New adventures in a new home. Again, there is background, so if you don' t like that, please skip.
As I mentioned before, from the time I was 13 to the time I was 18 my mom and I moved three times. For two of the moves, even as we moved in, I knew we were going to move out before too long. On top of that, I was almost insanely horny. Like most teenage boys, I could have four or five orgasms a day without even getting sore.
When I was 16 we moved from the tidy neighborhood of bungalows and small houses I discussed in House One to a two flat in a more “urban” neighborhood. The neighborhood was very dense, with lots of apartment buildings, and was very diverse. There were people of all races, with immigrants from Haiti, the Caribbean, West Africa, Korea, and Central Europe. Quite a difference from the previous neighborhood!
When we moved to the two flat I had just gotten my driver’s license. This was a big improvement from the old neighborhood in that I could travel where I wanted, when I wanted. My mom still worked long hours, so I was able to cruise the neighborhood and get the lay of the land. Just to the east of us the neighborhood was a little rougher and denser. To the west of us the neighborhood was less dense and had large Korean and Jewish populations. Four blocks either way was an entirely different place with entirely different people, and I loved exploring each.
One evening I was rolling through the neighborhood to the east of us. There were groups of Caribbean and West African immigrants hanging out, playing music, and having a good time. It looked like fun, and I decided to stop and check it out. I parked and walked a few blocks over to the celebration. I stuck out like a sore thumb, since I was young and white, but as I danced and sang along, people treated me as if I belonged at the little street party. I even had a few glasses of Jamaican rum punch.
As I was leaving I was feeling good, and maybe a little tipsy. I was walking down the street toward my car when I realized that there were four or five women slowly strolling up and down the block. They were all black and wore tiny miniskirts, high heels, and different sorts of tank tops. Even I, as a 16 year old, could figure out that these were prostitutes. Knowing that there were prostitutes on the loose, and being a little tipsy, I had an instant erection.
As I started to walk the block the prostitutes were strolling, they noticed me. All of them smiled, winked, and said suggestive things.
“Honey, you want a blowjob?”
“Come on baby, I’ll suck your dick.”
“You ever fuck a sista, white boy?”
I mentally responded to each question. Yes, I wanted a blowjob, yes, I wanted her to suck my dick, and no, I had never fucked a black woman. But I sure wanted to. Still, I was scared, having heard that prostitutes would rob you, and knowing that prostitution was illegal. I was on my way past them when I saw Shandra.
Shandra was about 25, and wore black latex boots over her knee with six inch heels, white thigh high stockings, with a garter belt that showed from the bottom of her tiny, tiny grey miniskirt. She was probably six feet tall in her boots, and had long, long legs. She wore a bright pink tube top that contrasted with her caramel skin. Her breasts were easily D cups, and swung free under the tube top. Her hair was cut short and died white-blonde. She wore almost no make up. She was stunning.
Shandra strolled along next to me for a whole block, teasing me the whole way. She kept asking me if I was a virgin, and if I wanted her to wait while I went to an ATM. I joked back with her, but she was definitely making me very, very horny. Sadly, I knew that I had no money and no way to get any money. She was killing me.
Suddenly Shandra got quiet and slipped between me and the fence. She kept glancing over her shoulder and was obviously trying to use me to shield her from something. I glanced over my shoulder with visions of Guido the Killer Pimp stalking us. What I saw scared me even worse. Two police cars had stopped on either end of the block we had just left and the police were rounding up the prostitutes.
“Do you have a car, baby?” Shandra asked.
“I do, but I really don’t have any money” I replied.
“Well, that’s OK with me. I need to get out of here before those police see me. I’ll make it worth your while” she cooed.
I might only have been 16, but even I knew that as soon as we drove away from the police Shandra was going to be done with me. I quickly weighed the risk of getting caught with her in my car versus the benefit of gaining a little more time to see if I could fuck her. As always, the little head won, and I decided to give her a ride.
“Come on. I am on this block” I said.
As we ducked into my car Shandra looked over her shoulder. The police were sweeping the sidewalk with a spotlight, looking for more streetwalkers. She slid into the passenger seat as the light hit me in the eyes. I covered my eyes and kind of waved, the way white people do when the police are bothering them. I gave the sort of wave that said “Hi Officer! Everything OK?” Since the police were clearly there for the streetwalkers, this wave worked just fine.
“So, where do you want to go?” I asked.
“Well, I’ve got a spot where I was working, but there are too many police out tonight. I don’t work all the time, and getting arrested would make this a waste of my time and money. What are you up to now?” she asked.
I was nonplussed. What was I up to? Really? I was 16 and broke. I couldn’t exactly take a six foot black prostitute to the Baker’s Square could I? Still, my mom was gone for the weekend, and we did have some vodka in the apartment. If I could get Shandra into the house with nobody seeing, I might be on to something.
“Look,” I said “I have to be honest. I am 16, and broke. I’m not really ‘up’ to anything. I was going to go home and make a nice vodka drink and watch a movie until I met you. So, I’m not really sure what to do now.”
