The Homeless Peeper II
by twistmynipples
Tracy was pretty wild in bed and was very open-minded. There wasn’t anything she wouldn’t try twice. We had done sex in every position imaginable, I’d fucked her ass (she’d never done that before she met me and turns out she was a natural). I had been very innocent and na? when we first met; every new act we tried was always a first for me. It was for that reason that I was not overly shocked at Tracy’s latest proposal. We had just had a wonderful time one afternoon. It hadn’t been anything too wild; I fucked Tracy up the ass. We did that at least 3 times per week and it wasn’t getting old; we both loved it.
“Fuck, Don. That was great. It’s the wildest feeling to feel you shooting your cum in my ass.”
“It feels pretty good being the one who’s doing the shooting, too,” I replied.
We laughed together and Tracy spanked my ass.
“You’re bad!” she chided.
“I was an innocent little homeless kid until I met YOU,” I laughed and again she spanked me.
“Let’s go. The kids are going to be home soon. You better get going. I have some ideas for new things to try.”
“What? Care to elaborate?”
“I’m still planning. You just bring your open mind and we’ll have a blast – or rather YOU’LL have a blast and I’ll enjoy feeling it.”
I laughed, kissed her deeply and left. We had been able to keep our relationship a secret from my Mom and Tracy’s kids for 8 months and we didn’t want to risk anything. I walked the 10 blocks home and watched TV and worked on supper ‘til Mom came home from work.
“Hi, honey.”
“Hi Mom. Did you have a good day? I’ve made us tacos for supper. It’s all ready. I even poured you a glass of wine.”
“Thanks, hon. I’ll just change and be down in 2 minutes.”
Mom came down and we ate supper together. I made supper for us at least half the time. I’d learn to cook pretty well since Mom and I had got back together. I made tea for both of us and we sat and talked while we drank out tea.
“Donny, we have a pretty close relationship, don’t we?”
“Sure, Mom. I value our relationship more than anything.”
“That really means a lot to me. We don’t keep any secrets from each other, do we?
“No, Mom. I tell you everything.”
“The reason I’m talking like this is because one thing we have never discussed is girls. You never talk about girls at school. As far as I know you’ve never had a date. Am I missing something?”
I have been dreading this moment for 8 months. I knew it was going to come up SOMETIME, but I had no idea how I would handle it. I didn’t want to lie to Mom, but I could NEVER tell her about the things Tracy and did together. I thought for a moment.
“Is this a subject that we won’t connect on, Donny? If it is I’m fine with that; it’s just that I want us to be very open with each other. The odd time I have a date, you always hear about it.”
“It’s not that I don’t want to share it with you, Mom. It’s just very hard for me to discuss girls with my mother.”
“I understand, Donny. You’re probably afraid that I’ll judge you or try to impose restrictions on you, right?”
“That’s some of it.”
“Well, you’re almost 19. You’re a man and it’s not my business to control you anymore. I can merely offer guidance. The final decisions on everything in your life lie with you and only you. How ‘bout this? When we’re talking about girls, I’m not your mother, I’m just a friend. Can we try that?”
“Yeah, I think I’d be willing to give it a shot.”
Mom gave me a big Mom hug and Started to cry a bit.
“That makes mo so happy, Donny.”
“Me too, Mom”
“Can we start this new chapter of our relationship now?”
Again I worried about how I’d handle things, but I’d come this far.
“Sure.”
Mom took a deep breath.
“Do you have a girlfriend?”
“Yeah. Kinda.”
“What do you mean kinda?’
“Well… uh… uh… this is really hard, Mom.”
“Just relax, Donny. I’m not Mom here, I’m Donna.”
“Okay, Donna. I am seeing someone, but it’s nothing super serious. It’s just… ah… it’s… just…”
‘Friends? Are you just friends?”
“No, Donna. It’s just sex.”
This caught Mom off guard, but she quickly got herself back together.
“OK. How long have you known her?”
“We’ve been doing it about 10 months.”
I was surprised that the words came out of my mouth and I think Mom was, too.
