Hello,
This is a story about Sara who was my girlfriend during my late twenties. These events took place around 2010 or so.
Sara was a beautiful girl: super skinny, blonde, with perky breasts and puffy nipples. She was also a bit of an enigma sexually. She dressed sexy and knew how to flaunt her body and attract men. She watched porn and would masturbate too. But despite having many boyfriends in the past, she was still a virgin. She wasn't prude by any means. She had done nearly everything else sexually that a girl can do except actually having sex. In particular, she really enjoyed giving blowjobs. I think she grew accustomed to giving them to her boyfriends in high school and college in lew of having sex. But over the years as she gave more and more, she grew to love them and get incredibly turned on while giving them. Sara was the only girl I ever met who could orgasm without touching herself while sucking a dick. And though I'm sure every guy she was ever with wanted to fuck her, it's hard to complain with an unlimited supply of great blowjobs.
We met shortly after graduating college. We lived on the same floor of an apartment complex and met in the elevator one day. I helped Sara carry some boxes from the elevator to her apartment and somehow worked up the courage to ask her out for coffee. We hit if off after a few dates and quickly moved in together. Unfortunately, we had both signed year long leases so Sara still had to keep and pay for her apartment while living 95% of the time with me.
Sexually, the first few months with Sara were a complete thrill. I was getting weekly blowjobs after which I would go down on her until she came a few times. Eventually though, Sara brought up the elephant in the room that she was a virgin and didn't plan on having sex anytime soon. I told her many times that this was completely ok for me but it had apparently been an issue in her previous relationships and she wanted to get ahead of it. She asked if there was anything she could do short of sex to make me happy. I professed that her blowjobs were amazing and all I ever needed. Nevertheless, she remained skeptical and said all her previous boyfriends had told her the same thing.
This discussion went off and on for weeks. Despite my best efforts, Sara never truly believed me. Her discomfort really weighed on me and I eventually caved. Before I admitted my ultimate fantasy, I made her promise to not judge me and remember that I love her no matter what. Then with tremendous anxiety, I told her about my cuckolding fetish. She had heard about it before but was a little confused as I started to explain it. Basically, I told her that she was the most beautiful girl in the world to me and seeing her with another man would be like watching real life porn tailored specifically for me. She started to ask more questions and I was surprised by her general openness to the idea. I added that one of my previous girlfriends in college had cheated on me and hooked up with another guy at a party. I actually walked in on them making out while half dressed. I described that I was overwhelmingly jealous at the time but after thinking about it over the years, it became a kink that really turned me on. We both agreed that it was kind of messed up but she said that we can't change the things we like and that experience is part of who I am now. I also made clear that I had no intention or desire to be with any other women. I only wanted her. Or in this case I guess, I only wanted her but she would be hooking up with other guys.
Sara agreed to try out cuckolding but said she only wanted to dip her toes in the water at first. She wasn't ready to pick up a guy the next day. She wanted to do some research as well to make sure she would do a good job of it. She also said that she didn't want to be hooking up with multiple guys at the same time which meant that as long as we were trying out cuckolding, she wouldn't be hooking up with me. She added that this would prove my dedication to the fantasy. If I accepted any of her advances at any time, she warned that she would stop pursuing other men. I agreed to her stipulations with simultaneous excitement and trepidation.
The next evening Sara had devised a preliminary test for me. She put on a red, lacy lingerie top and thong (in the photo) that I had bought her as a valentine's day gift. She walked around the apartment in front of me as I watched TV and was obviously trying to entice me. I did my best to ignore her seduction but stole a few glances as she bent over to pick things up. Eventually, she sat on the coffee table in front of me, legs spread, and started rubbing herself. She said she was really horny and needed to suck my cock. I resisted but she kept pressing. She was really masturbating at this point and starting to moan. She said she'd do anything to taste my cum. I knew it was a test so I continued to hold out as she started pinching her nipples and biting her lip. I had a rock hard erection and would have probably cummed in less than 10 seconds in her mouth. She was really putting on a show. Finally she orgasmed and came back to her senses a bit. She congratulated me for not giving in and teased that maybe I would prefer she wear the lingerie for someone else instead. I laughed uncomfortably but she could tell that her jest was actually the truth.
