Down the Rabbit Hole – Part One
Seduction of a young man by a cross dressing Dominatrix and turn into a sweet little girly boy.
Dennis St. John
This book entirely fictional and solely for adult entertainment as it contains graphic sex between m/m m/b, bondage, rape, taboo subjects, offensive words, and language, and generally ignores PC correctness, the rules of good behavior and good manners. Being duly warned, read on.
Copyright © 2020 by Dennis St. John. All rights reserved.
First Electronic Edition: April 2020
Growing up, I always thought of myself as a ‘normal’ young man, and apart from a few ‘kinky’ things I did with my school friend, jacking each other off, or letting him lay on my back and put his cock between my closed legs to pretend to fuck me, was about as far down the rabbit hole I was willing to go. Looking at my made up face in the mirror, powder blue eye shadow, thin black eye liner, blush on my cheeks and frosty pink color on my lips, I wondered how Aunty Jimmy was able to turn me into a pathetic little cock sucking sissy faggot so easily. My honey blond, shoulder length hair framed my face and hazel eyes in such a way as to emphasizing my sissy girlyboy look. It also made me look so weak and fuckable, as Aunty Jimmy would say, and earn me more money from my steady customers.
In a way, Aunty Jimmy was my Mommy, Mistress, and my pimp, taking care of me, making sure I was dressed and made up just right. He didn’t tolerate disobedient, pouting, attitude, or laziness, and I’d been over his lap more than once with my panties pulled down for a bare bottom spanking. In that regard, Aunty Jimmy didn’t play around with a punishment spanking, and smacked my bottom with a hair brush or paddle until I was crying. After that came corner time, and the most humiliating part of having to admit it was my fault and thanking him for the spanking me and correcting my behavior. I also had to show him how sorry I was for being bad in a very special way
Of course, that was all part of pushing me down the rabbit hole and stemmed from my childhood. Getting a spanking from my mother or father wasn’t unusual, more from my mother than father. Mom only spanked me with my pants on, whereas my Dad pulled both my pants and underwear down to administer the punishment to my bare bottom. I didn’t realize how sexual that was until later, especially having my skirt tucked up, and feeling Aunty Jimmy slowly pull my sissy pink panties down. In that regard, I suppose Aunty Jimmy was right, it was my fault I deserved to get a spanking as I had screwed up. Party it came out of me being somewhat submissive growing up, always doing what adults told me, never thinking to challenge them or say no. Even so, I still got into trouble, hence the spankings.
Getting a hard spanking from my father taught me the error of disobedience after I borrow his fishing rod without permission and broke it. For that spanking he made me strip naked before he pulled me over his lap. Thinking back, I realized he liked to spank my bare bottom and I often wondered if he jerked off thinking about molesting or fucking his son. Even though it was a shameful thought, for some reason it made me hard. That just played into me being submissive with older men who wanted me dressed in tweeny clothes so they could molest me. Quite often I’d get a spanking from my ‘Daddy’ as little girls and sissy boys should. Mostly those were just for play, but I did learn they loved to hear me squeal, whimper and beg them to stop. I could even manage a few tears to make it believable. There was something about having a kneeling sissy boy with tears running down his made up face, pouty pink lips wrapped around the shaft of his stiff cock and sucking their stiff cock that just drove men wild.
If it was short time, like one hour, I’d try to make them cum in my mouth, as most older guys couldn’t get it up again to fuck my boy pussy. If they rented me for the whole evening they got me on my knees sucking their hard cocks, and time to recover to fuck my boy cunt. Viagra is a wonderful drug for older guys, enabling them to do things now they couldn’t do when they were younger, like fucking the brains out of a submissive panty boy and pretend girl. At their age, touching anything under 18, or 21 was out of the question, but with my looks, small titties, make up and clothes, it was easy for them to believe they were molesting and fucking the most taboo and forbidden of all fruits, a pre-teen girl. Well, at least a convincing pretend one.
They paid well, giving it to Aunty Jimmy before the ‘date’, and many times leaving me a great tip. Jimmy was careful about the money, making sure my share, the bulk of the money, when into a saving account and giving me the book back after he’d made the deposit so I could see.
