(This is part three. Parts one and two were MM theme)
I should have known that my liaisons with Bob would be noticed. He had sent me home with a set of tools with removable handles. The file set handles were red and rubbery and surprisingly versatile for use as butt plugs, hidden in plain sight, or so I thought. I enjoyed inserting them in my ass and discovered I wasn’t as straight as I thought. I loved the penetration and fullness.
Bob had changed my life. My white-haired elderly neighbor had given me a tour of his garage a few weeks before, and I had ended up mesmerized by his bisexual porn stash and when he whipped out a veiny cock with an angry plum tip, I succumbed to lust and became his cocksucker. (See Old Bob)
Later, he invited me to relax on the couch in his garage and after a beer and another porn, I was again his slut. He got us both naked and worked his cock up my ass. For a man in his late 60s he was a virile lover. (See Old Bob, Again)
I was shocked that he had this spell over me. Now I can’t help but get erect when I soap myself in the shower. I take extra time with my butthole, and last week I borrowed my wife’s Nair and removed all the hair of my crack and balls. I’ve been straight all my life but suddenly a grandpa had flipped a switch in my brain.
With the weekend came time alone as my wife and teen kids were often out. Bob was out of town, and he and I kept our connection on the down low anyway, so I had planned a great session of ass play as soon as my wife left. She had taken the dog for a walk and when she got back she was heading out for the day, meeting friends across town.
While my wife was on her walk I had already taken a larger handle from the tool set and worked it up my ass. I couldn’t believe how sexy it felt to be stuffed like this, with the flared base of the handle snug against my cheeks. I had on athletic shorts and t shirt and acted normal. I worked in the garage and as my wife returned I noticed her stopping at Bob and Ann’s house, chatting away with Ann. They had hit it off at the block party and had become fast friends. Ann was maternal and caring, and they actually seemed to be getting close. Bob had become close, and I wanted more.
I put it out of my mind as my wife entered the garage and surprised me. “Hey sweetie, Bob is out of town and Ann needed some help with a repair. I told her you could help since you didn’t have much going on. Sound good?”
I was happy to help. Maybe it would be a kind of payback since I was having sec with her husband. Then she added, “It involves a leak so she needs you right now, can you head right over?” I started to go and she stunned me by adding, “Oh and she said Bob had loaned you some kind of tools and you will need those. I gotta go.” She took the dog and went inside.
My heart sank. Ann knew about the tools! Shit. Shit. The garage door was open and Ann was visible in her yard. Shit. Well, I decided to go with it. Maybe I’m overthinking it. I convinced myself to play it cool and act normal.
I grabbed the file set and wondered what would happen with one of the handles buried up my butthole.
========
My mind raced as I tried to act casual. If Ann was on to me she didn’t act like it. “Thanks for coming over,” she said sweetly.
She led me inside and paused as we walked by the kitchen counter. “You can set those here,” nodding to the file set, “We both know I don’t need them.” Her eyes bored into mine. I was frozen. She studied my face. “Don’t you have anything to say?” Her normally innocent grandmotherly tone was gone. She looked the part of stern matron. My stomach lurched and instantly knew my precarious position. She had me.
Our brains can work so fast. In a flash I was seeing her in a new light. She actually looked a bit like the actress Kathy Bates, with pleasant eyes, and, a hint of a southern accent. She was plump, rather pear-shaped but with a pleasantly narrow waist before the flair of her big ass. I could see that in younger years she might have been considered attractive, bright eyes, and surprisingly full lips, framed by a modern trim of her hair that was white and lightly peppered black.
I took in her large, pendulous breasts under the denim shirt she wore with her granny jeans, which were tight against her wide hips and generous ass. It struck me as funny that she was wearing those spongy Crocs shoes, just like a grandma. There was nothing funny about this, however.
“Well?” She smirked just like her husband. “Cat got your tongue?” She was toying with me.
After my silent, stunned pause she barked, “Let’s go mister.” She directed me to the back bedroom and had me stand between their king sized bed and wall mirror. Their room was like my parents, floral bed spread and outdated oak furniture.
“We need to get some things cleared up between you and me. I’m sure Bob has filled your head with lies,” she stated matter of factly, with less anger than I would have expected.
“First, out with it,” she demanded and held out her hand. “Uh, excuse me?” I stuttered weakly in reply.