Over the next couple weeks, there were several more tests. They all started with Sara trying to seduce me, eventually getting herself off, and then making a reference to being with another man. She had done more research too and her teasing was becoming more pointed. She mused about going to a club in a slutty outfit, dancing with strangers, and finding a guy with a bigger cock than mine to suck. Somehow I managed to make it through her gauntlet and she agreed to take her first cuckolding practice run in the wild. To my surprise, Sara already had a place in mind to try within walking distance from our apartment. There was a coffee shop in a small strip mall a couple blocks away that we'd walk to almost every weekend. In that same mall, there was a nail salon, a dry cleaners, a sandwich shop, and a boutique clothing store. Sara had her mind on the clothing store in particular. We had walked in there once together after she saw a dress she liked in the window. It wasn't a particularly nice store. I would describe most of their items as discount party/club outfits for girls. Anyways, when we went in previously, the clerk was this college guy named Paul who looked a bit like a football play. He was completely out of place in the female clothing store and he flirted with Sara a fair amount while we were in there. His parents owned the store apparently and he worked there on the weekends. We saw him a few more times since then when we were at the coffee shop. He would always say hi to Sara and smile before taking his coffee back to his store.
When we arrived at the clothing store, it was relatively late in the afternoon and Paul was just about to close up. Upon seeing Sara approach though, he quickly welcomed us in. He said we could shop as long as we want but he put the closed sign up on the window so no other customers would come in. Sara played a little coy at first and meandered through the racks of dresses while I followed behind her. Eventually, she found a little black wrap dress with a zipper all the way up the back. She picked it off the rack and asked Paul if we could try it on. Paul said yes and showed her a curtained area in the back of the store. Sara handed me her purse and went behind the curtain. After a minute or so, she said loud enough for Paul to hear that she didn't think she could wear this dress with a bra. A few seconds later, she snapped her bra off and handed it to me through the curtain. I was now just standing there with a purse in one hand and a lacy bra in the other. A minute of rustling later, Sara called out to Paul for help and opened the curtain. The dress covered her front but was only half zipped up in back. Paul walked over and she asked him to help with the zipper. She turned her back to Paul and he gently pulled the zipper up to the top. Sara then turned around and to my surprise the top of the dress was somewhat see through. It wasn't fully transparent but the rough outline of her breasts and nipples were clearly evident. Sara asked Paul if he liked the dress on her and he said yes without hesitation.
Sara looked at herself a bit more in the mirror knowing the pull she had on both me and Paul at that moment. She then turned back to Paul and said she was worried the dress might be too short. She sat down on a chair and explicitly asked Paul if he could see anything gesturing to her crotch area. She was wearing red panties and you could definitely see them the way she was sitting. Paul blushed as he looked and said it wasn't too bad but he could see her underwear a bit. Sara then got up, bent over, and asked Paul if he could see the outline of her thong through the dress. Again with slight embarrassment, Paul said yes. Sara sighed and said that she loved the dress but maybe she just couldn't wear it with any underwear. She then reached up under the dress, pulled down her panties, and handed them to me. Turning back to Paul, she did a spin and asked if it looked better now. Paul said it was perfect and she looked beautiful in it. To be honest, both Paul and I were in a bit of a stupor at this point with what Sara was doing but Paul did his best to keep up with her show.
Sara thanked Paul for his compliment and said she would like to get the dress. As they walked over to the counter, Sara told Paul that she planned to go dancing in the dress. She saw a small speaker at the counter and asked Paul if he could put on some music so she could take it for a test run. Paul obliged and turned on some generic R&B music. Sara looked at me, frowned, and said that I had my arms full. Turning back to Paul, she asked if he could take my place and dance with her a bit. Paul looked at me to ask if it was ok but Sara pulled him to her and told Paul to not worry about me. Paul was cautious at first but eventually let his guard down and started really dancing with her for real. After the first song ended, Sara turned around and he grabbed her hips and pulled her close. Shen then leaned down and arched her back as he grinded his cock into her butt. I had to sit down at this point because my erection was a very obvious tent in my pants. The second song ended and Sara and Paul separated finally. She told Paul that he was a very good dancer and would enjoy dancing with him again sometime.
There was a bit of an awkward pause at this point. Somewhat stupidly, I said to Sara that she should probably change back into her normal clothes before we go home. Sara jumped on the idea and agreed empathically. She joked that she'd look like a complete slut walking in this dress down the street. She then walked back into the curtain area and asked Paul if he could help her with the zipper again. Neither of them bothered to close the curtain as I sat feet away watching. Paul pulled the zipper down to her mid back and paused before Sara confirmed that she wanted him to pull it down all the way. As he continued to pull it down, the dress unfurled before completely dropping to the ground. Sara was now completely naked in front of Paul. She was in front of a three way mirror so every angle of her was visible.