“Oh. So you were together with her before we got back together. What’s her name?”
‘Damn. This could get messy’ I thought.
“Let’s just call her ‘T’”
“K. Are you and T happy with your relationship?”
“Very happy, Mom. We’re both enjoying each other a lot. I’m pretty sure that we love each other, but both of us are happy with our ‘Friends With Benefits’ relationship.”
“I’m glad you’re happy. This is really great. You’re in a happy relationship and I’ve been talking with Tracy a fair bit about HER sex life and let me tell you. Happiness doesn’t even BEGIN to describe her relationship.”
I was fighting to stifle the humongous smile that wanted out.
“When we get together she spends at least half the time telling me about how great this guy is. She won’t tell me his name, but she tells me EVERYTJHING else. It sounds very wild and interesting.”
“Cool. I’m happy for her.”
Mom kissed my forehead and went to get up but before she did I spoke up.
“Wait. Wait. Wait. You got ME to open up. Now it’s YOUR turn, Donna.” I said with a laugh.
“You don’t mean… No. I can’t tell you about MY personal life. No.”
“Come on, Donna. If I can open up, you can, too.”
Mom sat and pondered my wisdom for a bit.
“Okay. That sounds fair and it’s pretty easy for me. Since you and I have got back together I’ve been on 4 dates and they were the first dates I’ve been on since I had shitbrick arrested.”
We both laughed.
“That’s a good name for him.”
Again Mom went to get up, but I grabbed her hand.
“Uh, uh. You’re not done yet, Donna.”
“What do you mean?”
“You’ve got more to tell.”
“Do you mean I have to tell you about my SEX LEFE?”
“Yep. You got it outta me. What’s fair is fair.”
“Fine. I haven’t been laid in over 5 years.”
Before Mom was even done the sentence she turned as red as a beet.
“Are we done now?” she said.
“Yeah, I guess so,” I giggled. “We gotta get you some, Donna.”
“DONNY! Okay, talk time is over. I’m MOM again!” she said with a laugh.
The rest of our night went as normal and life settle back into its regular rhythm. One exception was that Tracy seemed to be a lot hornier when we’d get together. I didn’t think anything of it; just thanked whoever or WHATever was causing it. Life was good. Then came Friday.
Tracy and I were laying on her bed panting and gasping and trying to recover from a hot and sweaty session
“I don’t know WHAT it is that’s got you so hot and bothered the last week, Tracy, but DAMN! It’s nice,” I chuckled.
“I’ll tell you THIS much, Don. The reason I’ve been so randy is from thinking about my plans for this weekend. Monique and Leo are going to spend the weekend with their aunt and I have some plans for us, hon.”
“Is it anything I should know about?”
“You’ll find out when the time is right. I just finalized things today and finished getting what I need to.”
“Wow! Plans AND new purchases. Should I be excited or scared?” I said with a smirk.
“Excited, honey. WAY excited. I’ll pick you up from school and we’ll eat dinner around 6:00.”
“You say excited, but I FEEL scared. I’m just kidding. I trust ya.”
We kissed and fondled each other and then it was time for me to leave. We got dressed, cleaned up her room and I walked back home.
That night, Mom knocked on my door as I was playing on my computer.
“Can we talk, Donny?”
“Course, Mom. Come on in.”
“This is a ‘Donna’ talk.”
I swallowed hard. I still wasn’t quite used to this new fold in our relationship, but in most ways it felt good.
“Okay, Donna. Have a seat.”
“It’s nothing too major, Donny. I just wanted to let you know that I have a date tomorrow night. I’m going out about 8 and I might be late. I don’t know.”
“That’s cool. I gotta date, too. I’m meeting my babe for dinner and then who knows what?”
Mom giggled.
“Okay. You just be careful with the WHAT?”
“Uh, excuse me, Donna, but that was a ‘Mom’ sentence.”
We laughed.
“You’re right. I hope ya nail her good,” Mom said. Still laughing. “I can’t believe I said that. You have fun and treat her right.”
“Yes’m.”
Mom left and I went back to playing Civilization.