Shandra smiled at me with the sweetest smile you’d ever see on a hooker. She introduced herself, and then explained that she “worked” to make ends meet when things got tough. On a night like tonight she was perfectly happy to just be off the streets and not subject to arrest. She also told me that she was 19. I kind of doubted everything she said, but I didn’t think I cared.
“Are your parents home?” she asked.
“No. They are gone for the weekend” I replied.
“Well, I like that you were honest, and you are doing me a favor. Besides, you’re kind of cute” she said. “Mind if I come over, have a drink, and watch a movie with you?”
The whole situation was disorienting. She was still a prostitute, and I was not na? enough to think that I was going to score with her for free. On the other hand, why didn’t she just tell me to take her to her car, or somewhere else, get out and abandon her promise to “make it worth my while?” What was going on? Did she want to come in to the house to rob me there? As I was thinking all of this I glanced over and realized that with her legs slightly parted I could see that Shandra was not wearing underwear, and what her pussy was shaved bare. We immediately headed to my apartment.
We weren’t far from my house, but we made a little small talk. My mind was still reeling, but I was working to keep my head in the game. Hookers don’t give it away for free, but why were we going to watch a movie? Shandra was explaining that she didn’t live in the neighborhood, but that when she needed some extra money she would come out and spend a few nights turning tricks. I just nodded stupidly. Again, I was not sure I believed it at all, but what was I going to say?
As we arrived at the apartment I sort of reverted to acting as if Shandra was not a hooker. I was so nervous that I just sort of acted like Shandra was a date or something. I opened the door for her, took her purse, and offered to make her a drink. She giggled.
“You are so cute. You know that when guys pick me up they are all business. Look how sweet you are” she said.
Shandra took her drink and smiled sweetly at me and I had an instant throbbing erection.
“What movies do you have?” she asked.
“I was planning on watching European Vacation or Pee Wee’s Big Adventure, but we have some others” I replied.
“Ooo, let’s watch European Vacation” she said.
I did have one porn movie, but since I had not suggested it, and since she had chosen European Vacation, Chevy Chase and Beverly D’Angelo it was. I popped the movie into the VCR, grabbed some microwave popcorn from the kitchen, and my drink and we started to sit down. I sat on the couch facing the television and Shandra smiled and sat so close to me that our hips were touching.
“You really are a gentleman, aren’t you?” she asked.
I was feeling like a doofus, rather than a gentleman, but I just sort of smiled and said “Well, why not? If I did not want to be a gentleman I could have left you on the street, or dropped you off somewhere else.”
Shandra smiled at me again, and as the Griswald family flew over the Atlantic, Shandra started to rub my cock through my clothes. As soon as her hand touched the outside of my pants my cock felt like an electric shock had gone through it. Still, I knew that I did not want myself to get into a situation where I owed Shandra money I didn’t have. As sweet as she was, I didn’t want an angry prostitute in my apartment.
“But, I really can’t . . .” I started.
“I know you don’t have money. This night has been a complete waste of time for money, and now I am going to enjoy myself” she interrupted as her head slipped down, so that my cock was even with her mouth, even if it was still in my pants.
I felt my zipper drop, and cool fingers wrap around my cock. Then Shandra’s very warm mouth and tongue engulfed my hard on. Her mouth was very wet, and she worked her mouth all the way down to my balls. I felt her warm tongue flick out and lick my balls. My eyes rolled back in my head and my right hand traced her spine until my hand slipped around her sweet ass and my finger rubbed the outside of her bare cunt.
Shandra kept my cock buried in her throat for a long time while I rubbed her very wet cunt. I was getting used to the feeling when she suddenly pulled up with a swirling sunction, keeping just the tip of my cock in her mouth. Then she twisted her head as she swallowed my cock again. She repeated this over and over as I grabbed her ass and started squeezing and kneading her ass. I could feel that my cock was going to explode and warned her. She pulled up so that my cock was half in her mouth and sucked hard. I exploded with cum shot after cum shot. Shandra stayed on my cock, sucking the cum out of me. When I was done cumming she slid her mouth up my cock and let my very wet, very limp cock fall from her mouth. Then she looked me in the eye, opened her mouth to show me my cum, then swallowed it right in front of me. Then she smiled.
My head was swimming, and every fiber in my body made me want to jump on Shandra. I slipped off of the couch and knelt facing her. She immediately swung her legs over to straddle my head. For a split second I considered what eating a hooker’s pussy might not be a good idea, but her wet, shaved slit was staring at me, brown on the outside, pink on the inside. Her white stockings made a great contrast with her caramel colored legs. I knew I was going to eat that pussy.
I grabbed the heels on Shandra’s boots and spread her long legs up and out. I plunged my tongue into her gash and ran it up and down from her asshole to her clit. Then I sucked her clit into my mouth and worked it with my tongue. Shandra was grunting and humping my face as I released her clit and started to tongue fuck her. I grabbed her by the hips and lifted her up so that I could work my entire face into her cunt. I could feel her body stiffen and her stocking-clad thighs clamp around my head as she came. I kept my tongue in her and lapped out all of the sweetness that poured from her.