“If that is the game then, fine, here,” she stepped towards me quickly and twisted me around before I could react. In one motion she bent me over at the waist, on to the bed, and my ass was up. I was horrified. I was also turned on as hell. Why would I let this little woman take charge? My mind flipped back to Kathy Bates, a strong no-nonsense woman.
“You perverts like a strong hand so let’s get this out in the open,” she calmly narrated as she yanked my shorts over my butt. I could not believe what a sick and twisted world I was in after living a straight and normal life for 45 years. This grandma had exposed my butt and the red-handled homemade butt plug, given to me by her husband. I couldn’t speak, but this humiliation prompted a word from my mouth. “Please,” I muttered.
“Please!?” She laughed. “I thought so.” With that I felt her delicate hands rub my bottom, and her toned changed to a soothing but leering tone, “I hoped so…” she seemed to linger as she rubbed my ass lovingly, pausing at the red plug and tapping it, sending bolts of lust through my loins.
“I didn’t think you’d be so willing for me, or for Bob. Maybe it will go better for you this way. You and I can have a special time together. “ With that she smacked my ass hard, harder than I thought a woman like her could.
“What do you say, should we have some special time together?” Smack! Smack! I was sure my broad white ass was bright red. “Yes,” I whispered.
She grew stern: “You will say, ‘Yes Miss Ann.’” She didn’t sound happy. Smack! “Yes Miss Ann,” I whimpered.
She kept fondling my ass. “Such a big strong husband.” Smack! “If your wife only knew,” Smack! “how much you want it like this.” Smack! I let out a small groan and she chuckled. “Let’s see if I’m right.” She reached between my thighs and massaged my balls on the way to fondling my penis, exploring it’s hardness, and running a finger over the slit to catch the cum leaking. “Oh yes, your penis is enjoying our special time.” Smack! Her spanks sent jolts to my cock.
She pulled my erection backwards till I felt it would break. “Look at yourself,” she commanded. I turned my head and in the mirror I could see my my white ass, pale and exposed. I could see the bright red hand prints on my ass and even my cock and balls, looking so tight and purple, peeking through my thighs.
She pulled my shorts all the way down. “Hmm, no wonder Bob wanted to plow that butt,” she hummed and she kneaded my round buns. Growing up I had been embarrassed by such a large butt and thighs, often being teased in school for my “black girl booty.” High schoolers can be cruel. While I had since grown into an adult and my height had diminished the obvious proportions of my ass, I still carried the childhood humiliation.
“Looks like you got all clean back here too,” she noticed my shaved crack and I felt her fingers on the plug. “I’ve got something better than Bob for this,” she hissed as she started pulling and pushing the plug. I groaned. “Oh you and Miss Ann are going to be special pals,” she kept talking about ring special. I wondered how she knew of me and Bob. I wondered what was better than Bob.
I couldn’t think too much since she started fucking my ass with the plug. I grunted with the thrusts. “Oh you will like Miss Ann.” She went back to my balls and cock while she fucked the plug in my ass, gently tugging my cock at the tip, milking it backwards. “Let’s keep this ass busy. I’m gonna love watching you eat your cum. You’ll eat your cum for Miss Ann, won’t you.” I was already being trained and replied automatically, “Yes Miss Ann,” which brought a happy hum from her as she worked my behind.
“That should be enough for now,” she paused. I was still on edge, incredibly turned on but wondering what revenge she had in store for me cheating with her husband.
I stayed put, bent at the waist, as she undid my shoes and stripped my shorts and socks. She playfully tapped my balls and pulled on my cock. “Close your thighs, your cock and balls need to be pointing out at me.” I clamped my thighs and felt a little pain in my balls from being pressed backwards. It was incredibly erotic.
I could hear rustling and turned to see her taking off her clothes. She had pale creamy skin, nice skin I thought, for a woman in her late 60s. She was plump, but smooth, and her belly looked a little round but not flabby, almost muscular like a farm woman. She had a full bush, a mix of pepper and gray.
She caught me staring. Smack! “You don’t spy on a woman, not without permission,” she laughed. “Alright, let’s see what we’ve got. On the floor, on your knees,” she ordered. “W-where?” My voice was still weak, I was still hesitant, knowing she had the power.
