Trained by the Neighbors: Shopping


It felt like I had just fallen asleep, when I felt the bed jostling. In the darkness, I could feel Sam’s body getting under the covers with me. I rolled over onto my back, and he laid on top of me, his lips covering mine and his hands going to my nipples.

We kissed for a long while as I felt his hard cock pressed against my leg. He moved from my lips to my neck, kissing, nuzzling, and biting it. My own dick was hard now too.

He moved down to my nipples. I loved the feeling of his lips around them, the way he sucked and bit them. I started moaning, and my legs spread even wider. I wanted him in me.

He must have felt my need and rolled off me and onto his back. “Climb on, baby girl,” he whispered. I straddled him, and he pushed his cock up into me as I lowered my ass onto him. My asshole protested, but I knew that the pain would soon leave and that wonderful feeling would come back.

I started sliding my ass up and down his cock, my hands on his chest while his hands pinched my nipples fiercely. “Ride my cock, bitch,” he moaned. I bounced on his cock faster, grinding my ass onto his raging cock on the down stroke. My dick would rub against his belly when I did, and his cock was making wonderful sensations in my ass.

At some point, the combination of his cock slamming my ass, my dick rubbing against his belly, and his rough treatment of my nipples was too much. I slammed down onto him and cried “Oh, DADDY!” as my dick began spraying cum all over his belly and chest. The orgasm overpowered me and I couldn’t move, but he began thrusting up into me hard. As the last squirt of my cum trickled onto his belly, his cock began shooting it’s load deep inside me.

It would have been nice to savor the sensation of Sam pumping his load into me, but I was still mind-numbed by the power of my own orgasm. As his cock slowly stopped spasming in me, I collapsed onto him. “God, daddy, that was fantastic!” I said, breathlessly.

He didn’t respond, just wrapped his arms around me. He held me as his cock deflated, finally popping out of my asshole accompanied by a flood of cum. I could have fallen asleep right there, in Sam’s arms.

“Ok, baby girl,” he said, “I gotta go to bed and you need to go to sleep.” He rolled me off of him and got out of bed, then leaned over and gave me a quick kiss. “Sweet dreams,” he said, tucking me in and leaving the room. I dozed off happy.

My ass was still tender the next morning when Debbie woke me up. Jim’s cock had really pounded into me last night, and I had ridden Sam’s cock hard. My poor little asshole was paying the price. I smiled, however, at the dried cum on me.

Debbie was happy and bouncy, her full tits swaying in her nightgown as she stood next to the bed. “We’re shopping today!” she exclaimed. “Get up, get up!”

I got up and went to the bathroom, then asked Debbie if it was time to get Sam up. “No,” she said, “let him sleep in today. I’m sure he won’t mind missing his morning blowjob since he got a piece of ass from you last night.” Debbie took me into the bathroom and both of us showered and shaved our bodies. Again, I took delight at soaping up Debbie’s large tits.

“Do you like them?” she asked. I nodded, and she said “We can see about getting you some nice titties…maybe not as nice as mommy’s, but anything would be better than that flat chest you have now.” I looked down at my chest, and it was still a flat boy’s chest. Debbie reached over and tweaked one of my nipples. “Although,” she continued, “you have pretty large nipples for someone who used to be a boy.” It was true, my nipples were kinda bigger than most boys, and it was a source of teasing that I got from the other guys in PE.

We toweled each other off, and Debbie made me pay special attention to her pussy. I thought she wanted to cum, but when I leaned over to lick her pussy, she stopped me. “No time for that now, sweetie. There’s shopping to be done!”

Debbie laid out panties, a bra, a long skirt and a blouse for me. I put them on, loving the feeling of feminine clothes, and did my makeup and hair without any help. Debbie was proud of me, but still made a few minor corrections.

As we walked to the front door, I had a panic attack. Over the last two days, I’d become comfortable, even happy, wearing women’s clothing in the house. The front door, however, represented a new territory to me. I stopped and grabbed Debbie’s hand. “Mommy,” I said hesitantly, “what if someone sees that I’m a boy instead of a girl?”

