Size Mattered to Her: How I Became a Cuckold [m/f/m] | 2016

After I graduated from college, I worked in an office alongside a bunch of other recent college grads. All of us got along with one another and frequently went out drinking together after work. One girl, Sasha, and I hit it off really well and before long we were having a covert relationship at work.

Almost every day, we'd find a way to fool around behind our co-workers backs. Our frustration would grow throughout the day until I'd finally notice that the break room was empty. I'd walk by Sasha's desk and smile as I made my way, knowing that she'd follow. Once we were together, we'd only have a couple minutes to make out passionately and whisper sexy things into each others ears. One time, she was pouring herself a cup of water when I approached her from behind and wrapped my arms around her, whispering into her ear how badly I wanted to fuck her as I slid my hand down the front of her pants. Other times, I'd help her at her desk only to "accidentally" land my hand on her thigh instead of her chair's armrest, and explore underneath her skirt.

We began hanging out outside of work, and that's when we became involved sexually. We had known each other for a couple months and between the happy hour drinks, break room thrills, and phone calls, we had built a surfeit of foreplay. However, we actually never had sex, and the following story explains why.

One day when my roommates were gone, Sasha came over and we began making out before I even got the key in the door. I had been single for months and was ready to explode inside her, a girl that I found more beautiful than anyone I had ever met. On the other hand, Sasha had just gotten out of a long term relationship. She had been with her ex-boyfriend for close to five years with the relationship beginning in high school and lasting throughout college. Unfortunately for Sasha, her boyfriend decided he needed some space and accepted a job offer in another state, hurting her deeply in the process.

Back to the scene, we made our way into my bedroom where I laid her on my bed and got on top of her. I pinned her arms down and began kissing her face and neck. I wanted to taste every part of her. In fact, just kissing her was better than the majority of my sexual experiences I've had due to our lightning-in-a-bottle chemistry. After I slid her tank top straps down her arms and kissed her collarbones, she freed one of her hands and stuck it down my shorts. She began fondling my cock as I got hard. After a few moments her phone rang and rather than ignore it, she picked it up. Fucking her would have to wait as the moment was ruined.

Strangely, a couple weeks passed and Sasha became slightly more distant. We'd talk on the phone and have our little sexy moments in the break room, but we weren't hanging out outside of work. A few weeks later when the sexual energy between had built up so much that we couldn't take anymore, we hung out at my place again.

Sasha and I continued our passionate kisses, but this time she took control. While laying on the bed, she removed my pants and began stroking me. She had a slightly contemptuous look on her face, as if she was turned off but trying to hide it. I had never thought about the size of my dick until she started going on: "We could do anal with it. My ex always wanted to do anal but couldn't." I didn't know where she was going with this, but she wasn't making eye contact with me. Interestingly, we always made eye contact, especially when fooling around with one another. It aided our chemistry. She went on to crush me when she said in an unapologetic tone, "His was too big for it. He always wanted to try it, but I told him, 'Sorry, but you're too big'".

Shocked, I couldn't believe she was telling me about the size of her last boyfriend while holding my cock in her hand. In her eyes, I'd be good for anal sex but certainly not for vaginal. I was so shocked I didn't even try to defend myself. It became clear to me that Sasha preferred well endowed guys. I understand many women get demonized for this, but it's just a preference, similar to how some men prefer wide hips or Asian girls, etc. In retrospect, I've tried to remember why she would be so callous. Perhaps I brought up past relationships or something that hurt her, so she used the size card to attack me. She might have mentioned my size anyways.

Over the next few weeks we continued to see one another, yet she consistently brought up the size issue. "One of my boyfriends and I had great sex. He'd make me squirt as I could cum four or five times in one session. Funnily, he thought he was big, but he was actually quite small." Happy to know she was open to smaller guys, I asked her if he was bigger than me when she shrugged it off and said she couldn't remember.

Talking about her ex-boyfriend while we were in bed was becoming a ritual for us without my consent. We still hadn't fucked each other, even though I had gone down on her several times and made her cum with my tongue and fingers. She'd bring up her ex and how her first sexual experience with him involved another girl. She had gotten very jealous watching another girl blow him, so she decided to do whatever it took to get him. All the while, I sat there listening about how much she loved fucking him despite our lack of full on sex. I was deeply hurt by all of this and received no sexual pleasure from any of it. However, I'd soon learn that painful events can often turn into sexual excitement. I was developing a liking for erotic humiliation.

Things really began to take their toll at work. Sasha had clearly spread the word amongst co-workers that I was ill endowed. Only weeks previously, I had never thought about my size; now, I was being subjected to size related nicknames by multiple female co-workers. One girl, Rene, came up with the brilliant nickname "Smally" for me, which rhymes with my nickname everyone calls me, "Pauly".