That was to cum, so to speak and my destiny. It started due to the deteriorating situation between my Mom and Dad after she caught him cheating the second time. Barely 15, she lied on the entrance form and said I was 16 so I could join the merchant navy. Being so young, the only ship I could get in the beginning were coastal freighter as an assistant steward. That meant I had to bunk with another person, something I’d never done before, except camping with the scouts, but then there were five or six in the tent. The senior steward was Jimmy, and it was his job to teach me what I had to do. How to lay the table for each meal and things like that. I did think he was effeminate, but it wasn’t until later I discovered he was a queer, something I’d only heard dirty joke about at school. Jimmy was a very handsome looking man, slim build, and a head taller than me. His eyes were gray/green eyes, with light brown hair which he kept in a pony tail while on duty.
It took a bit of getting used to, living with a man who wore lady’s panties all of the time, not that he did anything odd, except maybe made sure I was wearing a clean uniform, combed my hair and looked presentable. For the first time I had to make sure my nails were trimmed and clean, but I still had a bad habit of biting them when I was nervous. Of course, Jimmy had a cure for that. After filing and shaping my nails he coated them with clean nail polish. It tasted horrible, and I soon stopped biting them. We also talked a lot in the evening when he wasn’t off doing whatever queers do with one of the crew. I never asked him about it, even when I accidently saw him getting dressed without his slack on one evening before he went out. He was wearing thigh high stocking and a garter belt, girl’s panties, and a black lacy bra. I quickly backed out of the room, blushing like mad, hoped he hadn’t noticed me. It turned out he had, but he never mentioned it.
Six months later on the return trip we ran into some rough weather and I got sea sick. It was so bad, all I could do was lay there, moan and try to throw up. Jimmy looked after me and no one said anything about me not being on duty. Guess I wasn’t the only one sick. I still didn’t feel right even after we reached port in Southampton. I pulled on a pair of old jeans, shirt and jacket and went ashore to called my Mom and tell her I was home. That’s when I found out they’d split.
“I’m be staying with a friend, Robbie. Can’t you get another trip, or berth?”
“I don’t know, Mom. I’ll have to check in at the Union Hall.”
“Why don’t you do that, Robbie. I’m sure you can find something. As soon as I’m settled you can come and stay with me when you’re ashore.
“Yes, Mom. I can find something, maybe I can work ‘stand by’ or find a small place to rent.” That’s what a lot of seamen do between trips.
Jimmy could see I was upset, and almost on the verge of tears. Add to that still partly seasick it was the perfect opportunity to move in. I stuffed my few clothes into my small duffle bag and went ashore again, finding a taxi outside the main gate.
“Can you drop me of at the Y. I’ll get a room and go down to the Pool when I feel better.” Jimmy patted me on the shoulder.
“No, silly, you’re coming home with me. You need looking after until you’re well again. You can stay at my place as long as you like, or until you get another berth.” I was too sick to argue. My head ached and my tummy wouldn’t stop rumbling.
I don’t remember much of the trip except we ended up in Soho and a walk up flat on the third floor. Between getting there and being put to bed, I lost track of my suit case, but I didn’t know that until later. I remember falling into bed in just my underwear after Jimmy gave me a glass of warm milk, hearing Jimmy saying something about taking my dirty clothes to the laundry, but not much else until later the next day, still feeling a little fuzzy. I felt myself blushing as Jimmy came in wearing stocking, garter belt, panties, and a teddy under a silk robe. It was open and he didn’t seem to care if I saw what he was wearing or not.
“Time to get up and take a shower Robbie. Use the cream in the bottle first and leave it on for a couple of minutes while you wash. After that, wash it off and use my shampoo and conditioner.”
“Oh… okay.” The water on the ship wasn’t very good, and my hair did feel a little greasy so I didn’t think much about it.
“We’ll have breakfast after.”
Stripped off my underpants I climbed into the shower once the water was hot and followed his instruction. Jimmy came in and I could see him moving around on the other side of the plastic curtain.