“Remember how you kneeled for my husband? My goodness, you were sniffing his cock like a whore in heat. He does have a nice cock. Let’s see if you like doing the same for Miss Ann’s pussy. You’ve been a bad boy and gotten me all wet.”
In a haze I obeyed. She had me strip off my shirt, and I knelt before her, plug stuck sensuously in my ass, both of us completely naked now, my face at her full bush. I could see her large outer lips below her bush, and sensed a heat wafting to my nose. The aroma wasn’t unpleasant, but I was confused, trying to process what she had said. She knew about me and Bob, and it seemed these two had a perverted relationship, both very dominant.
“Do what you did for Bob. Smell Miss Ann,” she placed a hand on my shoulder. I moved my nose into her bush, remembering to pause and stay still, breathing on her. My nose rested in her hair and I inhaled deeply. She smelled similar to my wife, more musky, and I found I wanted to devour her. My cock felt ready to explode. I pressed a little forward and looked up at her.
“You like my pussy?” She leered down at me, hungrily. “Yes Miss Ann,” I panted.
I took my time, drifting my nose lower and breathing gently as my nose traced her big lips, my tongue barely touching her outer lips. I was delighted to hear a soft moan from her and her hand grip my shoulder. I wanted to please her.
Her pussy smelled sweeter than I imagined, a little tangy, a hint of sweat and even a very light scent that I decided was urine. I had no idea why this combination was electric. It was extremely feminine, natural. For a woman her age I was surprised by how youthful her pussy tasted. I felt I could cum at any time.
I traced her outer lips and planted light kisses next to, but not on, her pussy, between her legs and pussy, which my wife enjoyed. I could feel her wetness on my cheek. I lightly dragged my lips across her open slit, she had meaty lips, like she had a lifetime of being fucked hard, and I gently took each lip in my mouth, and in doing so my nose grazed her clit. “Mmmmmmnnng, very good boy. You are a good boy. Someone taught you to take your time,” she panted. “You like being my good boy?” I pulled my face gently away, and huffed, “Yes Miss Ann.”
Her hand shoved me back. “Enough. Back on the bed, ass up. Time for your punishment.” She laughed and added, “Let’s see how agreeable you really are.”
As I climbed I saw my reflection and noticed my naked body and ass. I waited with my head down and ass up. I heard dresser drawers open. Something jangled like a belt. She rustled through and said, “This oughta work.” I felt her footsteps and she halted behind me. Your penis is bigger than Bob’s. This should work.”
She gripped my cock from behind and then pain! She had thumped the tip of my cock, hard! The sharp pain caused my erection to wilt instantly. In a moment I felt cold metal and my cock and balls were being put in a lock of some sort. My balls felt tight and exposed, sticking out due to a metal ring around their base. My tip was held tight against a small cold cage. My shaft had disappeared. “All my sissies like being caged,” she said flatly, “and I imagine you’ll soon love it.”
Caged? Sissies? My mind raced and I tried to picture the device, maybe I had seen it on some porn, but needed to check. I pushed my head under to see if I could get a view but my belly blocked my shrunken cock. She noticed and chuckled. “You will figure it out, now hold still while Miss Ann climbs on.”
The bed shifted with her weight and I felt her hands flat on my ass. She pressed me lower till I was on my belly. The plug was removed with a jolt. My rectum felt suddenly open. Then her weight was on me, her meaty thighs straddling me. A broad cold pressure pushed against my anus. Oh no. She was entering me with a strap-on. She pulled back out. “Here,” and she grabbed a pillow and shoved it under my belly, changing the angle.
She pressed back on me, straddling me again and my sphincter slowly accepted the tip of whatever it was she was using. I grunted as the tip popped through my anal ring and a warmth flooded my body. I was stretched full but the pain eased, and I could feel the tip going deeper in my bowels. I was strangely proud to take the dildo. What had happened to me? My shriveled cock felt tingly and tight against the metal of the cage. I was sure it was leaking all over the pillow.
“There you go, take that cock,” she hissed as she pulled back out and started a slow rhythm. I still grunted with each thrust and let out a squeal when she went a bit too strong or deep. “Take your punishment. Take it,” she moaned, and in the middle of her opening my butthole I wondered how the strap-on pleasured her pussy. “You bad boy, fucking my husband. I’ll teach you to love my cock more. I’ve got more cocks to use on your cute buns.” I believed her. The pain was nothing compared to the fullness and utter depravity of a grandma fucking my ass.
