process to pleasure me.
The following Saturday, Sienna and Shawn had nonchalantly planned to have unprotected for the first time. I wasn't sure if they'd do it alone in Shawn's bedroom or in our living room where I could watch. Sienna and I had lunch together at the mall that day and wandered into a lingerie store while walking around afterwards. I always loved shopping with Sienna but it was different now thinking that anything sexy that would be more for Shawn than for me. As we walked around, she admitted that she had been very horny for the past 24 hours in anticipation of her night with Shawn. She eventually found a lingerie set that she liked and tried it on in the dressing room while I waited outside. It was a very sexy red thong and bra but with semi see through fabric. It also had string ties on the sides so it could easily be untied and removed at a moment's notice.
She came out a couple minutes later and said she was gonna get it to wear tonight. We walked around the store some more and she also picked out a very short semi-sheer black robe. We then passed a sales rack of panties and Sienna asked if I wanted any. I asked if she meant for her but she clarified that she meant for me. I asked why and she explained that I seemed very into her panties after Shawn had cum in them and perhaps I would enjoy wearing some from time to time. I didn't know how to respond. Sienna said I didn't have to get anything but added that she thought it would be hot if I wore panties occasionally. She said it would be fun to play together while we were both wearing them. I was hesitant but eventually gave in to her cajoling. She held a few up against my waist to judge the sizing. A girl walked by while she was doing this and try to hide her laughter. She decided that a medium was the right size for me and then picked out a satin pink thong that she said was 'perfect'. She handed the thong along with the rest of her merchandise to me to hold while we waited in line at checkout. I then ended up paying for all of it and Sienna kissed me as thanks.
When we got back, Shawn was out with some friends so we had the apartment to ourselves. Sienna went into the bathroom and started getting ready for night with him. She took a shower, shaved, and had started putting on her makeup by the time Shawn got back. Sienna asked me to go out to the living room and explain that she will be ready soon. Shawn laughed at me telling him that and then just said ok. He told me that he'd be waiting for her in his bedroom. I went back to Sienna and told her what Shawn had said. She asked me to get the bag from the lingerie store and I brought it into the bathroom for her. She looked beautiful standing there naked in front of the bathroom mirror. She rarely did her makeup and hair but looked incredible whenever she did. I handed her the red bra and thong and she put it on. I was surprised how see through it was after she put it on.
You could clearly see every feature of her nipples and pussy. It left nothing to the imagination and was all in all a frivolous barrier to her body. The black robe made it a bit more modest but you could still see what she was wearing underneath. After she was finished getting dressed, she took the pink thong out of the bag and told me to put it on for her. I got undressed and then stepped into the thong before sliding it up my legs. The soft fabric felt incredible to be honest but I couldn't help but be embarrassed at the same time. My cock fit snugly in the front part of the thong but the back part sliding into my crack felt bit strange. Sienna was overjoyed though to see me wearing it. She even made me spin around so she could see it from every angle. She said I looked 'pretty' and asked me to keep them on until she came back. I promised her I would and then watched as she walked out the door and towards Shawn's bedroom.
Though I desperately wanted to see what they were doing, I stayed in our bedroom and waited as patiently as I could. I heard the occasional noise which was undoubtedly Sienna moaning in pleasure. After a half hour, I grew quite anxious. I wasn't hearing noises anymore but it took another fifteen minutes before I heard Shawn's door open and then Sienna returned to our room. She was completely naked, holding her lingerie in one hand and covering her vagina with the other. Her hair and makeup were a complete mess and she looked like she had been thoroughly fucked every which way by Shawn. She had a huge smile on her face though and said it was amazing. She threw her lingerie on the ground and pushed me onto my back on the bed. She then got on the bed and straddled over my face while still holding her hand over her pussy. She said she felt "so full" and added that Shawn hadn't cum in nearly a week. She asked if I wanted to see and I just nodded. She told me to 'open wide then' and I did.