“Use the pink soap and a buff pad, here.” His hand came around the end of the curtain holding a bunch of pink something. I took it, using both while I waited the two minutes for the cream to do whatever it did. The shampoo, conditioner and soap did smell good, lavender I think, but in my fuzzy condition I didn’t really care. Stepping out I wrapped a towel around my fiddle just as Jimmy came back in.
“Here, let me dry your hair for you.”
“That okay, I can manage…” I started to say, but Jimmy just tutted and grabbed a towel and started rubbing my hair after drying my back.
Despite my protests, in a way it felt good, rather like when my mother did it when I was younger so I stood still and let him do it. He wasn’t finished and insisted on brushing and combing my now shoulder length hair.
“We need to get you a haircut soon. Your hair is such a mess.” He came round in front of me to brush my hair down and trimmed it, and being that close I saw he had real breasts. I couldn’t help but look down, partly to make sure he was a man, and not a real female. He was wearing a pair of shorts like panties and I could see the bulge, so I knew he had a cock. He saw my blush.
“What?” He asked, smiling down at me.
“Um… nothing, I just…”
“Thought I was a woman because I have titties?”
“No, I’m male and what they call a transvestite, when they are being polite that is”
“Oh.. um.. I see.” I didn’t but wasn’t willing to admit that. I was so innocent then.
“What do they call you when they aren’t being polite?”
“Oh, they have lots of names. Pansy, poof, queer, faggot, bitch boy, sissy cunt and any other nasty name they can think of.”
“That’s not nice.” Jimmy laughed.
“At the right time it can be. Come.” It wasn’t until later I understood what he meant. We walked back into the bedroom and I looked around for my duffle bag and my underpants.
“Where is my duffle, Jimmy?”
“Your duffle… oh my.” He froze and looked at me, biting his lower lip. “We must have left it in the cab. I’m so sorry. I didn’t think.”
“What?” I asked.
“I didn’t think… thought you had had something else to wear,” Jimmy had the grace to blush. “ I… I also threw your old ratty underwear away. I stood there, blinking, wondering what I was going to do.
“Don’t worry, I’ll buy you some new clothes, promise.”
“W-what am I going to do in the mean time?”
“Um… well, you can wear a pair of mine. Go look in the top draw. There should be a packet of new ones at the back.” I felt my ears get read at the thought of having to wear a pair of real girl’s panties, but it was even worse than I thought. The packet of news ones were pink satin panties with frilly lace around the elastic legs and waist.
“Do you have anything else I can wear?” Shivering and blushing.
“No, I’m sorry. I haven’t wore men’s underwear for years,” he laughed, “stop being such a sissy and put them on.
Blushing furiously, I retreated to the bathroom and dropped the towel. My finger shook a little as I pulled out a pair and put them on. They felt so different to boy’s underwear, almost caressing my bottom and crotch in a way I’d never felt before. I felt myself starting to get a stiffy thinking how taboo and forbidden it was for boys to wear girl’s panties. I couldn’t help but squeeze my cock through the satin material. It felt good and I stood there looking at myself in the mirror. Before I could frame the thought about how I looked, Jimmy came in.
“Here, you can wear this until I buy you some knew clothes.” Jimmy held out something flimsy, pink, and sheer. “Hold your arms up.” Embarrassed at being caught with a stiffy, obediently I did, as Jimmy bunched whatever it was in his hand and slipped it over my arms.
Looking down, I found I was wearing something like a toga, open at the sides and a deep Vee down the front. I stood there shivering and blushing as he tied the pink ribbon together on each side.
“Can’t have you running around in just panties now, can we.” I shook my head, not daring to look him in the eye.
I suppose, if I’d wasn’t so fuzzy, I might have objected, but in my present state I accepted with only a little protest. The toga, or gown only came down to mid-thigh, but Jimmy’s flat was warm enough I didn’t feel cold. To finish off the outfit, he slipped a pair of thin, soft foot covers you see ballet dancers wear. Compared to what he was wearing, my outfit was positively plain. I think the fact he was dressed fem relaxed me as what I was wearing wasn’t out of place. After that he took me to the kitchen where we made breakfast. Me, scrambled eggs on toast and a cup of hot chocolate. I felt a little better after that, but still a little fuzzy.
