Special Delivery

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My true enfemme adventure with the pizza guy.
1.5k words
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Another story that actually happened to me. It's a bit long but I think it's worth it, enjoy.

I was 22 and had just moved into my first place by myself a few months before. It was so liberating having my own space to be my true self without distractions or interruptions. Every day I came home I immediately transformed into Amanda and loved the freedom she gave. Beautiful clothes, sexy makeup, and the shoes; oh my god the shoes. What else could a girl ask for?

Although I had had a few boyfriends by this time I was still pretty shy as Amanda and inexperienced as a girl. Every time there was a knock at the door I did my best to hide and pretend I wasn't home. I know it sounds silly but living in a very big conservative city I was terrified about being found out so Amanda just stayed home with the drapes closed. But little by little, every day Amanda was home, I became more comfortable as the woman I was.

One night after I had finished my nails I was feeling especially horny (and a little tipsy) I went to the computer and started to browse. After a little while I found a few videos of girls trolling delivery guys, you know the story: Girl orders some food, the delivery guy shows up, she "accidentally" flashes a tit, cocks come out of pants, etc, etc.

When I started watching some of them I thought "I wish I could do something like that." The thought of being exposed like that scared me but scared me in a very good way. After a few more glasses of wine I really started to think about it "you're passable, they wouldn't even try to stick around if you did this, you could always just close the door if things got weird." The more and more I thought about it the braver I became. By the time I had finished off what was left of the bottle it was settled...I'm going to do it.

I walked into my bedroom, opened my closet and started to put an outfit together. I had a beautiful, knee length, see-through, black robe; a a sexy black push up bustier with pink laces up the sides (made my natural A-cup breasts look like B's with a little help); black bikini panties; black, backseam, thigh-high stockings; and a pair of shiny black, 5", knee high gogo boots.

Once I was dressed up I went to put on my make-up. *Side note "ladies" do the make-up first and not with half a bottle of wine in you* After a few very unsuccessful attempts I finally finished my dark smokey eyes which made my eyes pop in just the right way and put on some Fuchsia wet-look lip gloss. I took a moment to look at myself in the mirror, took a deep breath, and turned off the light.

I went back to the computer and started looking for pizza places across town thinking that it would be better if it wasn't someone I might bump into at the mall the next day. I found one, picked up the phone, and called. When they answered I ordered, in the most feminine voice I could manage, a small pizza and a soda. When the guy said that I had to have an order over $15 for delivery I nearly screamed, but a few adjustments later I was told it would arrive in a little over half an hour since it was snowing outside and the roads were icy.

I had my cash ready and waiting at the top of the stairs, and waited for the longest 30 minutes of my life. I had decided to open up my living room drapes so that I could see when he pulled up and loved the fact that I wasn't hiding anymore. I opened another bottle and poured another glass of wine and slowly paced in front of my window, shaking with anticipation.

About 45 minutes later a car pulled up in front of my house and I saw an older man get out and start walking up my path. I ran to the bottom of the stairs, as best I could in boots, and reached the door just as he rang the bell. I took another deep breath and slowly opened the door.

He was around 40 years old and clean shaven. I peaked from behind the door and said "Sorry I left my money upstairs. Come in out of the wind while I get it" and started walking up. He said "Thank you" and I heard him open the door behind me.

I heard him clear his throat and say "Oh, sorry, I didn't." I said "It's alright, don't worry about it" thinking "yes, I did it!." I grabbed the cash and slowly walked back down the stirs. I saw him looking up at me the whole time with a puzzled look on his face. When I reached the door I took the pizza, handed him the cash and said "Here, keep the rest."

To my absolute devastation I heard him say back "Thanks buddy, um, Miss" and watched him quickly walk out. I was mortified. What did I do wrong? Was it my voice, was it my clothes, was something poking out, what? I resigned myself to thinking that it was ok, I did what I wanted to do, it's out of my system, and hey, food!

I walked back upstairs and went to close the drapes. When I got there I saw him standing in front of his car smoking a cigarette. He looked up at me for a moment, threw his cigarette in the snow, and started walking back towards my house. A few seconds later I heard the bell ring.