Friday went like any other day. I went to school and Tracy picked me up as usual. When I got in her car, I reached over and put my hand on her leg with the idea of starting something. She picked up my hand and moved it back over.
“Not, now, Babe. We won’t do THAT until after dinner.”
Now I was confused. We’d been fucking like rabbits every chance we got for months and now this change. We chatted as we drove to Tracy’s place. After arriving Tracy directed me to her entertainment room.
“You pick out a movie and I’ll get us each a beer. I feel like an action movie.”
I rooted through her extensive DVD collection and picked one I hadn’t seen, ‘Cliffhanger’. It looked like it would be good. I like Stallone. Tracy returned with the beers and then the movie started.
“Oooh. ‘Cliffhanger’. Great choice.”
She leaned over and kissed my cheek. I turned to extend the kiss, but she turned away.
“Gotta wait a few hours, Baby.”
The movie ended and Tracy made me dinner. We ate, but all I could think about was what was coming later.
We finished and we cleaned up the kitchen together. It was about 7:00. Tracy led me into her family room and rewarded me with a very deep kiss. My eager tongue invaded her.
“Mmmmm. I’ve been wanting this all day,” I moaned.
“I think your wait will be well worth it.” Tracy replied.
I went to take off her blouse, but she stopped me.”
“You just stand there. I’ll do everything, honey.”
She kissed me again and her kisses trailed down my neck. She nibbled my earlobes and seductively pulled my shirt over my head. Her tongue made random paths across my chest and back as I just stood there. She stopped at my nipples and sucked them gently, at first, but gradually increasing in aggressiveness. She came back up and kissed me.
“Enjoying yourself, lover?” she asked.
“Uh huh,” was all I could squeak out.
This was very different that usual. Passion usually drove our encounters, but today was seductive and erotic. Tracy continued to kiss me, lick me and suck my nipples. I had no idea how long it went on for, but after an eternity she undid my jeans and slid them down my leg. I hadn’t worn underwear that day, so my hard cock immediately sprang up when she pulled my jeans below it. Tracy giggled.
“Fuck I love your perfect cock.”
Soon I stood before Tracy, fully nude with a quivering cock. She went back to kissing me, licking me and sucking me everywhere; everywhere, that is except where I REALLY wanted it. She would NOT touch my cock. She touched all around it and she blew on it, but she would not touch it, no matter how hard I begged.
“Now we try something different,” Tracy whispered in my ear and she went to her dresser, opened a drawer and pulled something out. I couldn’t see what it was, but I knew I’d find out soon. She sashayed back over to me.
“Shut your eyes, lover.”
I did and I felt her lips upon mine once again. The kiss lasted only a short time and Tracy moved away.
“Close your mouth now and keep your eyes SHUT.”
I did and felt a cloth over my lips and then she tied it behind my back. She had put a gag on me. This was getting KINKY.
“Okay. You can open your eyes.”
I did and saw that Tracy was holding something else. She saw me looking and held it up. It was a black mask.
“I’ve always had this fantasy about being raped by a masked man. Tonight that will happen.”
Now I understood. I understood everything except for the gag. I made some noises and pointed at the gag.
“Why the gag? Easy. If you talk to me then I know it’s you and it spoils the fantasy.”
Sounded plausible. I was getting into this now. My cock was back at full staff. It had been a little unsure about things, but now it felt comfortable.
Tracy moved closer and pulled the mask over my head. There was a hole for my nose and 2 small holes for me to see out and 2 others over my ears, but that’s all.
Tracy went back to kissing, sucking and licking my neck and body. I went to move to the bed.
“No. You keep standing there. If you move before it’s time, the night ends.”
I stayed exactly where I was and Tracy continued her actions. I was getting so turned on it almost hurt. My rigid cock felt like it was going to explode. Then I heard a noise.
‘Shit!’ I thought. ‘That’s her front door.”
Then I heard footsteps. They were coming up the stairs. I made a noise and pointed at the bedroom door. Tracy stood up and pointed at me, shaking her head. She went back to her previous actions. The footsteps were coming down the hall and then they stopped at the door. I could tell it was a woman that entered, but that’s all, seeing as it was dark in the room, save for the candle in the corner.
