"So I will see you at 8 next Saturday?" I asked hoping he doesn't back out.
"You got it!" Charles replied, we both hung up, I was excited.
We spoke on the phone for a couple hours getting to know each other a little more. He was 28, lived in his mom's basement, was a huge Star Trek fanatic and worked 2 jobs, one as the shoe department manager and the other at a book store in downtown. After his father passed away, he has been taking care of his mom and tried to help pay the house and other bills. He wouldn't go into great detail, but he did explain he hated labels, but he was attracted to anything that walks, except animals! He also let me know, he was nervous when he made the offer of shoes for a blowjob, but he couldn't help himself he needed some relief and I made it happen. He asked me what I was wearing, before I could get to myself, and I told him I was just laying on my bed wearing the shoes I got from him and a pair of panties, maybe it was me, but I think he was breathing a little too hard if you know what I mean.
I explained to him my experience with my friend (another story), and let him know, when I'm in boys clothes, I can't do anything with a guy, but if I have women's clothes on, I'm good to go (I learned that from my friend, when he tried to kiss me when I wasn't wearing any femme clothes) – I know weird but that's me .
Next Saturday was a little more than a week away, but I needed to think of what I was going to wear. I decided to take a shower, and as shaved my body, I started thinking I was going to need new undergarments, makeup, always wanted to wear thigh-hi stockings and maybe a new outfit. After work the next day, I went shopping at my usual store, of course I got the glare from the old lady at the cash register, but I'm getting dick, she isn't!
As the days went past, I was counting the days and the hours for our `date'. The Friday before D-Day, I re-shaved my body again lotion my legs, painted my toenails to the color of the fake fingernails (deep red). Got my backpack ready for the trip downtown, and went to bed early, wearing my panties to bed I figure would help me get in the flow of things, but all it did was make me horny, thinking of Charles rubbing his hands on my ass, and me rubbing his cock through his pants, as I was thinking of everything, I needed my own relief I slid my hand down my panties and started to play with myself, after a few moments, I came like I never came before, with the cum settling on my stomach, I swiped it off my fingers licking it clean, thinking of tomorrow night.
When Saturday arrived, I did my chores, my mom wanted to spend sometime with me, so I went to lunch with her thinking it would make the time go faster, it didn't. I think I checked and rechecked my bag to make sure I had everything. I took another shaving shower session, and it was time to get ready. After putting lotion on, I put my pink bra on (I really need something to fill these out with one day), matching pink panties, pink garter belt and the white stockings (I really should have worn them more than just once in that weeks period, I keep forgetting how tough they can be to put on). I looked in the mirror, not bad at all, I thought to myself. I decided to wear a faded blue denim skirt that button up the side and a black tank top, and a blue buttoned shirt, this way I can hide the bra straps when I take the bus back and forth, and it was time to cover my feet and legs. Grabbing the backpack, I left the house to grab the bus; luckily it was late at night so not too many people were heading to the downtown area. I sat close to the back where I hid myself, as I rummaged through the pack finding my fake nails; one by one I put them on sometime reattaching if it didn't look right or when I accidentally knocked them off rummaging for something else. I finally was there nervous as all hell, but there.
"Hey cutie!" I heard from behind, it was Charles, we hugged but nothing more.
"So where do you want to do?" I asked, wanting to kiss him, but definitely not in public.
"Since the movie theater is right here, let's see a movie!"
Once inside, it wasn't that big maybe 2 or 3 theaters, we get inside our theater just as the previews started, through the light from the film, looks like there isn't but maybe 2 or 3 people and they look old! We grab the seats at the back, I excused myself and went to the men's restroom, thank goodness, it wasn't too far away from the theater, but it was still scary. I went into the stall, stopping and listening for anyone to come in, I undressed, leaving my socks for last, I stuffed my boy clothes into the backpack, undid my button down shirt and tied it upfront, took the lip-gloss out and stuck it in my skirt pocket. And pretty much ran out of there just so that no one saw me. When I open the theater doors, I stayed in the little hallway, took my socks off and slid the heels on, and walked up to the back of the theater. He looked entranced into the movie as I sat next to him. That didn't last, as I leaned over and gave him a kiss on the lips.
"I was wondering why it took you so long, which restroom did you use?"
"Men's room, I pretty much ran out there." I whispered back, we were laughing
"Shhh!" someone hissed.
