Perverts 'R' Us

I Meet the Family, 1965 - Part 1

By Walter Howard ( M/M/F, Anal, Incest )

Author's note: All my stories are semi-biographical. They all happened to me in some way or another. Names, dates and participants may or may not have changed. If you like my recollections, please respond to wahobac@email.com. Thank you.

I was going to meet up with Carlos this afternoon. It had been several weeks and I was looking forward to see what clothes he had bought to dress up in and help along my fantasy of having a cross dressing teen boy friend to play with. Carlos was a 17-year-old Hispanic boy I had met and played with several weeks earlier. He was about five and a half feet tall and was slightly built. He had longish black hair and was shy and lonely when we first met. He had really got into the cross-dressing thing the last time we were together and I had given him his first ass-fuck. I had left him with $50 to buy some more clothes and was anxious to see what he had done with it.

When Carlos opened his door, at first I didn't recognize him. He was damn beautiful. His hair was curled, he had eyeliner on and his lips were a dark pink color. My eyes glanced down to take in the rest of him. He was wearing a sheer black blouse and tight pink hot pants. His legs were covered in black fishnet stockings and he was wearing pink 3-inch heels. I noticed that his legs were clean shaven and I was hoping the rest of his body was too as I followed him back to his bedroom.

He struck a pose by the bed and asked, "What do you think, Walter. Do I look as good as I think I do?"

I told him he looked absolutely incredible and I took him in my arms and kissed him. My arms reached down and grabbed his ass and I pulled him close as our tongues pushed into each other's mouths. I sat down on his bed and held him at arm's length. "Look at you," I said. "How did you do this? You look perfect, better than I could ever have imagined. You are the sexiest thing I have ever seen."

Carlos had a big grin on his face. "My grandma helped me with the makeup and stuff. I picked out the clothes myself." He went on to tell me that his grandmother had found him experimenting with her makeup. After questioning him, he told her about me and that I had taken him out for a date when he was dressed as a girl. His grandmother was happy to hear that he was going out instead of just sitting around all day, and volunteered to help him with makeup and stuff. She told him that he could be the grand-daughter she never had.

"Damn, Carlos, you look good enough to eat. I don't know if I want to take you out and show you off or just fuck the living daylights out of you." I sat down on the edge of the bed and pulled out my 8-inch cock. It was getting so hard so fast that I just had to give it room. Carlos grinned and licked his lips. He started rubbing his crotch and I could see his little hardon outlined through his hot pants.

"Your grandmother helped you look like this?" I asked. "And she knows about me and you?"

"Oh yes. I told her you were a special friend. She works at the Owl Drug store and she said that she sees a lot of male couples in there and they usually seem very happy. She said that she had noticed that I seemed a lot happier the last few weeks, so I told her why. She wants to meet you, by the way. She'll be home in about 15 minutes; will you meet her and say hello and shit?"

Well, this was a twist I wasn't expecting. I hoped that Carlos had told her that I was married. I didn't want to become a family member. I only wanted Carlos for some hot male/male sex when I needed it.

"Sure, I guess so." I said. "So what are we going to do for the next 15 minutes? Look at each other?"

In answer, Carlos knelt between my legs and took my cock into his eager mouth. I lay back on the bed and was just starting to enjoy his face fuck, when I glanced over to the door and was surprised by the appearance of a rather large woman watching us from the hall. I started to rise up and tell Carlos to stop when she entered the room.

"Don't stop on account of me." She said. "I didn't mean to startle you. Just go on Carlos. This must be your friend, Walter, huh? Well, I can see what attracted you to him. He is built rather well, isn't he? Hello, Walter. I'm Carlos' grandmother, Serena. I'm pleased to meet you. Carlos has been looking forward to your visit. Well, I'd better go now. I can see you boys are busy."

"Whoa. That was your grandmother?"

"She's pretty cool for an old lady, huh?" Carlos said as he came up for air.

