Pimped Out Tomboy

You always seemed to rely on me to meet new people, my friends were your friends, and of course they were all dudes. Perhaps that’s how you ended up a tomboy. Even so far as having rumors go around that you were a lesbian. You were this tiny, almost boyish looking thing. Only after you finally grew your hair out a bit, accentuating your girly figure just enough, people stopped thinking you were my little brother when we went out in public.

We had always been best friends. It was only natural we started dating. We had always spent all our time hanging out together and easily caved to our curiosity. It just kinda happened naturally one day, all that really changed was that we were also having sex. In fact it took us a bit to finally get used to referring to one another as boyfriend & girlfriend. 

Despite your outwardly shy persona, you were a total freak. Not so much in the normal BDSM ways really, you more so loved the mental stuff. Tying your wrists behind your back was fine, but what made it really exciting was having them tied when the landlord showed up unannounced. I left you kneeling there in the living room, just barely out of sight from the front door while I talked to him.

After I came back, you were oddly insistent on when he was gonna be back to check, whatever the hell he wanted to check. The topic went on for a bit…“Was he coming back today or…”   It was surprising, especially after knowing each other for so long, that we ever learned anything new about each other. That day we learned just how many fucked up things we thought seemed hot.

So… we tried some stuff. When the landlord came back later the next day, wanting to check for a leak in our kitchen that might be affecting the downstairs neighbors. I let him in without hesitating. He walked inside and saw you on your knees, handcuffed, blindfolded, and topless. Your face was bright red from embarrassment, and so was his.

I didn’t even acknowledge the situation. I asked if he needed help to break his attention from just staring silently. He regained his composure, said he’d be fine, and went to work.

We didn’t really have anything planned, but this situation was such a rush I couldn’t help but lean into it. You were right there so I just walked up to you and stuck my dick in your mouth. The entire thing wasn’t just in his view, it was practically in his line of site. Whenever he’d look up he’d see your face getting fucked…  It wasn’t long until he determined the leak wasn’t from us and for a moment he just sat there waiting for a moment to interrupt. Once I noticed this I awkwardly asked if he was done already, forcing your face into my pelvis trying to quickly finish. You coughed and started to squirm a bit, only after I started to cum did I let go. As you pulled back several good ropes landed on you. Face, hair, tits, even some thankfully landing on your thigh and sparing the carpet. The landlord glanced over to you constantly on his way out.

We were hooked.

It also seemed we found the best way of getting around your anxiety. Just let me put you in these situations, and you’ll just ride it out. As long as you didn’t have to do any of the talking.

I put you in all kinds of crazy situations. From making you strip down in the park near us while we went for a walk, to making you come out into the living room naked when the guys were over to drink and play board games with us. “Who cares,” they’re our friends, doesn't matter if you hang out around them naked. That one took some pre-gaming on your part. Our friends were frequent witnesses to our antics…

One time we ordered a bunch of delivery while they were over, the order was placed as cash apparently, and none of us had enough cash on hand… so I whispered in your ear. Your face went red, but you didn’t hesitate. Kneeling down in front of the delivery guy still standing just outside our front door. Without anyone exchanging any words, the guys and I watched you give a complete stranger head. He only talked when he warned you he was about to cum. I told him to cum on your face… He did, and we ended up with free food.

That was both the most exciting thing and the scariest thing yet attempted, so naturally we took it a step further…