Lost in my thoughts I was suddenly smacked on the ass, hard! Whap! Whap! “I was talking to you boy!” Oh shit, she cruelly plunged harder, rearranging my guts, “Uhh, mm, uhhh, Yes, uhh, Yes Miss Ann,” I managed to utter between thrusts. “Yes, what? You little sissy!” Her tone was cruel, mocking. I loved it.
My brain shouted at me to hold out, but I was surrendering to her. “Yes, oh, uhhh, fuck, I uh, oh, I love, oh shit, uhhh, oh my God, uh, I love your cock Miss Ann.” She didn’t seem content. “More?! More than Bob’s!?” I saw stars and the pain mixed back in. Sweat was on my brow. Everything was blocked out but her commands. “Yes! More! I love your cock more!” I panted.
Her thrusts continued, and she shifted her weight subtly, and, oh fuck, I curled my toes and bit my lip. I realized she had found my prostate, pummeling it, as I felt I had to either piss, cum, or both, even as my cock was caged. It was amazing. “Ohhh, uhhhh, more, yes, uhh, more than Bob’s,” I moaned again, and my words sounded distant, so filled with lust, out of body, as I listened to some man craving to be fucked. My brain shouted that the lustful sissy was me. I was being programmed to love a good butt fucking.
She paused and reached between my legs. I felt her fingers catch the drippings of my cock. “Give me your mouth.” I turned and she rubbed her fingers on my lips then pushed them in my mouth. “Suck your cum.” I moaned and slurped my tangy discharge. She repeated this a couple of times, ensuring I tasted myself. “That will do for now.”
For a grandma she was so strong. I was putty in her hands. She plowed me for a while longer then slowed to a stop. She was short of breath but seemed triumphant. She leaned forward on my back, pressing her swinging tits on my back, I could feel her rubbery nipples. The strap-on changed angles painfully, I yelped, but she continued to lay on my back, our sweaty bodies pressed together and I could feel her hot breath on my shoulder. She bit my shoulder, “You are mine now. You belong to Miss Ann. I am gonna mark you as mine.” I groaned in pain and pleasure.
She rolled off my back and the strap-on plopped out. I was relieved of the pain but felt empty. I already missed the fullness.
“Get on the floor.” I flopped on the floor and for the first time saw the tool that had punished my ass, a large black penis. It pointed out menacingly. “Clean it.” She barked. She plunged the rubber phallus into my mouth and I gagged on my ass juices. She held my head as she fucked my mouth.
Temporarily satisfied, she pushed me back, a string of spit dripped between the black dildo and my bottom lip. “Face down. Ass up. Spread your cheeks.“ I complied. She spit her commands and then spit on the red plug that started it all, quickly pushing it back in, my stretched hole taking the plug more easily, but still with a sense of fullness I was learning to crave. “Crawl,” was all she said and then she walked slowly away. I followed liked an obedient pup.
I crawled behind her and lusted after her. I watched her naked form as she led me to main bathroom down the hall.
Her broad white ass and creamy skin were sexy as hell. For her age she had no blemishes. Maybe it was the plug filling me, or the cock cage that stimulated my cock with the crawling, or even her aroma lingering on my face from the quick pussy licking, but I wanted her so badly.
Crawling behind her I thought of planting kisses on that skin. Seeing her barefoot and naked was thrilling. I studied her nice shoulders and back (again, my brain thought, like a farm woman she had some muscle tone to offset any flab) and her waist was narrow before her hips rounded sensuously to that gloriously big and round behind. Watching that butt sway I imagined burying my nose in the crack of her ass, and remembered her large grandma tits. Oh I wanted to suck her tits.
She directed me to their step-in shower, and, after we both entered she once again directed my face at her pussy. “You will serve this pussy.”
She looked down at me with proud eyes. “You’ve been a good boy. A good sissy.” She leaned down and lifted my chin, and soon we were French kissing, she held my chin and searched my mouth with her tongue. She broke off the kiss, “Mmmm, I’m gonna love having you as my sissy.”