That lasted a couple of days, and by that time I wasn’t so self-conscious about prancing around his flat in my outfit. I’d also gotten use to sleeping with Jimmy in his big bed, but other than a little cuddle he didn’t do anything else. One morning, after a shower, doing my hair and dressing, I found Jimmy searching through his coat pockets.
“Damn it! I know I put it in my pocket.”
“Your laundry ticket. I can’t get your clean clothes without it.”
“Oh.” I dawned on me I didn’t have any clothes except what I was wearing.
“Never mind. We’ll buy some nice new things, but from what I saw of them on the ship, they were no loss.”
“B-but how am I going to buy new clothes. I don’t have anything else to wear except this.” I spluttered.
“Oh, I can find a few things for you to wear out.”
“Can we go today?”
“No, it’s pouting with rain, and I have an early date this evening.”
“Oh.” Suddenly the prospect of being by myself the whole evening might not be so bad. It would give me a chance to play with myself. Ever since I started wearing these panties, I was semi hard all the time and there was a wet spot.
After lunch, Jimmy took off to take a shower and get ready for his date. I did wonder about it and what he did. Out of curiosity I poked my head into the bedroom, seeing Aunty Jimmy seated in front of his makeup mirror.
“Come in Bobbie, I’m dressed… well half dressed.” He laughed. He was, wearing a black and red corset, black stocking, black lace panties and his flowery robe. The six adjustable garter straps were part of the corset and gave it a very slutty look
“I know, but I like Bobbie much better.” I’d been called both so I didn’t mind.
I sat on a chair next to the vanity and watched intently and how he changed from a good-looking man into a sexy looking female. A 5’10” Aunty Jimmy topped most men when he wore his high heels and I wondered how tall the man she was going to see.
“Be a dear and get me my boots from the closet.” I did, surprised to find they were thigh high black boots with four inch spike heels. Shiny and soft to the touch. I returned to my seat and watched in fascination as he gradually transformed himself into a beautiful woman. I sat there grinning.
“What are you smiling about?”
“Nothing… well, it’s just how you, um… changed.”
“You mean from a man into a woman?”
“It’s easy really. I could make you look like a girl just as easy.”
“W-what, me? No way. One look and they’d know I was a boy.”
“Want to bet.”
“What do you mean.”
“Move the chair closer and I’ll show you.” I shifted my chair closer, feeling excited. “First a little base and some eye shadow. Close your eyes.” No sure what to expect I did, feeling him brush something on the cheeks, then my eye lids. “Keep your eyes closed while I do the eye liner.” I felt myself shiver, not knowing what to expect.
Standing he turned my chair before I could see myself, tilted my head back and applies lipstick after outlining my lips with something. Facing away from the mirror, I couldn’t see what was happening, so I just sat there and let him do whatever. Next he brushed and curled my hair, using a little hair spray to hold it in place.
“Right, that’s good. Just a little lip gloss to seal the lipstick in place. That way you won’t leave lipstick on the cups or glass.” I giggled softly hearing that. “Okay, you can look now.” I turned and froze in shock, seeing a young girl looking back at me.
“Oh no! I look like a girl.” I did, and I couldn’t see me, the boy, just a young teen girl looking back at me.
“You really need to get your eyebrows plucked and shaped to give you that young teen look.” Aunty Jimmy laughed. “With a proper outfit no one would even suspect you of being a boy.” I shuddered at the thought of being dressed in girl’s clothes as well. Then Aunty Jimmy reached round and squeezed my stiff cock through my panties and I realized how turn on I was. I let out a moan, biting my lower lip, now colored a soft pink.
“People will know I’m a boy…” Jimmy shook his head.
“People believe what they see and nothing else. Dressed and made up all they will see is a sweet teenage girl. Wouldn’t it be fun to be a girl for a day?”
“Nooo, it would be humiliating.” I blushed, adding more color to my soft cheeks.
“Keep the makeup on for tonight and enjoy yourself.” I wasn’t sure what Jimmy meant by that until later. “Go make yourself some hot chocolate while I finished getting dressed. Suddenly I felt very naughty and scampered away to do what he said, looking at myself in every mirror surface and glass door.