"Guess we better be quiet!" I remarked he held my hand to quiet me down a little, and we started to make out. Feeling his tongue inside my mouth was hot, but feeling his hands going up and down my thighs was magnificent! We stopped for a moment, to see why every one screamed, have to love horror movies. His hand were firmly planted on my thigh, my hand was slowly tracing the outline of his cock through his pants. When the scene passed, he undid his zipper and I grabbed it as quick as I could. Lord almighty his cock felt good in my hands, the heat he generated, the feel of his smooth head I wanted that cock in my mouth more than anything else, but there wasn't much room for us to really have fun, occasionally he would stand up, acting like he needed to go to the restroom, and put his cock against my lips, and I would readily accept the invitation, opening my mouth sucking on the head, then he would sit down again. We stopped what we were doing so we didn't get thrown out, but it didn't mean the teasing wouldn't continue. He would play with my stockings and my thigh; I was still rubbing his bulge. As the movie was preparing to end, I told him I was going to change again, and he whispered "Don't! I want to walk with you dressed like that; I have a place we can go to!"
When everyone left I grabbed my bag, and walked out shaking like a leaf, I never done anything like this before. Luckily with it being dark, nobody noticed me. We held hands, just joking around about different things, it felt great to be out feeling the summer breeze on my stocking legs, having the moon see a different side of me. We made it down to a gay bar and grill, obviously they didn't care too much about who entered. He sat me down at a booth and ordered a beer for me and him, and burgers to eat. This was way too cool, looking around guys were drinking with guys, one corner is a make out session it was great to see people just be themselves. On the TV, was a baseball game, funny hearing the guys talk about sports in a sexual way. There were a couple of other guys in drag, how could I tell, their legs were hairy...gross! Then something hit me!
"Hey Charles, have a question if I needed to use the restroom where do I go?"
The poor guy almost spit his beer out laughing, "Around here I don't think it really matters, besides the 2 guys in drag, have you noticed any women?"
"Guess not, excuse me while I go!" gave him a quick peck and walked to the room.
Walking to the women's restroom couple of people are looking at me, but I'm thinking more because I was young than anything else. I get into the stall, I started to hear something, once I'm done I reapply my makeup, and curiosity took over, I walk to the other stall and was astonished to see a guy buttfuck another. The guy receiving looked like he was ecstasy; I tried to be quiet leaving as they were enjoying themselves. I made a dash once I left the restroom to the table.
"Dude! This guy is getting it up the ass in the bathroom!" I was trying to whisper
"And? Did you enjoy what you saw?" almost mad that I said anything
"It wasn't bad; the guys look like they were having fun. But it's a public bathroom!!!" pleading for him to understand.
"And what exactly were you and I doing in the theater? Have you ever had anal sex?"
"Understood, no I never had anal."
"Well, if it is ok with you, I would like to pop your anal cherry, but not until your ready! Cool?"
"Cool!" the thought of his cock in my ass sounded great, then I thought about the pain, I always read in those porn magazines, but that guy in the stall didn't look like he was in pain. "Ready to go?" Charles was getting up, finishing his last bit of beer.
"Where are we going now?"
"C'mon! You'll see!"
Again we walked, darker than before same direction.
There on building XXX' movies...we headed inside the building. He paid for him and I to see the movie, taking my hand Charles led me to the back with the cashier reminded him, No sex in the theater!' loudly.
The room was dark and the air conditioning must have been set to 0, it was freezing. We stood against the wall. There was a smell to the theater, when I got my most of my eyesight back, I could see the men in the chairs, Charles took my hand and led me to a smaller room. There everything came to focus, there was a guy getting tag teamed by two guys, another `girl' like me who was the focus of a bunch of guys.
"Stand in front of me!" Charles whispered. "Just watch the fun, way better than the movies!"
He was right, the guy getting double teamed, just got a face full of cum. The girl was standing up and getting ready for a near naked guy to give to her in the ass. She was pretty, slim wearing a black dress and extremely high heels, her makeup was a mess from the cum of a previous donor, but that didn't stop her or the next guy from her to giving him head. The near naked guy pulled her panties down; he gave her asshole a spit and slowly started to into her, in a few moments she was taking him in all the way. Watching her was better than the gay guy; she was almost an artist in her own right. When the guy was thrusting in, she would move with the flow and deep throat the man. When he pulled out she moved away from the cock, and her ass would move into the guys cock, it was pure beauty. The guy giving it to her, would slap her ass a bit and go for faster shorter thrusts, her heels would click on the floor. The guy getting head played with her hair, while she tried to keep the rhythm up. I could feel Charles, behind me, rubbing himself up against me, his hands on my hips. I couldn't resist I rubbed his cock with my ass, he started to lift my skirt up, and I felt his cock rubbing on my panties, between the crack of my ass, and I didn't stop it, it felt great. But in all honesty, I didn't want to go further when it came to anal, I wanted that to be special not lost in a porn theater.