Her hand reached for my head and gently stroked my forehead. “Time to mark you as mine.” Her words were curious, but I didn’t care. “Open your mouth and be a good sissy for momma.” I expected to taste her pussy. What I didn’t expect was to be hit with a hot stream of piss on my face! I flinched and was immediately slapped on the cheek, “I said open! Take momma’s pee, and look at me. I want to see your eyes. Show me you will be momma’s good sissy.”
The hot shower streamed out and I caught much of it in my mouth, which soon gurgled over. “Swallow it.” She grabbed my face and I tried not to choke as the forbidden liquid slid down my throat and filled my belly. This was depraved. I opened my mouth to receive more, her stream painting my face and chin, piss running down my body. I gulped as my mouth filled and gasped for air after swallowing. Would it ever stop? My cock betrayed me. I had never felt so sexy in my life.
What was wrong with me? I’m getting off pleasing her like I did her husband. I figured I should seek therapy; being a willing submissive to these elderly neighbors, and now her momma and sissy talk, was sick and twisted.
Her pee dribbled to a stop, and I gasped for breath. She stepped into my face. “There. You helped me with my leak just like we told your wife,” she cackled at her own joke then turned dark and threatening, “You are my sissy now. Never forget it.” She grabbed my head and pulled my face to her bush. “Finish me.”
For the second time I was at her pussy, and this time was more urgent and her scent more pungent. I buried my nose under her gray hairs and nuzzled her her big lips hungrily.
I nibbled my way up to her clit and lightly sucked and started moving my face side to side, holding her clit with increased pressure from my lips, coating my face with her juice. This was a move my wife taught me, slight pulses of tongue on the clit, pressure, slight side to side, moving slow, gauging her reaction. I was so turned on. I wanted to jerk my cock with my face in this gloriously maternal pussy.
“You keep this up and momma is gonna cum. You want to make momma cum?” She cooed, and oddly her tone seemed like she was singing me a lullaby. She had stopped calling herself Miss Ann. Stopped calling me boy. It was driving me wild, and pleasing her sent a thrill to my balls. It took all my concentration to keep my slow, leisurely pace that was having such a powerful effect on her.
I looked up at her and saw her tugging her rubbery nipples, so pink, erect and surrounded with large lightly pink areoles. Her hanging tits had light blue veins against pale skin. I groaned into her muff seeing those large udders. I wanted to suck them so badly. She panted, “Make momma cum.”
She grabbed the back of my head and applied pressure and I took the cue, pushing my whole face against her vulva. She shifted her legs, moving one to the side of me, and pressed me lower, my neck was straining and she mounted my face and started humping. I was lost in her juice, her hairy bush and the perverted scent of urine, her wet lips and clit. I was breathing her aroma in. I may have worshipped her husband’s cock, but I certainly wasn’t gay. She was a woman, no matter how old, and I was luxuriating in her scent, wanted my face painted with her cum. I was hers.
With her powerful and thick thighs straddling my face, she now rode me with a fierceness, “Oh my good little sissy girl, momma’s gonna cum, momma’s gonna nnnnnnggggg…” she stopped talking through deep breaths and shuddered against my face, grabbing my head and shoulder. I was in paradise.
She stopped shaking and stepped back, looking down at me and her fingers wiping some of her cum from my nose and lips before making me suck them clean. “I can see why Bob likes you. You make an old woman feel special.” She bent over and I met her kiss. She held my face and between kisses muttered about “good sissy,” and “good girl,” more kisses then, “made momma feel special.” I wanted her swaying tits in my face and whimpered. She must have sensed this.
“You have been very good. Let’s take care of you.” She stood and I started to stand too. “Uh uh,” she chided with a finger to my lips before I could stand. “You were good today, but you still were a bad little girl for sucking papa’s penis without permission.” I stayed on my knees.
I wondered if she had some more punishment in store for me. She obviously had a plan to increase my humiliation, moving from boy, to sissy, and now I am her girl. She grabbed a couple of towels and led me to the family room, me crawling behind her.
She motioned me to an old fashioned couch and she set the towels down and then sat like she might be reading a magazine. Her tits almost sagged to her lap. I let out a small whimper watching her sit, and seeing them sway, those big pink nipples begging for attention.
