“What have you been measuring?” Tess asked me innocently.
My heart-felt like it skipped a long beat and my stomach felt like it suddenly dropped in terror. I tried to keep my face straight as I turned back around and saw her laid across the bed, her slim figure alluring even under her clothes.
In her hands she was examining a small plastic ruler, the kind you get in any stationary set, which I remembered using the previous night. I think I had got it as part of my student kit, purchased long before I started my university course. At some point, during my second year I had found it buried in a box and, suddenly curious, decided to measure my cock.
Tess was my long-term girlfriend, a slim and gorgeous woman who was also at my university. We had regular sex and although I was always aware that I was smaller than I had thought, she had always kept any comments to herself although I had caught the odd masked taunt every now and then which I ignored. While I was defensive over my smaller size, I did find it oddly exhilarating to imagine her with other men. Her dark red hair was splayed out on the pillows in my student room, fanned out where she had dropped herself after coming in, finished with work and deciding to stay over.
I went over and lay down on the bed next to her, my mind was racing desperately trying to think of an excuse.
“Oh, I was rooting through some old boxes and it must have fallen out.” I said, knowing how lame the lie sounded.
She cocked her eyebrow disbelievingly and I watched for a long moment as she studied the ruler silently. After a moment, I realised what she was doing. She was mentally measuring up my cock! We stayed silent for a moment and I was caught up in a rush of feelings I wasn’t quite sure about. Was I really turned on about her measuring my cock with a ruler?
There was something really alluring to finally confirming to her I was smaller than I was supposed to be. I suddenly wanted to make those fantasies of being cuckolded to be real and without really knowing why, I decided to see how far she would take it.
“Hey, what are you doing?” I said.
She turned to me and looked me in the eye and smiled sweetly. “Nothing”, she protested, then returned to looking at the ruler.
My heart started racing again and I felt my cock stiffen slightly in my jogging bottoms.
“Are you…measuring me up?!” I mock-exclaimed.
“Of course not!” Tess’ face flushed up immediately. Although she would sometimes tease me subtly about my size, she would never have expected me to challenge her on it.
I knew immediately that I wanted to try to push forwards with this. The disappointment which ripped through me was totally real and now those hot cuckold porn films I had become obsessed with seemed strangely within reach.
“It’s OK if you are”, I said.
“Really?” Tess frowned, unused to me being so open about it.
I nodded towards the ruler. “What do you rate me? Be honest.”
Tess seemed to be caught off-guard now. “Umm, I don’t really know.”
“Come on”, I encouraged her. I was definitely turned on now and I was caught a little breathless about where this could end up.
Tess shrugged again and went back to looking at the ruler.
“Well…” I said. “Do you know what the average is?”
“Umm, it’s about six inches, isn’t it?”
I felt a twinge of horror go through me at that. The ruler was a transparent plastic ruler just six inches long. When I had wanked myself off the previous night and measured myself, I didn’t fill up the entire thing.
“So what do you think I am?” I asked again, secretly enjoying how nervous she had become.
My cock was fully hard now, tenting up my bottoms which she would openly see if she looked down at me.
“I don’t know.” she said slowly. “Five and three-quarter inches?”
She was playing it safe but I felt such a rush of arousal knowing that she was being tactful, but openly admitting that she thought I was less than average.
I playfully prodded her. “Come on, be honest. I won’t get mad I promise.”
She hesitated for a moment and then asked cautiously. “OK… five inches.”
I was definitely turned on now. I felt like I would be able to cum without even touching my cock it felt so primed to explode. Just that moment, Tess also noticed my hard on.
“Oh my god, are you hard talking about this?” She exclaimed.
It was my turn to hesitate now. “Yeah, actually I am.”
Her mouth fell open and her gaze lingered on my tented trousers before flicking back to the ruler momentarily.
“Do you want to find out?” I asked, propping myself backward so I was resting against the headboard.
“What? Measure you?” She asked, frowning even heavier now.
“Yeah. Come on, it’ll be fun.”
She stayed where she was, a disbelieving laugh escaping her briefly. Suddenly she smiled.
“OK, but you did hear what I said right? Five inches.”
I nodded again. “I heard you, but I want you to find out for yourself. Be totally honest with me on what you think though, it’s actually a bit of a turn on hearing that you think I’m a little smaller than average.”
“You’re turned on by it?” She asked, her mouth opening wider. “Why?”
“I don’t know, but I am.”