"Yah, I guess," I replied, still trying to get my mind around what had just happened. I glanced over to the door again and noticed that she had left it open a little bit as she left. Across the hall another door was open a crack and the room behind it was dark, but somehow I just knew that grandma was in there watching us. I tried to remember Serena from the brief moment she was in the room. She was probably about five feet tall and I guessed somewhere in her 50's. She had longish black hair and had big breasts filling out her white blouse. I could see that her hips were wide and round and when she turned to leave the room, her large round ass was stretched tightly over a black ankle-length skirt. All in all, not too bad for an old lady.

I asked Carlos to stop for a minute. I stood up where I knew I could be seen if Serena was watching, and methodically removed all my cloths. I laid back down on the foot of the bed with my legs over the edge which made my stiff cock stick straight up. I asked Carlos to just walk around and pose for me and I slowly stroked myself while watching him strut. He started to slowly take off his cloths and was soon down to just his fishnets and high heels. He had shaved his body and he looked younger that his 17 years. I asked him to climb onto the bed in to a 69 position. He put my cock back into his mouth and I started sucking his balls and fingering his asshole. I knew that Serena would be getting a straight on eyeful of my cock sliding in and out of her grandson's mouth and I hoped she was enjoying it as much as I was. I soon could feel my balls pumping and I shoot a big wad into Carlos' hot mouth. He tried his best, but I was ejaculating faster than he could swallow. Carlos sat up and pressed his ass into my face and I pushed my tongue into his rectum as far as I could get it as cum continued to pump from my cock.

I pushed Carlos off my face and rolled over onto my stomach with my knees on the floor. I spread my legs apart to give Serena a good ass shot. "Your turn Carla," I said. Fuck my ass you hot little slut. I've never been fucked by a sexy girl before. Fuck me Carla!"

I reached down into my pants pocket on the floor and handed Carlos a tube of KY. I didn't know where the "Carla" thing came from, but it seemed right at the time, so I just went with it. Carla lubed up and entered my ass. He started pounding hard and it didn't take long for him to empty his load into my pleasure passage.

"Nice," I said. "Why don't you lay here for a while and I'll go clean out my asshole. Then I'm going to come back and fuck you Carla and make a big mess in your ass."

I opened the door slowly and peeked into the darkened room across the hall. I could see in the dim light that Serena was lying on the bed naked and was shoving a dildo in and out of her hairy cunt. Her thick legs were spread wide and her eyes were shut, so she didn't notice as I slowly open the door and crept into her room. I was standing at the foot of her bed letting my eyes take in her plump body. Her large breasts were jiggling in time with her dildo strokes. Her nipples were large and sticking up out of her tits. She had a nice soft roll of belly over her swollen pussy. The inside of her thighs were smooth and round and fully packed.

She was quietly moaning as she continued to fuck herself oblivious to the world. I didn't want to scare her, but I wanted a taste of her pussy, so I knelt between her legs and cleared my throat. She jumped and her eyes flew open. She started to close her legs and I reached out and held them open.

"Let me help." I said quietly as I took the dildo in my hand and started stroking. She looked at me with a questioning look on her face. I smiled and told her to just relax and enjoy. She lay back down on the bed and I started stroking the inside of her thighs with my other hand as I continued to push the dildo in and out of her juicy cunt. I climbed up onto the end of her bed and lifted first one leg, then the other over my shoulders and leaned forward and put my mouth right over her clit. I continued fucking her with the dildo and started sucking her clit in and out of my mouth. I reached up with my free hand and took a soft tit in my hand and started squeezing it and playing with her nipple.

My tongue was licking, my mouth was sucking, one hand was massaging titty, and the other hand was dildoing and soon she started bouncing her fat ass up and down on the bed and then flooded my eager mouth with her sweet juicy climax.

"Thanks, Serena. I enjoyed that and I think you did too." I licked the sweet juice out of her twat, and then kissed the soft insides of her thighs as I extracted myself out from between her chubby legs. "You did a wonderful job on Carlos and I really appreciated it."

"Thank you, Walter." She breathed, "I haven't come like that for a long time. I didn't know if I ever would again. Thank you."