“You’re right, Tracy. He’s got a magnificent cock.”
Holy FUCK! This was my Mom! I stepped back and tried to cover my cock, but was answered by a slap of Tracy’s hand on my ass. I went back to standing there.
“It’s been so long since I’ve seen a real one that I almost forgot how beautiful they are.”
“I don’t lie, Donna. I’ve got the perfect man here.”
That statement made me feel good, but this was my MOM ogling me! She walked around me and as she did she stroked and caressed my ass.
“Nice tight ass, too. You got a hot one here, but why the mask?”
“I thought the anonymity would be an extra turn on for you.”
“Oooh. Kinky. I like it. Would you tell me your name, kind sir?”
“He can’t talk either.”
“Oooooj. The kinkiness deepens,” Mom giggled.
Mom’s hands left my ass and made their way around to my front. She began to rub and fondle my chest and nipples.
“He LOVES to have his nipples played with – HARD,” instructed Tracy.
Mom started to pinch my nipples.
“I’ve never don’t THIS before,” Mom giggled. “It’s fun and a real turn on for me. I’m surprised.”
Mom’s pinches got harder and soon she was squeezing my nipples with what must have been close to all her strength. I was loving it. I was starting to forget this was my Mom doing it to me.
“Will he do what I say?” asked Donna.
“If he knows what’s GOOD for him he will,” Tracy chuckled.
“Put your arms around me. Caress my back and shoulders.”
I did and Donna did the same to me. She nuzzled my neck and started kissing and sucking it.
“He doesn’t like marks being left, Donna. No hickies. We’re not in high school anymore.”
“Mmmm. You hold me good. I want YOU to take charge now. Undress me and have your way with me. I’m ready for you.”
My mind was a jumble. I was having enough trouble concentrating enough to keep standing let alone comprehend all that was happening.
I reached down and unbuttoned Donna’s blouse, pushing it open to reveal her breasts. I cupped each one and stroked it over the bra. I reached behind her and undid the clasp. My eager hands went under the cups still hanging loosely from her shoulders. I molded and groped her melons. They were bigger than I thought. I’d say maybe a ‘C’ cup but she had the hardest nipples I’ve felt. Tracy had much bigger nipples, but Donna’s nipples felt like they’d cut glass. They were about as big around as a pencil and just as hard, too.
“Damn! That feels good,” Donna moaned.
I removed her blouse and a small shrug by Donna made her bra hit the floor, too. I leaned down and sucked a nipple into my mouth, sucking hard.
“Oh YES! Suck me. Nurse me. Just like you’re a hungry baby.”
This weirded me out a bit.
‘That’s EXACTLY what this is.’ I thought.
I sucked her nipples for all I was worth while I squeezed and rubbed her ass. She reached down and undid her pants and in short order I had them down at her feet. I was now caressing her bare ass. I felt around some and realized she was wearing a thong. I kissed my way lower and pulled off her thong with my teeth. Then I made my way back up her legs with my tongue. I licked and kissed her inner thighs.
“Oh fuck yes! That feels so fucking great!”
I pushed her back and she fell onto the bed. I glanced over and saw that Tracy had removed her clothes and was sitting in a chair rubbing her pussy.
“Don’t look at me. Concentrate on Donna. Make her feel as good as you make ME feel, lover.”
I looked back at Donna who was laying on the bed with her feet over the bottom edge still touching the floor.
I resumed my position between her legs and continued to kiss and stroke her inner thighs. I slowly made my way up taking special note of the musky aroma drifting from Donna’s nether regions. I breathed deeply.
“Oh yeah, Baby. Eat her! Eat her GOOD,” moaned Tracy.
I licked my way along the crevice at the top of her leg and I was now less than an inch from her steaming pussy. My tongue extended from my mouth and I lightly touched her pussy lip.
“Oooooo FUCK! YES!! YES!!!” Donna yelled. “I need that sooo fucking BAD! Eat me, please. PLEASE eat my cunt.”