The guy getting double teamed got up and left, the girl was getting more, until a new person stood next to us. He tried to feel my legs as Charles was dry humping me, I was scared, didn't know if Charles would be upset this guy was trying something or upset with me for allowing it. As the guy got bolder he pulled his cock out and started to rub against me. "It's ok, I'm here" was what Charles whispered in my ear, he continued to dry hump me, soon my heels were clicking to Charles thrusts, then he did something I didn't know he would do, he whispered something in the guy's ear, I couldn't hear but Charles was now standing in front of me, and the guy was behind me continuing what Charles was doing. Charles and I were kissing, his cock was up against me, forcing my ass closer to the guy, and then I felt the warmth of cum on my ass. Charles sat me down in one of the chairs, and put his cock in my mouth, I was so into sucking his cock, I didn't realize another guy was sitting next to me I slid my feet from the shoes, and knelt in front of Charles just losing myself in his cock, the guy sitting next to me, was standing waiting for his bj, but I wasn't going to do it, I had a focus, I wasn't going to lose it.
"Grab his cock!" was all I heard, looking up he winked at me, I stopped for a second to grab hold of his cock, I went back to work, blowing Charles and jerking this guy off. I could hear this guy asking me to suck him, but I wouldn't until Charles took himself out of my mouth and had me face the other guy, I took his cock and put it in my mouth, just sucking on the head, then going further down his cock, I sucked a little more, I went back to Charles' head, licking and sucking, looking up the were playing with each other nipples, then I felt the tension in Charles' cock, he pushed my head off his cock, and shot a load over my face, that set off the other guy as he unloaded in the side of my face and my hair. I got up, to see the girl still having fun with 2 more guys, as I stood up to get my shoes back on, she waved and gave me a wink, and she went back to work giving a sloppy blowjob.
Grabbing the back pack, Charles led me to the bathroom, after 5 minutes of washing cum off my face and trying to get it out of my hair, and trying to wipe off any dried cum off my ass, we left walking back to the bus station for me to head back home.
"Are you upset with me?" he asked, he took my hand into his.
"What do you mean?"
"For having you give that guy a blowjob and the other guy rubbing up against you."
"Little confused."
"Confused? About what" I could feel a tinge of anger
"Well I thought you and I were on a date, and well it turned out this way. Maybe I read things the wrong way, but I thought you and I were gonna have the fun." As we got to the bus station we sat down.
"Listen, you are awesome to hang with, I really would love to pop your anal cherry and I enjoy being with you. But, we can't date, I'm way older than you, your still in school, we don't have much in common other than sex. Don't be hurt, just being honest!"
I really did want to cry, but I understood what he was saying, but it still hurt.
"You ok? It's ok, to let me know."
"Yeah, I'll get over it! So do I still get shoes for free?" really trying hard not to cry Laughing, "Not all the time, but I think that's doable." With that he kissed me on the lips and held me. It felt good, just being held like that and I looked down!
"Oh shit, I need to change!"
"You better hurry you only have a couple of minutes!"
I hid behind the station, putting my jeans on quick, grabbed my tennis shoes and put them on, `damn the socks' I thought to myself. I stuffed the heels back into the bag, "hurry I can see the bus coming!" I rushed to fix my shirt, wiped the gloss off my lips, fixed myself up, and got my money out for the fare. Went back upfront, looking down the street, I don't see anything "Where's the bus?"
"I was fucking with you!"
I playfully hit, and we sat and talked until we saw the bus coming, he told me to call him if I wanted to, gave me a quick kiss, and he went to wait for his bus, as he saw me off on mine. On the way back home, I had a lot to think about, reaching into my bag, I saw my nails, explains why the bus driver looked at me, I grabbed my walkman and listen to some music, peeling off the nails. Thinking about things, I had fun, would I do it again?
Guess you will have to wait for the next story...
Hugs and Kisses to those who wrote me.
If you like what I wrote please email me at michelebrown@rocketmail.com