She smiled again and sat up, shuffling on her knees across the bed until she was kneeling between my legs. She put down the ruler and tugged at my jogging bottoms until my cock popped out. It was rock hard and stuck out pathetically, I never felt myself so small as I was just then as she regarded it carefully.
“You know, I don’t think I’ve ever seen your cock out in open like this. You usually keep it hidden away. Are you sure about this?”
I nodded again, barely able to catch my breath enough to answer her.
“Well”, she said, tilting her head to the side as she looked at my hard cock. “I want to get an accurate measurement, so I’d better make sure it is totally hard.”
With that, she bent her head down and I was enveloped in an exquisite heat and moisture as she took my cock into her mouth. She never had any trouble taking the entire length of me into her mouth at once and I fought hard to keep my orgasm from taking over me.
Her head bobbed up and down, pleasuring me in a way I hadn’t really let her do before. Her tongue flicked over the end of my cock, teasing my in a way which crushed the rest of my breath out of my body.
Finally, she reared back and stoked my wet cock absently as she smiled up at me and lifted up the ruler. It was really was the point of no return but I was so horny it didn’t even really cross my mind to stop her as she pulled my cock upwards and slowly put a corner of the ruler against the base of my cock.
“Are you still sure?” She teased, slowly bringing the ruler up so it was straight along the side of my penis. “No going back… No more hiding your size from me.”
My cock felt as if it were getting even harder, I wondered if I might be so turned on it would be bigger. Somehow, I would look down and it would be pushing the length of the ruler and then some, I felt like the thing which felt so ready to explode between my legs couldn’t possibly be small.
I did look down, and I will never forget the excitement as I saw her smile to herself as she brought the ruler along the side of my cock. She frowned, confused for a moment and adjusted it, obviously thinking there had been some mistake.
I felt electrified at the touch of her fingers as she bent down and examined the ruler. Her eyes focused on the number and there was a moment where her smile faltered as she finally found out the true extent of my shame.
“Four inches?” She asked, disbelief written across her face. My cock twitched with excitement and she laughed out loud. “It’s only… FOUR INCHES!”
“Well, it’s a little over four,” I pointed out.
Tess stifled another cruel laugh. “Yeah, OK, four-and two-eighths inches. It’s… different to what I thought.”
My cock gave another strong jerk, I could feel my cum desperate to burst out of me. I was riding on waves of tantalising humiliation. I leant my head back and felt myself losing control.
“Do you like the fact I know how small your cock is now?” Tess asked me quietly, ever so slowly running her hand down the length of my cock and taunting me with every word. “You are very small, aren’t you. Does it make you really horny?”
I nodded, lost in this fantasy come true.
“I knew it wasn’t big. I thought you must’ve been ashamed of it, but it turns out it’s even smaller than I thought it was.”
She stopped stroking me, forcing me to look at her. She was smiling widely. “Do you like me teasing you about your little tiny dick?”
“Yes,” I replied quietly, knowing I was sealing my fate forever.
Tess frowned. “Yes, what?”
“Yes, I like being teased.”
“About what?” She asked mockingly.
“I like being teased about my little… tiny… dick.”
“Oh, that’s good sweetie,” Tess said, resuming her slow stroke to a groan from me. “Because I kind of like doing it.”
Tess continued to stroke me, examined my cock from every angle with a displeased expression. “No wonder I’ve never cum during sex, I have to really concentrate to feel your little thingy inside my pussy.”
“I’m going to cum,” I suddenly gasped.
“I know you are, sweetie. I hope you enjoy it because it’ll be the last time your tiny four-inch cock is going to cum for a long, long time. Only men get to cum, and you’re just a little boy. Aren’t you ashamed of having such a tiny cock? I bet you got teased about it all the time, didn’t you?”
She started wanking me faster and faster, her voice getting gritty with her dominance. I was completely under her control, totally and utterly swept away on my arousal.
“You know, there is a good thing about you having a little cock and finally letting me control it. My pussy is super tight, like a virgin because I’ve never been fucked by a real man, with a real long and thick cock. I’m going to give a real man so much pleasure with my tight little pussy, and you’re never going to feel it again with your tiny, little-willy.”
I thrust upwars, cum exploding out of my cock in thick streams. Tess made comforting noises, cooing my softly and slowly stroking out more and more of my sperm, coaxing it out of my with a smile. Cum splattered up my stomach and Tess reached up and rubbed it into my skin.
“Enjoy it, baby, enjoy this. You’re not going to get another for the rest of your life.”