I'd consistently ask her where she came up with it, but she'd just laugh and ignore me. Over time, other girls began saying it, sometimes with hurtful intentions. One time I was upset with a co-worker and told her in a harsh tone how to perform a simple job task. Her cold response was, "Whatever... Smally". She hit me where it hurts.

On another occasion, Sasha was standing nearby when a girl began calling me Smally. I was devastated as I watched Sasha crack up. A third girl joined in and said, "Smally McBally!" which caused Sasha to bend over in laughter. As immature as it was, it was really painful and similar to bullying. I remember confiding in a friend about it later that week.

Over time, I realized how much of a "size queen" Sasha was. She'd tell me that she liked small dicks and that she wasn't sure why "all these girls like 'em so big", only to berate me over my size later on. For a while, I thought we were meant for each other, only to find out my lack of size. Even though I'm on the small side of average, her ex boyfriend was almost double my size.

I stayed positive and researched as much as I could about pleasing women. I wanted to make it work. We continued to hook up from time to time, and I'd do my best to tease and make her extremely wet. I suggested bringing in toys to the bedroom, as I wasn't intimidated by a large vibrator. Rather, I'd do anything I could to make her happy. Plus, I got really turned on seeing her filled up. Furthermore, we were still getting along great and our chemistry was wonderful.

Yet one day Sasha ignored my text. Then she ignored another the next day. And the next. She finally responded, "I don't want to talk to you outside of work anymore." Shocked again, I was hurt. Later that night, I was horny and couldn't help but fantasize about her. She had the sexiest body with smooth, olive skin. I'd imagine her in her black cheeky panties walking around my room, teasing me with her little ass. As I got closer and closer to climax, I started fantasizing about her wearing those panties in front of her ex boyfriend. More than likely, she had worn those for him before going down on him. I recalled her stories of her sucking him off before getting fucked. Without thinking about it, I shot a violent eruption of cum all over myself while letting out an intense moan. Within moments, I hit rock bottom. Since I couldn't please the girl I loved, I jerked off thinking of her fucking her big dick ex boyfriend. Albeit painful at the time, my cuckold fetish was born.

Sasha and I maintained our formal relationship at the office over the next month. We were professional and only spoke about job related tasks. However, I still had confidence despite all I had gone through - from being called Smally to having Sasha go on about how big her ex was - and was single. Subsequently, I would flirt with other women. Eventually I built some chemistry with a co-worker. One evening, Sasha was within an ear shot when a girl and I made plans to meet up that night.

Jealousy got the best of Sasha and after the girl had left, Sasha was back to talking to me in an informal fashion. She told me she could've had me if she wanted. I could tell she was jealous. Our undeniable chemistry got the best of me, so I shot back, "Well why don't you have me tonight?" Foolishly, I blew off the single girl that I could've formed a healthy relationship with for a girl that was cuckolding the hell out of me.

Sasha came over that night, but this time, I felt like I was in the driver's seat. She had come crawling back to me. As a result, I laid down the law. I wanted to know why we weren't fucking and finally she admitted it was my size. She told me she was conflicted since we had great times together and she still found me attractive. She told me how jealous she was seeing me flirt with another girl and make plans with her. Then, she asked me how I'd feel if she was making plans with another guy right in front of me. At this point, I realized I had nothing to lose.

"I'd probably get excited."

I explained to her how I'd been masturbating to her every day since we stopped talking. Mainly, it was the thought of her fucking a well endowed guy that had always put me over the top. Plus, my new cuckold fetish was so exciting that sometimes I'd cum three or four times a day thinking about it. Although it was slightly masochistic in nature, I figured I'd roll with the punch and enjoy it rather than beat myself up over my size. In a way, I had turned a bad thing into a good thing. And at the end of the day, the majority of women don't care anyways.

She was intrigued as she asked me what my biggest fantasy was, "I want to see you get fucked by a well endowed guy. I want to see you in ecstasy in a way that I couldn't provide. I'd love to see you arch your back in pleasure and call out his name." I couldn't believe I had the guts to say this, but she actually looked excited. I know she liked the toys we were using but preferred the real thing. She smiled, began kissing me and told me we could work something out. It turns out that Sasha was a bit of an exhibitionist, as she told me her biggest fantasy was to be watched while having sex.

A couple weeks passed at work and our relationship was doing well. Our connection was still amazing, but now we knew where we truly stood. We were never going to be boyfriend and girlfriend. Consequently, we could really take it easy around each other and have fun. During one day in early April, Sasha mentioned her ex, David, was coming to visit her during spring break.