At this point I was panicking, what do I do? but I thought "it's ok, the door is closed, the latch is on." I walked back downstairs and asked through the door "Yes?" He replied "I just wanted to apologize, I didn't mean to say it like that I was just, you know."

I unlatched the door and opened it just enough to look. I told him "It's ok, I wasn't really thinking either. Sorry for making you see me like this" and started to close the door. I felt his boot bump on the door and he said "Can I see you again for a quick sec?" I didn't have much choice in the matter as I felt him slowly pushing back on the door.

I stepped back and stood there in front of him on the landing. He looked at me for a bit and very simply said "Nice." I didn't know what to say back so I just stood there and smiled at him. That's when I saw him reach down and start rubbing his bulge through his jeans.

At this point I was electric inside, this could actually turn into something. I looked at him and said "If you wanted I could help you out with that before you go?" All he did was nod and start taking off his boots. I walked back upstairs, looked over my shoulder at him and pointed towards my couch.

By the time he was upstairs I could see his cock outlined in his jeans. I asked him to have a sit and that I would be right back. I went to my room and grabbed a condom and a pack of lube. When I walked back in the living room he was already sitting with his pants at his feet. I told him I always play safe and he said "Whatever you want sweetie."

I got on my knees and rolled the condom over his dick. It was about 4-5" long and about 1.5" around, nothing to write home about but my god it was hard as a rock. I started slowly sucking him and after just a few minutes I could feel his balls swelling. He put his hands on my head and asked me "Can I fuck your ass?" I was only too happy to oblige.

I ripped open the package of lube putting some on my boipussy and the rest on his cock. I play at home with a butt plug so I'm usually ready to go anytime. I bent over the couch and felt him nestle up behind me. I felt his head poke through my hole, pull back out, then felt him start thrusting in and out slowly, all the way from tip to balls.

He must have been really close because I swear it was only a minute before I felt his cock pulse and my pussy get very warm. He pulled out and I could see the condom hanging off his cock full of cum. I offered to take it for him and pulled it off his dick. I walked over to the garbage and when I turned around he was already at the bottom of the stairs putting on his boots.

He just looked up at me, smiled, and walked out the door. I smiled and thought "What smells so good, oh yeah I ordered pizza."

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AnonymousAnonymous8 months ago

Wish I was the delivery gurl,and we both got a treat. I luv the name Amanda!

AnonymousAnonymousover 2 years ago

I thought you said " that it would be kinda long"?

AnonymousAnonymousabout 9 years ago

Wow so sexy would love to be brave enough

AnonymousAnonymousabout 9 years ago

good story. I dress, i am 46, not really passable but I do my best, and did similar. The guy who delivered the pizza was mid 50s, I had a short dress on, pantyhose, I thought it would be a younger guy, he smiled when he gave me the change, I said hold on, went to give him a tip and deliberately dropped the change. I bent over in front of him, stood up, gave him the change. He said you look very nice in that, I smiled, lifted my skirt and twirled, how nice, he looked at me, unzipped, he was semi hard, that nice. I pulled his arm toward me, closing the door. I grabbed his cock, stroking it, then led him to the bedroom, his hand was feeling my arse. I sat on the bed, sucked him slowly. He got hard, pulled back,i was excited, I grabbed the lube, applying it to the head of his cock, then turned and knelt, pulling my hose down. He didn't waste time, his cock finding my hole and pushing inside, holding my hips, fucking me, I was so excited I stroked my cock, my cum shooting out as I felt him pulse inside me, warming my insides. He didn't take long, he moved away, grabbed a couple of tissues and zipped up, hurriedly going out the door.First time like this, not going out and looking for someone. I enjoyed it, pizza and cock delivered to my door. Doesn't get better than that.

BrendaNWBrendaNWabout 9 years ago
I would order more take out

I would like to do that.. order out or delivery and give a nice tip.. I have answered the door many times nicely dressed but didn't flirt... they just acted professionally.. maybe should try..

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