She removed her hand and I could instantly see a bit of cum at the edge of her pussy. I stuck my tongue out and started to lick it. As I did though, a wave cum flowed out of Sienna's pussy. Learning from before, I swallowed as quickly as possible to avoid gagging. Sienna then pushed and a bit more cum came out of her, this time onto my lips and face. I kept licking her and she began slowly humping against my tongue. As she did, she said that her pussy was the sorest it had ever been and she walked nearly bowlegged out of Shawn's room after what he did to her. She continued to hump me my face while telling the details. First, he loved her lingerie but it came off very quickly. Then when she sucked him, she said she spent a lot of time on his balls. She explained to give the cum a good send off before it went on its journey through his cock and into her pussy. Shawn then carried her onto the bed and inserted his bare cock into her. Sienna said she could clearly tell the difference from a condom and that she liked it a lot better. "The friction was different" and "I could feel his warmth inside of me", she explained.
They went through every position you could think of before and Sienna orgasmed countless times before Shawn eventually got a pillow and put it under her butt while she was laying down on her back. He then lifted her legs back towards her head and so her pussy was sticking straight up towards him. Shawn told her the position would allow him to cum as deeply as possible inside of her and that gravity would help as well. He then stuck his cock back inside of her and fucked her slowly but forcefully. She said each thrust was the deepest sensation she had ever felt before. She also explained that she could more easily sense that his cock was tensing up without the condom and she knew he would cum soon. She was incredibly aroused was close to orgasming as well. Then when Shawn started to grunt, Sienna felt cum shoot inside of her for the first time. She said it felt incredible and she orgasmed just a few seconds after him. He leaned forward and they kissed for several minutes while he left his cock inside of her. Getting towards the end of her story, Sienna increased her pace grinding her pussy against my tongue and orgasmed once again. After she came to her senses, she teasingly asked if I had gotten all the cum out of her. I nodded and she then shifted down to straddle my waist.
I was lying there on the bed, wearing just a pink thong, and my face was covered in remnants of Shawn's cum. Sienna asked what she could do for me and it was hard to think of anything in particular on the spot after everything that had already happened. I eventually asked her to kiss me and we started making out. As we did, she humped her pussy against the erection inside of my thong. I was surprised how good it felt. And after a bit, I started to feel a mixture of her wetness and Shawn's cum flow through the thong and onto my dick. That sent me over the edge and I erupted in the thong while Sienna continued kissing me. She eventually noticed my erection soften though and asked what happened. I embarrassingly explained that I came but she barely believed. She then go off of my and looked down at my thong. She pulled up the front and then laughed. She said that I looked like her from a week ago after Shawn came in her panties. She rubbed the outside of a thong a bit and spread the cum thoroughly across my crotch. She then laid down next to me and cuddled me while saying she was exhausted. I laid motionless as she slowly fell to sleep and then I did as well.
The next morning, the thong was adhered to my skin from my cum the night before. I had to peel if off and through it into the hamper while Sienna watched and giggled. By the time we showered and got dressed, Shawn was already out in the living room. Sienna went straight to him and kissed him while telling him good morning. Shawn didn't even look at me and I could tell he had cemented his position in the hierarchy above me with Sienna. As Sienna left him to walk into the kitchen, he spanked her butt and she jumped and laughed playfully. Thought Sienna had originally planned on having unprotected sex with Shawn just that one time, her incredible experience doing it made her go back on that plan.
They continued to have regular sex and never used a condom (though Sienna still made me wear one when we tried). About a month later, Shawn also got to be the first guy to take Sienna in the ass. Sienna said it hurt at first but she really liked it after getting use to it. He even cummed inside her ass at the end and I got to eat that out of her as well. She bought me a few more pairs of panties which I wear whenever she asks. She even told Shawn that I wear them one night while they were hooking up. I felt completely humiliated by the entire situation but also wouldn't have done it any other way. I love Sienna now more than I ever did before.
Me & Sienna - mahmiss@tutanota.com
MORE CUCKOLD COUPLE POSTS
She had Sex with my Boss
Cuckolded by Former College Roomate
Exhibitionist becoming a Hotwife