That was weird. Hearing your mother say the word ‘cunt’. If I ever said it, I’d be slapped for sure, but it was hot hearing Donna say it.
“Eat my fucking cunt! PLEASE!!” she repeated.
I traced a light path up her puffy pussy lip and back down the other one, being careful to avoid her clit. Donna squirmed her hips on the bed.
“Please don’t tease me. Just EAT me!”
I made my way back up her lips and stopped at her clit. I breathed on it and blew air over it.
“Oooook YES!” Donna moaned loudly.
Then my tongue made first contact. It reached out and flicked itself over her hard clit.
“YEEESSSSS! hissed Donna.
I licked her clit gradually increasing my tempo and strength. Then I took her throbbing clit in my mouth and sucked it for all I was worth.
“YES! YES! FUUUUUUCK! YES! I’M CUMMING! YES!!! EAT ME!!! YEEEEEEEEES!”
Donna was bucking her hips wildly in the air as I sucked her. When she was done she collapsed in a whimpering pile on the bed. I looked over at Tracy and she was wildly rubbing her pussy and clit. I nodded at her.
“Yes! Get over here and do the same to me! Eat me! NOW!”
I quickly crawled over to Tracy and dove upon her waiting pussy, pleasuring her as I had done MANY times before. It took less than a minute to have Tracy moaning and screaming.
“YES!! Eat me! Make me cum, fucker!! Eat my pussy hard! YES!! I’m there!! EAT ME! I’M CUMMING!! YEEEEESS!!!”
With all her motions during her orgasm she slid off the chair and landed in a pile on the floor. I looked back over at Donna and she was sitting there watching her friend finish her orgasmic convulsions.
I crawled back over to Donna and stood up. She knew what to do. Her mouth pounced upon my quivering cock and she sucked for all she was worth. Her hands snaked behind me and grabbed my ass. She pulled me closer to her as her head bobbed back and forth on my cock. Then her hands left and I felt hot breath on my ass. Tracy was behind me and she began kissing and biting my ass a Donna sucked my cock.
After a while I pushed Donna back on the bed and pulled her legs apart.
“Oh yes! Are you going to stick me with your pole?” Donna squealed, grabbing her ankles and spreading her legs wider.
I plunged my cock into her in a way that would be defined as FAR from gentle.
“Uuuuuuugh!” grunted Donna as I immediately began to pound my member into her sloppy pussy. She grunted with every stroke and was soon screaming the most obscene things to me. I can’t even remember what they were, but I do remember being very shocked at thr words coming out of my mothers’ mouth.
I tried my best to delay my climax until after Donna had cum, but because of how excited I was I didn’t last as long as I wanted. I began to grunt and thrust into Donna’s pussy harder and soon my cock erupted inside her. The very second I started Donna started her orgasm as well.
“Yes! I feel you cumming in my slutty cunt! Yes! Fill me up! I’m your bitch! FUCK ME!! FUCK MEEEEE!”
I fell onto her and she hugged me deeply again whispering her extremely naughty thoughts in my ear. We hugged and fondled each other for a long time. Tracy was involved in this, too. We were a mass of three wanton bodies and I had 2 beautiful women at my sides.
“I better be going,” said Donna. “I have to get home to Donny. He had a date tonight, too. Hope he had a good time.”
“I’m SURE he did, Donna,” chuckled Tracy.
Mom moved over to me.
“Thank YOU, sir. That was the BEST I’ve EVER had. Can I see you now?” she said, reaching for my mask.
I panicked and my eyes got as huge as saucers. I looked at Tracy for help.
“No, honey. That’s the deal. Besides, maybe you don’t WANT to know who it is. Hell, for all you know that could be your SON!”
‘What the FUCK are you saying?’ I screamed inside my head.
You’re right,” Mom laughed. “Better I don’t know. But Donny? You’re EVIL!”
Mom got dressed quickly, but just as she was leaving she walked past me and with one hand spanked my ass and with the other squeezed a nipple.
“I sure hope I get to see YOU again someday.”
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