Angela and I were both 22, in college, and she was by far the prettiest girl I'd ever dated. She was a little taller than me at 5'10", with long, straight black hair she tied in pigtails, and a pair of E cup tits she had no qualms about showing off. She was, as she liked to tease me, my 'big titty goth gf'. However, like all my previous girlfriends, she had not taken my virginity. I couldn't wholly blame her: i was extremely anxious about my size, and rarely if ever tried to instigate actual sex, though the few times I had she'd said she wasn't in the mood. In fact, I'd been a little surprised when she asked me out: she had a reputation as something of a size queen, and my own reputation as tragically underhung definitely preceded me.
Our sex life wasn't dead though: I gave her oral often, or used toys on her, and she sometimes reciprocated with hand jobs. When we began dating we agreed to an open relationship, but I'd asked not to be given any details about the guys she was seeing. I knew my insecurity issues would get the better of me. Whenever she said she had a date, I just pretended to myself it was with another woman. I still had yet to take advantage of our openness. I was, to be blunt, scared of girls, and died a little inside whenever I asked for a date. A 'yes' was almost worse than a 'no'. So many women had gotten me into the bedroom only to change their minds at the last minute. The good endings were situations like I had with Angela - girls who pretended my dick was just an ornament but let me pleasure them in other ways.
It perhaps said something about my self-esteem that I felt I was coming out ahead in this arrangement. Still at 22, with my 23rd birthday a few months away, I was starting to become self-conscious about more than just my size. It was embarrassing to still be a virgin at my age, and I felt like if I could just lose my v-card, I'd maybe gain the confidence to use my admittedly undersized member as well as possible and begin having a 'normal' sex life. So I asked Angela for a special birthday present.
A week or so later she told me to come join her on the bed. Before sitting down she shrugged her monochrome dress off her shoulders, so she was in nothing but her bra and panties, and told me to strip down to my underwear too. She undid the button on my boxers and let my stubby member poke out the front. Then she reached into the bedside draw and withdrew a toy - a hyper-realistic, dark brown dildo, with suction cup and balls. It was, she would inform me shortly, exactly 7.4" long.
She put her hand on my dick and stroked my hardening penis. "This is James" she explained "I'll leave it up to your imagination whether he's one of my current non-nesting partners or an ex. When he had to leave town for a month, he made this for me. It's an exact replica of his cock. Now, James isn't the smallest guy I ever fucked - I'd say I went maybe half an inch smaller on occasion - but he was below average for me." She held the dildo next to my own meagre member. It wasn't quite twice the size - I knew from obsessive measuring, that I was 4.3" in length - but it was close enough to be humbling. Doubly so when I knew this man was on the small side for her.
"I'm not a total size queen. This dick was plenty for me. Even the slightly smaller ones were enough. But this" she flicked the tip of my tiny dick meanly "isn't. So, no, I won't be fucking you for your birthday. That's called pity pussy, letting a guy fuck you just because you feel bad for him, and it's anti-feminist."
My face was bright red and my dick was embarrassingly, drippingly hard, but I just looked at my knees and said nothing.
"I have two rules about the guys I fuck. First, they have to be at least seven inches. Second" she paused and licked her lips for effect "they have to be black. There's a reason I started dating you, Jack. I knew from talking to your exes that you had a tiny dick and a fetish for BBC cuckold porn. So I honestly never expected you to ask me for sex. But when you did, I realised something. Stupid bitch that I am, I've fallen in love with you. So for you, and only you, and maybe only once, I would break one of my rules and fuck a whiteboy. But you are, still, far too small." She was edging my dick incredibly slowly and carefully, but I still nearly came when she said this "So... we have a few options. I did consider setting you up with a friend who does pity pussy, calling in a favour, even hiring a call girl, to fulfill your birthday fantasy. But then I realised: I rather like you being my babydicked virgin cuck. So if anyone's going to take your cherry, it
will