Trying to keep cool, Sara turned around and thanked Paul for his help while touching his arm. There was another awkward silence but this time I couldn't think of anything to suggest. Both Paul and Sara stood there in front of each other for 10 seconds not saying anything. Eventually Sara came to her senses and started to apologize to Paul. She said that I had called her a tease many times and she had obviously just gotten Paul worked up with the dancing and her now nude body. Paul quickly replied that no apology was necessary but Sara insisted. She stepped towards him, kissed him on the cheek, and then on the mouth. He kissed her back and wrapped his arms around her. While they made out, Sara worked to unhook his belt and pants which soon fell to the floor. Sara then got on her knees, pulled down his boxers, and took his cock into her mouth. His cock was bigger than mine and Sara had a little trouble trying to deepthroat but was loving every second of it. Paul didn't notice but I could tell Sara orgasmed several times by her moaning. By her second orgasm, I came in my pants just lightly rubbing my cock against my leg. And after just a couple more minutes, Paul came too. Sara swallowed every drop of his cum and kept sucking him more slowly for another minute until he pulled out.
Paul stepped back and let Sara put herself together. He thanked her effusively for the blowjob and joked she was the best customer he ever had. He told her the dress was free of charge and she could come back anytime if she wanted to try on more. Sara thanked him too for his help and his amazing cock. She put the shirt and jeans on that she had worn into the store but I was still holding her panties and bra. She grabbed my hand and we exited the store together. As we walked back to our apartment, we were both giddy with excitement and horniness. I told Sara that her performance was perfect and more than I could ever dream for. Sara asked if I wanted to keep going down this path of cuckolding. I immediately said yes and even admitted that her show had made me spontaneously cum in my own pants. Sara didn't believe me until we got back into the apartment and I pulled down my pants and showed her. I hadn't cum for over two weeks at this point and had a huge mess all over the inside of my boxers. Sara laughed upon seeing the mess.
In the immediate aftermath of that first experience, Sara met with Paul many more times (sometimes with me observing and other times she just told me about it afterwards). Her unused apartment became a great venue for her hookups. One time after she had Paul over, she walked back to our shared apartment with his cum all over her face and let me masturbate while telling me every detail of the experience. She eventually started to tease that she wanted to lose her virginity to Paul. This drove me crazy and would make me cum on the spot anytime she mentioned it. I didn't know whether to take her seriously but it was thrilling regardless.
A few months later, Paul had to leave the area for a college semester abroad and Sara wanted to give him a big going away present. She told me I could be involved but I had to accept several ground rules. First, I had to be completely naked (I had never been nude before in front of Paul). Second, I would be tied up so I couldn't interfere or touch myself. Third, I would be blindfolded at the start until she decided to take it off me. And lastly, I couldn't back out once I was in her apartment and had to do anything she told me to do. I accepted her stipulations with a little bit of fear. I knew she had been reading a lot of cuckold erotica stories and probably stumbled upon some kinky ways to humiliate me.
We walked over to Sara's apartment later that evening in advance of Paul arriving. I stripped down and Sara used both novelty handcuffs and an assortment of ropes to tie my arms behind my back and my legs together. She situated me on my knees in the middle of her living room, put the blindfold on me, and told me to wait patiently. I could hear Sara changing clothes and getting ready as I waited in extreme anticipation completely naked. She then left the apartment without saying a word. I didn't know where she was going and my head was racing but I didn't move an inch. It felt like a couple hours until Sara came back but it was probably closer to a half hour in reality. I heard the front door open and close but no one who entered said a word. I was nearly shaking as I knelt there not knowing what was happening.
Footsteps approached me and then my blindfold was ripped off. I immediately saw Sara but Paul wasn't there. Sara was just wearing a robe. She asked if I knew what was going on but I said I had no idea. Sara then said I had two choices. Option 1: She would give me a blowjob but she would never tell me where she just was or what she did. Option 2: She would tell me where she was and what she did but wouldn't give me a blowjob ever again. She told me to wait and really think about what I wanted. After a moment of reflection, I chose option #2. She then grinned and opened her robe and explained that Paul had just fucked her on our bed and came inside her. She had lost her virginity and she loved it. I was shocked and incredibly turned on at the same time. I had a huge erection so I couldn't even pretend to be jealous or sad. She rubbed her pussy in front of me and came as his cum started to run down her legs. I was completely on edge the entire time. After teasing me and showing off the various positions they had sex in, Sara eventually untied me. She said I could jerk off while she watched but I only had 30s to cum. I started immediately. It's embarrassing to get a time limit like that but it's even more embarrassing to cum in less than half the time allotted. I came all over my stomach while Sara just watched and laughed. She had been counting down and only got to 17s when I came.
More stories to be told at a later date.
Nes - nesp33@gmail.com