Aunty Jimmy came out a little while later while I sat curled up on the couch sipping my hot drink. My eyes opened wide seeing him, now dressed in his high heels leather boot, leather mini skirt and black half jacket. I could see the black and red corset under the open front of the jacket and the garter straps between his mini skirt and boot tops.
“You like?” He asked, spinning around.
“Y-yes.” I gulped. “You look terrific.”
“I hope my dates likes it as well and appreciated the effort that went into my Mistress look.”
“Yes, Bobbie, I’m a Dominatrix, a Mistress if you will and some men love me humiliating and spanking them for being bad boys. They are so obedient after I’ve punished them.” I gulped as visions of someone getting a spanking for him flashed through my brain.
“Make sure you wash up the dirty dishes and tidy up the kitchen before you go to bed, or you’ll be over my lap getting a spanking as well.” Jimmy said it with a smile so I didn’t take it seriously. I should have done. Slipping on a long rain coat, Jimmy covered me with a blanker and gave me a kiss on the cheek.
“Watch TV, but don’t stay up too late.”
“I won’t.” My hand already sliding down to squeeze my cock under the blanket.
I lay there after he’d left only half watching the TV, more interested in touching myself through the satin panties and thinking about what he’d said. I tried to imagine what I’d look like and how I would feel being dressed up in teen clothes and walking down the street like that. It felt so wonderfully shameful fooling everyone into thinking I was a girl. I lay with my eyes closed, hand inside my panties thinking about jerking myself off. Instead the hot chocolate made me sleepy. The next thing I knew was Aunty Jimmy shaking me awake. Opening my eyes, I blushed as he pulled the blanket off and caught me with my hand still inside my panties.
“You’re such a naughty boy doing that. Your pretty panties will get dirty.” Taking my hand, he pulled me off the couch and into the bedroom, still dressed in his outfit, including the boots, minus his overcoat and jacket. He let go and walked over the get the chair and a hair brush set the chair it in the middle of the floor.
“Come here, Bobbie. He snapped. Shaking, I walked over and he stood me beside the chair as he sat, pulling his leather skirt up as he did. Still half asleep I didn’t realize what he was going to do until he pulled me down over his lap.
“Jimmy… please no.” I knew then he was going to spank me.
“What did I tell you to do before I went out?” He demanded. I had to think.
“Y-you told me to wash up the dishes and tidy the kitchen.” I sobbed.
“Did you do it?”
“No.” I said between sobs.
“I told you what would happen if you disobeyed, didn’t I?”
“Y-yes… but.. I fell asleep.”
“I’m not interested in excuses, Bobbie. I told you to do something and you didn’t do it, did you.”
“Then whose fault it is you are getting this spanking.” As he spoke, Jimmy lifted the hem of the toga to expose my panty covered bottom. “Boy’s like you have to learn to behave themselves and do what they are told, don’t they?”
“That’s yes, Mistress.”
“Yes… Mistress.” I felt him hook his thumb under the waist band and slowly work my panties down to expose my bottom. I let out a soft squeal of protest.
“Please… don’t spank me!” He wasn’t listening.
“Now then, who fault is it you are getting this spanking?” He asked as he ran his hand over my bottom. This was worse than when my mother or father spanked me and I started crying. Just like my mother, he was getting me to admit what I’d done and whose fault it was.
“Good. You will lay there like a good little boy and take your punishment.” Anticipating I’d start kicking, he hooked on leg over both of mind and wrapped his arm around my waist. He started spanking me with the hair brush, not hard at first just to warm my bottom.
“Whose fault it is, Bobbie?”
“Mine.” I sobbed and he started spanking me harder.
It hurt a lot more than when my Dad spanked me and I felt so ashamed and humiliated to be getting a spanking at my age. Suddenly I wasn’t 16 anymore but a little boy again getting a punishment spanking for being naughty. I squealed and whimper, begging him to stop but he didn’t. Then I started struggling, trying to get away from the horrible hair brush slowly turning my bottom into a pulsing hot mass of pain that radiated down my thighs. It was no use. I wanted to scream, but knew that would only make his spank me harder so I clamped my hand over my mouth.
“Are you going to be disobedient again my little Bobbie.”