I left and shut the door and rejoined Carla in his bedroom. He looked at me and asked what took me so long. Then he must have smelled pussy on my face, because his eyes got big and he said, "Did you do something with my grandmother?" I could see that he was upset so I told him that I didn't screw her or anything, I just helped her masturbate. He didn't understand that someone as old as his grandmother could have sex, so I had to explain to him that as long as a body is able, it is do-able. "Besides, she was watching us through your open door. She got excited watching our young male bodies and needed to get off."

"Now it's my turn to fuck your tight ass, Carla." I said as I lay back down on the bed. "Come over here and straddle my cock you sexy thing."

He turned his back to me and stood over my erection. I coated his asshole with KY and he sat down on my rod. It met with some resistance as I hadn't open him up with my fingers, but he kept pushing down and suddenly his rectum relaxed and he was sitting on my stomach and my cock was buried in his ass as far as it would go. He started moving up and down slowly and my cock was coming almost all the way out, then back in. I watched for awhile as my cock slipped in and out of his cute little asshole, then lay back down again as he increased his motion. I glanced over to the door as it opened and Serena walked in.

She had put on a low cut nightgown and it was open in the front allowing her big breasts to hang free. She winked at me and came over to the bed. Carla saw her too, but he was too engrossed in what he was doing to stop. She knelt between my legs and took Carla's cock into her mouth. This was just too cool. Granny sucking off her grandson while I'm fucking him in the ass. Can it get any better than this, I wondered.

Well, it could. I asked Carla to get off me and I told Serena to sit on the floor at the end of the bed. I then had Carla spread his legs and face her holding himself off the bed with his arms. Then I re-entered Carla from the rear and Serena took his cock back in her mouth. Now I was controlling the rhythm and with each stroke I was shoving Carla's prick into Serena's mouth. I felt Carla's ass pucker up and I knew that he was shooting into his grandma's mouth, and I wasn't going to be able to hold it for much longer.

At the last possible second, I pulled out and grabbed my cock and aimed under Carla's ass so I could shoot my hot cum all over Serena's tits. Then I moved away and so did Carla. There was Serena sitting on the floor with my cum all over her neck and breasts and Carla's spunk dribbling out of her mouth onto her chin. I knelt to one side of her and started licking our cum off her hot body. I noticed that Carla knelt on the other side and he too started cleaning off granny with his tongue. I paid special attention to her nipples, sucking them deep into my mouth. I then leaned up and kissed her and she opened her mouth and sucked my tongue deep inside.

"Damn," I exclaimed as I broke the kiss, "That's more fun that a body ought to have. I'm drained."

"Come to the kitchen," said Serena. "I think we could all use something to drink. I know I could." She got up and left the room swaying her big hips from side to side. I put my cloths back on and Carla got some things out of his drawers, and looked like Carlos again. I didn't say anything to him as we walked to the kitchen, because I knew that he was still processing having his cock sucked off by his grandmother, and then licking her titties.

Serena had buttoned up her see through nightgown and had three big glasses of iced tea waiting for us. I downed mine is a few gulps, and she quickly refilled the glass. "It was nice meeting you Walter," she said as she sat down next to me at the table and kissed my cheek. "I haven't had any sex like that since my husband was killed in Korea 12 years ago. Now that you have reawakened desires in body, I don't want to let it go again. I think I'll ask Carlos into my bed tonight. What do you think about that, Carlos?" she asked as she winked at him.

Carlos still looked uneasy, but he mumbled something affirmative when the phone rang. Serena answered it and immediately started talking in Spanish to whoever was calling. She hung up excitedly and told Carlos that his cousin, Emil, had fallen and possibly broken his wrist and Emil's mother didn't have a car and wanted Serena to take her and Emil to the emergency room. Serena didn't know what to do because her car was in the shop. Both Serena and Carlos looked at me and I shrugged my shoulders.

"Why don't I take them in my car?" Serena went to get dressed and Carlo washed the makeup off his face. We hopped in my Chevy station wagon and they directed me to Emil's house.

In part 2 of this story, I find out that Emil has three sisters age 13, 11, and 5 and all kinds of fucking possibilities open up for me as I meet the rest of the family