Debbie ran her fingers through my hair. “Sweetie, the only way they can tell is if you get a hardon. Otherwise, you look like a little hottie. I wouldn’t be surprised if some guys hit on you.” I was a little reassured, but still afraid.

We walked out of the house, and drove to the mall. I was still panicky when we walked into the mall and headed for the first ladies apparel store. As she browsed, I walked quietly behind her, my head down. I just KNEW that everyone knew that I was a boy wearing girl’s clothes.

Debbie giggled and leaned over to me. “The manager is checking you out,” she giggled. I looked over and saw a middle aged, slightly portly man looking at me from a doorway in the back of the store, a grin on his face. “Give him a little show…..wiggle your butt a bit when you walk.”

I tried to put a little more into my walk. Debbie had taken a blouse from the rack, and dropped it. “Sweetie, pick that up for me please,” she said. I bent down, bending my knees, picked it up, and handed it to her. “No,” she said exasperated. “Like this.” She dropped the blouse again, then bent over from her waist, her ass plainly visible and highlighted. I noted her position, and glanced over to the manager. He was talking with one of the clerks and hadn’t noticed it.

We browsed around some more, working our way over towards the manager’s office. He was still talking with the clerk, but glanced in our direction every so often. I told Debbie, “He’s still watching us.” She giggled again and said “Ok, give him a good look at your ass.” She dropped another piece of clothing on the floor, and I copied her earlier movement. My ass was pointed in the manager’s direction, and Debbie whispered “He’s definitely checking your ass out. Good girl!”

Debbie had picked out some clothes for me already, and then suddenly got a strange expression on her face. “Follow me,” she said, “and do what I tell you to.” I trailed behind her as she walked over to the manager.

“Hi!” she said, in a happy voice. “I have a question for you.” The manager smiled and said “Sure. How can I help you?” Debbie put her arm around me and said “My niece is visiting from out of town, and I’d really love to send her home with a lot of new outfits. Unfortunately, I’m a bit short on cash today. Is there any way we can get a discount?”

The manager smiled and said, “For two lovely girls [he must have been talking about Debbie’s body, since her face was, to be kindly, unspectacular], take 10 percent off.” Debbie stepped up to him and said, “I was hoping for more. What would we need to do to get a bigger discount?”

The manager suddenly swallowed and turned pale, realizing what she was suggesting. He paused, and thought for a minute. Before he could answer, Debbie said, “We REALLY would be appreciative if we got a nice discount from such a sexy manager.”

He stammered, “Uh…why don’t we step into my office and discuss it?” Debbie smiled, took my hand, and led me into the office. The manager followed and closed the door.

“So, how big of a discount are you looking for?” he asked. Debbie smiled and unbuttoned her blouse. Her bra-covered tits looked ready to spill out. “How about 50 percent?” she said, cupping her tits. I was a bit shocked, and the manager wasn’t too far behind me.

The manager glanced over to me. His cock was straining against his pants, and suddenly I wanted it. Debbie pushed him back into his chair, and said “Mindy, take care of the nice man. I dropped to my knees in front of him. While Debbie pushed up her bra to free her tits, I unzipped his pants to free his cock.

“Uh, ma’am, maybe..” he stammered. Debbie silenced him by standing next to him and pressing a nipple against his lips. As his greedy mouth covered her nipple, my greedy mouth covered his cock.

He had a much smaller cock than either Sam or Jim. It was a lot easier to suck it, and I was really enjoying running my tongue up and down it. The manager was moaning into Debbie’s tit, and his cock was throbbing in my mouth.

He didn’t last long. He gave a muffled bark as his cock pumped cum into my mouth. I kept sucking him harder, needing every last drop out of his balls and into my belly. When his cock stopped, Debbie giggled again and pulled me up, kissing me, sharing his cum. The manager watched us kiss, his cock twitching down to softness.

“Fifty percent it is,” he said, out of breath. “In fact, it’ll be fifty percent any time you come in here and ‘discuss’ it with me, lady. Your niece can really suck a mean cock. I bet you’re pretty damn good yourself.” Debbie broke the kiss, and put her tits back into her bra. She pulled some tissue from her purse so I could dab up the cum on mine and her lips, then buttoned her blouse back up. “You’re such a nice man to say that,” she said, leaning over and kissing him on the forehead. “Isn’t he, Mindy?” I gave a shy smile and nodded.