To my surprise, Sasha told me that they "had never officially broken up." I asked her if he'd be okay with letting me watch them have sex, which she promptly replied with, "No way." Luckily, I had a plan and Sasha was down with it.

There was a company party with everyone from work one night. Sasha showed up with David. She introduced me to him but I remained very formal, as if Sasha and I were co-workers and nothing more. I watched the two of them from afar throughout the night. Sasha sat on his lap and smiled and laughed at his every joke. She was wearing a slinky black dress with red lipstick, while he was wearing slacks and a collared shirt with a tie. I was jealous, but insanely turned on at the same time. I imagined that this was foreplay for them before fucking each other. I began getting hard and a pre-cum began to moisten my boxers when I imagined her little mouth fitting around the head of his dick.

Little did David know, Sasha and I had a plan to fulfill both of our fantasies. When Sasha and David made their rounds of good byes, I immediately left and went over to Sasha's place. Sasha lived in a studio apartment with a balcony about five or six feet off the ground. Intentionally, she left the back door unlocked, which allowed me crawl in to her apartment unnoticed. From there, I hid in her closet underneath a pile of her clothes with the door slightly open. Within ten minutes, Sasha and David were in the bedroom making out.

I remained perfectly still like a good voyeurist should. I was actually pretty comfortable as I sat down in the dark with clothes and other belongings draped around me. What's more, the only light in the room was provided by candles. Sasha undid his tie and began rubbing her hands across his chest. She looked so petite in comparison and I was getting extremely aroused as she wrapped her legs around him, causing her dress to fall around her waist. I was seeing her in a new light. She would never act that way with me.

Wasting no time with lengthy foreplay, her boyfriend pulled her dress off, leaving her in red lace boy shorts. It was hot, passionate sex. Her hands ran uncontrollably around his back and I knew she couldn't wait to finally have a deep, hard fuck. Her frustration was no more.

I sat in the closet extremely turned on, being able to see firsthand how a man truly pleasures a woman. For once, I'd hear Sasha moan, scream, and finally, get fucked. Quickly, she began exploring his waist with her little hands, until she undid his belt buckle and lowered his pants. He shook them off and stood in front of her, until lowering his briefs and letting his dick springboard out of his pants.

I'm pretty comfortable with my sexuality. I like women but I understand sexuality isn't back and white. He definitely put me in the gray area. My jaw actually dropped when I saw how perfect his dick was. It was almost as if Sasha had turned me into a size queen myself, despite the fact that I had no desire to sleep with a man.

Sasha moved to the edge of the bed and began jerking him off with both hands. She stroked him with such energy and vigor that she looked like a different person than the one who had been with me. She began to lick the underside of his shaft before giving little kisses and sucks to the head, leaving her red lipstick all over it. She wrapped her lips around the tip and I desperately wanted to cum, but knew I had to hold it.

When Sasha couldn't take it anymore, she leaned back and guided him in between her legs. He fucked hard and deep. Within a couple pumps she was moaning as if the neighbors' sleeping habits didn't matter. I couldn't believe how vocal she was. She was like a different person.

To my shock, she came in what felt like a minute. Maybe he could just hit the right spots, but she came quick. For me, it had taken lots of technique, foreplay, and oral to get her off. Don't get me wrong, he had technique and made her wet beforehand, but it was awe-inspiring to see how effortlessly he could please her during penetration.

Sasha had to slow down, but soon enough, she was ready for round two. And round three. And round four. I watched her get on top of him and fuck him. I watched her get on all fours as David wrapped his tie around her neck and proceeded to pound away. Finally, she got on her knees and sucked him off until he came all over her face. She was so obsequious to his every demand. It was the opposite of our sexual relationship where I had always focused so much on pleasing her. Instead, she was focused on pleasing him. Also, everything truly sunk in. I could finally see why she didn't want anything serious with me after being with him.

After she cleaned her face off, I watched as she adored him when they laid down on the bed. I saw her make surreptitious looks in my direction until she recommended they take a shower together, which was my cue to leave. I waited until I heard the shower turn on and began to slowly creep out. Sasha ran back into the bedroom naked. Funnily enough, this was the first time I had ever seen her completely nude. With me, she had always kept her panties on. Even when I ate her out she'd keep her underwear on, pulling them to the side to allow me access. Anyways, she hurriedly approached me and told me to slip out the back door. I gave her a kiss and thanked her for what was the sexiest moment I had ever experienced before she pushed me out.

Sasha and I remained friends, but we both quit the office within a couple months. She was going to grad school and I decided to move to another town. Whenever I'm horny and need release, I think of her fucking him and I get off within moments. I understand technique is more important than size and that size only matters to a certain extent, but her bitchy, degrading comments are the reason I've become such a cuckold.