“N-no Mistress, I won’t I promise.” I sobbed, hoping he’d stop.
“Good, from now on you do what you’re told, or else. Do you understand?”
“Y-yes, Mistress.” After a few more hard smacks to remind me, he stopped and lifted me up. I stood there shifting from foot to foot and trying to rub my stinging bottom.
“Now go stand in the corner until I tell you. No, leave the panties down and put your hands on top of your head.” With my panties around my thighs I could only shuffle over to stand in the corner, hands on my head, hot shameful tears rolling down my face.
I never felt so humiliated in my life until then, and I couldn’t stop crying. Aunty Jimmy was right, it was my fault. I hadn’t cleared up the kitchen as he’d told me so I only had myself to blame for the punishment. I was slowly beginning to understand what Dominatrix meant and wondered how a grown man felt getting an over the knee, bare bottom spanking from a crossdressing Mistress. Any thought I had about being an adult fled as I stood there shifting back and forth from foot to foot to try and relieve the throbbing pain in my bottom. I was a little boy again being punished by my mother. I heard Aunty Jimmy moving around behind me, not daring to look for fear of another spanking.
“Come here Bobbie.” Turning I started to pull up my panties. “Leave them were they are.” His stern look said it all, and I did what I was told. I shuffled over, hands over my cock, and to my surprise he took me in his arms and hugged me.
“I didn’t want to spank you, Bobbie, but you were disobedient, weren’t you?”
“Y-yes… Mistress.” I sobbed, fresh tears running down my face.
“So, are you going to behave yourself in the futured and do what you’re told?”
“Yes, Mistress. I will, I promise.” He stoked my hair and made soothing sounds.
“Good. You behave and I won’t have to spank you, will I?”
“No, Mistress. I’ll be good.” Reaching down he pulled my panties up, careful not to scrape the waist band over my tender bottom.
“It’s late. Let’s go to bed.”
I nodded and wiped my tears away, feeling a little better. Before getting into bed, he switched off all but one of the light in the bathroom so we wouldn’t stumble around in the dark if we needed to go for a pee in the middle of the light. I was just getting comfortable on my side, feeling dejected and lonely, still sobbing a little.
“Come here, Bobbie.”
I rolled over and looked at him and saw he’d changed into a sheer black night gown, laying there with his arms open. I quickly moved over and he gathered me into his arms, holding me tight, my cheek against his lovely breasts.
“Is that better, Bobbie?”
“Yes, Mistress.” I murmured looking up and to my surprise, he leaned down to give me a soft kiss on my lips. I shivered and let out a sigh. At that moment he wasn’t a man but a female and ‘she’d’ just kissed me in a loving way. I returned in, but he draw back and looked me in the eyes.
“Are you sure you want to kiss me, Bobbie?”
“Yes, Mistress, I do.” And I did, never really having kiss a girl before.
I wasn’t sure how to kiss really, but Jimmy showed me, opening his mouth slightly to kiss me again. I did the same and it wasn’t long before his tongue was probing my mouth. I moaned, feeling myself start to get hard. I did the same, and he let me explore the inside of his mouth, but it wasn’t long before his tongue was back inside my mouth, possessing it as if he own it. Our bodies came together and we began rubbing against each other, my little stiff panties cock rubbing against his stiff cock. He knew I was close to cumming in my panties, without even touching myself and pulling back, Jimmy smiled down at me, stroking and kissing my face all over.
“Have you ever played with another boy, Bobbie?” I felt my face get hot and nodded. “Tell me what you did?”
“W-we just touched and jerked each other cocks.”
“Did you ever suck his, or him yours?”
“N-no, we never did. Neither of us thought about doing that.”
“What else did you do?” I buried my face in his shoulder, to ashamed to admit what we did. Jimmy stroked the back of my neck and ran his hand down my back to stroked and caress my sore bottom.
“Come on, tell Aunty Jimmy what you did. It’s okay, I’ll understand.”
“W-we use to go up into the woods and undress. We’d cuddle and kiss for a while and touch each other.” I stopped, my face feeling hot. “Malcomb like to put cream between my legs. He’d lay on my back and push his cock between my thighs and pretend he was umm… having sex with me.”