I came up for air as Clark W. Griswald was accidentally knocking Stonehenge over. Shandra’s eyes were rolled up in her head and her tongue was licking her lips. I kept firm pressure on the outside of her cunt, just above her clit. Miriam had taught me that this could help an orgasm linger for a woman, and it appeared to work on Shandra.
As she came back down from her orgasm Shandra asked “Why don’t we move to a bed, where we can get a little more comfortable.”
“Sure, but can you leave the boots and stockings on?” I asked.
“They make me feel sexy. You like me in them?” she replied.
I guess the look on my face told her that I thought her boots and stockings were very sexy.
I led her by the hand into my mom’s room. My mom had a king-sized bed, whereas I had a twin. I was going to want room for this.
I sat on the bed and gently pulled Shandra toward me. I lifted her tube top and her big breasts bounced out from under them. I started nibbling just below her belly button and worked my way up and I massaged her breasts in my hands. By the time I was standing in front of her I was holding her breasts in both hands and alternating sucking one nipple, then the other. Shandra’s head was thrown back and she held my head in her hands. I cool smell the light musk coming off of her skin, and could feel the light sheen of sweat between her breasts. It was intoxicating.
I slid my hands down to the back of her skirt and unzipped the zipper. She wiggled her hips and the skirt fell to the floor. Shandra stepped closer to me and pulled my shirt over my head. Then her hand dropped down and finished opening my pants. As my pants fell to my ankles, I stepped out of them and grabbed Shandra’s ass as I nuzzled her neck and ear.
“I need you to fuck me now” she whispered in my ear.
I turned her so that the bed was behind her and pushed her onto her back. I grabbed her heels again and pushed up while spreading her legs. Her eyes flashed and I could tell that she was almost as horny as I was. I grabbed my cock and slid it deep into her cunt. She was very warm, and very wet. Still, her cunt was so tight that it felt like I was fucking a fist.
I hammered Shandra’s cunt from above while I slipped my right fingers into her mouth and grasped her ankle with my left hand. As she got closer and closer to cumming I pulled my fingers from her mouth and wrapped my hand around her throat. Another trick Miriam had taught me. As soon as my hand wrapped around Shandra’s throat she started to buck and cum. Her eyes grew wide and her thighs tightened around my torso. I could feel the slick coolness of her stockings rub against me while the walls of her cunt massaged my hard on. I fought not to cum immediately.
As Shandra was trying to catch her breath I pushed her ankle away from her body, and grabbed her right ankle to flip her over. I grabbed her hips and pulled up. She spread her legs and lowered her upper body so that her ass was jutting up in the air. I grabbed the garter belt around her waist and rubbed the head of my cock against her slit. She humped backward, trying to pull my cock into her. I put my hands on her ass cheeks, pulled her open, and slipped into her cunt from behind. I reached back up with one hand to grab the garter while I used my thumb from the other hand to massage her asshole.
Shandra spread her legs wider and I started to pound her from behind. As I pushed my thumb further and further into her asshole, she moaned and yelled into the pillow. I felt her cunt tense up again and finally lost my control. I shot my load deep into her cunt as she ground herself on my hard on. As I slipped out of her well-oiled cunt, Shandra squeezed her legs together and rolled on to her side. She was flush and glowed with a film of sweat from our acrobatics. I laid down next to her and pulled her close.
“You have been with someone older, haven’t you?” Shandra asked.
“Why?” I replied.
“When I was 16 I fucked 16 year old boys, and I have fucked older men since. Most 16 year old boys don’t eat pussy like you do. They don’t push on the top of the clit like you did. They don’t grab my throat and put their fingers in my asshole. Older men, who know how to make women come do” she explained.
“Uh. Well. Yeah. There was a lady who taught me a lot, I guess” I said.
“She did you a big favor, baby. You can call me to fuck any time” Shandra said as she started to get out of the bed.
I watched her put her tube top and tiny mini skirt back on. I was getting hard again watching her. She smiled at me and motioned me toward the edge of the bed. She knelt in front of me as I sat on the bed, and lowered her tube top so that her tits were exposed. She spit on her hand and started to work my cock up and down. She stroked me while she banged my cock against her tits and occasionally licked the underside of my cock helmet. She stared at me the whole time. All to quickly she could feel my cock starting to pulse. She knew I was going to cum. She smiled with a twinkle in her eye and sucked my cock into her mouth as I blew another load into her. Seeing as how it was my third orgasm in about an hour, there wasn’t much cum left in me. Shandra swallowed it and winked at me as she stood up and walked out of the room.
I followed her in a daze. She was writing on a pad in the kitchen. “This is my phone number, baby” she said. “My momma might answer, but just ask for me any time you want to fuck like that again.”
With that she walked out of the back door and down the stairs. Her footsteps had long stopped echoing when I realized that I probably should have asked her if she needed a ride. Instead, I locked the door, turned off the television and went to sleep.