I noticed reading material and her glasses on the end table nearby, and I had a flash image of her nude just like this and wearing reading glasses. Holy shit that would be so hot. In a blink of an eye I was her college grandson sent to explain his failing grades to her, after Grandma Ann and Grandpa Bob had helped fund my studies. I would love to have her look at me over her glasses, putting her magazine down, nude and ready to scold me.
Snapping me out of my fantasy she said, “You’ve been good so momma will take care of you,” she patted the couch like I was a puppy.
She indicated where to sit so I climbed up, the cage and plug shifted uncomfortably but the entire seen was incredibly erotic.
She extended her arms and soon her intent was clear- I was to lay face up, resting my head on her lap, looking straight up at those swinging milk bags. My caged cock was on full display, with the ring around my scrotum tightly pushing my balls out while the tip pressed against the cage, some of the skin of the tip pushed through the gaps in the cage. It was humiliating to see it in such a small cage.
“You have a very nice clitty. It is no longer a penis,” she said, reaching her cold hand to flick the cage and massage my caged scrotum and tip through the gaps in the metal. I groaned and thought I might cum. “From now on we will call it your clit. You are my sweet girl. I will help your clit since you’ve been very patient, so let’s help you finish. What do you say?” I stuttered, “Uh, yes Miss Ann.” I waited to see if she accepted my answer or if she would slap my face or cock.
I must have looked ready to flinch, because she kept one hand on my cage and with the other propped my head and said, “I think we’ve gotten better acquainted, don’t you? Why don’t you call me momma,” and then guided my head to the erect pink nub at the end of those pale and veiny breasts. I was able to say a muffled “Yeff mommmuh” as she pressed my mouth to her breast and I latched on, looking up at her face for a signal. The weight of her breast on my mouth felt wonderful. “Go ahead and suck on momma,” she whispered as she applied pressure to my head and I started to nurse, I sucked like I needed comfort rather than sex.
“Oh you chose the right way to suck momma’s tits. Such a good girl.” With that she traced her fingers over the tip of my penis under the cage and smeared my leaking cum around the cage. I moaned on her tit, and she looked down at me and took both her hands and started flicking the cage and cupping my balls. Then a hand reached lower and started pumping my ass with the plug.
Her new position mashed her tit heavily on my mouth and face. She kept flicking the cage and pumping the plug as she pressed her tit on me. She repeated this until she felt my cock flexing, getting close to orgasm. I sucked her tit with her instructions. “Suck momma harder, oh that’s a good girl. You like that cage while momma rubs your clit, oh, so good to have you chew momma’s nipples…cum for momma. We will feed you your cum. Soon you will only need the plug to cum. Shoot your cum on momma’s hand.”
Her dirty talk did the trick and I spurted and groaned and some spurts made it my belly. “Oh that’s a lot of cum.” She withdrew her tit and brought her cupped hand to my mouth.” Be a good girl and eat your cum for momma.” She took her hand full of my cum and my mouth instinctively opened as she poured the creamy liquid into my mouth. “Swallow.” I didn’t need to be told. She cleaned the dribbles that leaked out and had me clean her fingers. I was totally obedient to her commands.
“Let’s get you showered and send you back home.” She turned back into the sweet matron, helping me to the shower, letting me walk upright now.
We showered together, this time I towered over her. She was still in charge as we soaped each other, and she reached to my neck to pull me in for lots of French kissing, mixed with her perverted talk. I tasted her mouth lovingly and let her flick my cage and knead my buns.
After drying off I was expecting to have the cage removed. “Oh, no, the plug and the cage stay,” she said calmly. “What!” I exclaimed loudly and immediately she smacked my face hard with her open hand. “On your knees sissy!” she bellowed.
I obeyed, whimpering, my eyes wet with tears. This wasn’t just a sexual game anymore, this was my marriage. How could I explain the cage to my wife? How could I explain that our elderly neighbor Ann had the key?
“Momma has a plan. I’m sure your wife will be very agreeable. Bring her over to me tonight and I’ll explain it all. I want you both showered and ready. You’ll tell her we have to have a special dinner together, I insist.” She stared at me, and I shuddered inside. My mind swirled. Was she going to out me? Blackmail us? What was she planning for my wife?
This last thought stirred my cock in the cage as I returned home.
Source: reddit.com/r/eroticliterature/comments/jef8ar/sharing_old_bob_mf_femdom_pegging_sissification