The manager tucked his cock back into his pants, then slowly got up. Making sure that it wasn’t obvious that he’d just gotten blown, he led us out back to the store. The clerks gave him a strange look at the sight of us coming out of his office, and an even stranger look when he told them about the half-off discount. He disappeared back into his office while Debbie proceeded to buy half the store, it seemed. The total damages for all the clothes she bought for us was over $500, AFTER the discount.

Laden down by bags, she turned to me, winked, and said, “We’ll have to come back another time and see how much of a discount we can get from the other stores here.” We loaded up the bags in the car, then drove home.

On the drive, Debbie asked me “Do you feel more comfortable about your dress now?” I said, “Yes, I do.” She reached over and gave my leg a squeeze. “Good. Now, we’re going to have to explain this to Sam when we get home. He’s not going to be happy.”

Sam was up when we got home and Debbie’s prediction was right. He was upset at the cost, and bitched loudly at Debbie over the cost. She promised that we would make it up to him and that I really needed clothes. He just grunted at her, still pissed off, but the damage was done and there wasn’t much he could do about it.

After dinner, Debbie and I tried on the clothes and did a fashion show for Sam. He wasn’t as impressed at the clothes, but he know how a good time Debbie was having. After the last of our outfits were displayed, Sam told Debbie, “Ok, it was all very nice, but let’s get back to that ‘making it up to me’ part.”

Debbie pouted, but he was adamant. “Ok, what do you want?” she asked. He motioned her to come over in front of him. She walked over and dropped onto her knees. “Nope, the other end,” he said with an evil glint in his eye. “Pull your skirt up and your panties down.” “Let me at least get out of these new clothes,” she whined. “No,” Sam responded. “Get that ass out in the open.”

Debbie sighed, and got on her hands and knees in front of him. Sam dropped to his knees behind her, spit on the tip of his cock, and shoved it into Debbie’s ass in one move.

“OOOhhhhh, you bastard!” Debbie yelled. I noticed that she didn’t try to pull away, however. Sam immediately started pounding her ass hard, his cock slamming in and out of her ass. “I HATE .. it when .. you grudge-fuck .. me!” Debbie said between clenched teeth.

Sam pounded her ass while I watched, my dick getting hard at the sight. Debbie was trying to hold her clothes out of the way so nothing would get on them, while Sam sawed his cock in and out of her. I could see the shock ripples in Debbie’s ass every time he slammed it into her.

He finally gave three sharp shoves, then held his cock deep into her as his cock erupted in her ass. Debbie had a look of pain mixed with bliss on her face, and her legs were shaking. “No, don’t stop!” she cried. Sam cruelly yanked his cock out of her ass, cum dripping down onto the floor from her asshole.

He reached up and grabbed a handful of hair. “Next time you’re going to spend so much, at least call me first, ok?”

Debbie nodded, then stood up holding her clothes so that none of his cum would get on them. “Come help me, Mindy,” she said, walking towards the bathroom. I glanced at Sam, still on his knees on the floor, his deflated cock still covered with shiny cum. I really wanted to go clean Sam’s cock wth my mouth more than I wanted to help Debbie, but Debbie gave me a sharp look. “MINDY! Come with me!”

I followed Debbie into the bathroom, and helped her clean up. Getting out of her new clothes and putting her nightgown on, she said “God, I hate it and I love it when he does that. He’s so manly and sexy when he’s like that, but damn my ass hurts. Come here and make mommy forget about her sore ass.”

She sat on the edge of the tub and spread her legs. I crawled between her legs and under her nightgown, and my tongue reached out for her pussy as her hands grabbed my hair and pulled my face in. She was already turned on, and it only took a minute before my tongue centered on her clit and she was shaking from a strong orgasm. Her grip on my hair loosened, and she sighed. “You’re such a good girl, Mindy. Mommy’s glad.”

I sat back and looked up at her. “Can I go take care of daddy now?” I asked with a grin. “Yes, sweetie…but be careful. He’s still in a bad mood.” I was more than happy to risk it, and almost skipped out of the bedroom to the living room where Sam’s cum covered cock waited.

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