“Say fucking Bobbie.” I gulped.
“He’d pretend he was fucking me… like I was a girl or something.” Jimmy laughed softly.
“Did you like that?”
“Not at first, but it did feel sort of good.”
“Did he ever try to put his cock inside you?” I shivered. “Whisper it to me.”
“Y-yes, a couple of time when he got excited, he’d miss and try to slip it into my bum. It hurt a little and I told him to stop.” Jimmy’s hand slipped down between our bodies and started to squeeze my stiff cock through my panties.
“Naughty Bobbi, you have a big wet spot in your panties.” I moaned and my hips started moving. “Did you like him laying on top of you?”
“Y-yes, it felt good him hugging me and moving his hips.”
“Did you want him to put his cock in your virgin boy pussy.” I let out a gasp hearing that, feeling my cock spasm.
“Sometimes.” I whispered.
“Do you like my titties, Bobbie?” I nodded. I’d seen my mother in her lingerie and robe and wondered what he breast were like without the bra. Jimmy pulled his night gown open. “Suck my nipples, Bobbie. Gently and run your tongue over and around it.” I moaned softly and did what he told me, putting my lips around the hard/soft nipple. Jimmy let out a long sigh.
“That’s a good boy, now bite it gently. Not too hard.” I did and Jimmy let out a long moan and put his hand on the back of my head to push my face against his breast. Holding my head by my hair he moved my mouth to the other one and I did the same.
“Lay back, Bobbie. I’ve going to do something nice for you.” I rolled onto my back wondering what he was going to do.
Jimmy turned around as he pulled the bed covers back, stoking my body, chest, tummy and finally my stiff, panty covered cock. I shivered as he pulled my panties down and took hold of it, stoking me gently. Without warning I felt him lean over and take it in his mouth. I let out a soft whimper. It was nothing like I’d ever felt before and I couldn’t help my hips wiggling. Jimmy was an expert, and each time I came close to cumming, he’d stop and squeeze the base of my cock, holding it until I’d calmed down before starting again. I was lost on a soft pink cloud of erotic ecstasy, unable to think of anything else but the feeling in my cock. I reached out and touched the hardness I saw inside his panties, wanting to see it, feel it.
“Jimmy! I want to suck your cock.” I panted, and I did, wanting to feel it in my mouth and suck it like he was sucking mine.
“You’re not ready, baby. When you’re ready you can.” At last he stopped.
“Would you like me to do what Malcomb did, Bobbie?” I hardly knew what I was doing, remembering Malcom’s cock sliding between my legs. It made me feel so wonderfully dirty in some ways, knowing we shouldn’t be doing this, laying naked on the leaves with him on top of me, pretending to fuck me as if I were a girl.
“Y-yes.” I moaned.”
“Roll over onto your tummy.” I did, and Jimmy stripped off my now wet panties. He took something from the draw in the bed side table, and a moment later felt something cool run down between the cheeks of my bottom.
“Lift up, I need to put a towel under you.” I did, and Jimmy placed a small towel under my cock. He moved, straddling my body and I felt the tip of his cock touch the back of my thighs.
Jimmy moaned as he pushed his big cock between my tightly closed legs. I let out a gasp as the head slipped over my balls. Malcomb wasn’t big and I’d never felt that before. Shivering, I wonder how big Jimmy’s cock was, guessing it had to be six inches or bigger. Jimmy lowered his body onto mine and held me tight in his arms.
“That feel good, Bobbie?”
“Like a little girl getting her fist real cock, or a sissy boy getting his Daddy’s big dick for the first time.” I shuddered at the dirty thought of my Dad fucking me.
“L-like a little girl getting her first fucking!” I moaned, my hips bucking up to his thrusts, feeling hot saying that.
“Oh yes, a naughty little tweeny girl taking her big hard Daddy cock for the first time.” He whispered in my ear.
“Ohhh no Daddy, please don’t put your big hard Daddy cock in my little pussy, it so big… it won’t fit.”
“That’s better.” He whispered. “But that’s what happened to naughty little girl.” I shuddered unable to think, just react to his words. “You’re a naughty little girl, aren’t you Bobbie.”
“Y-yes, I am a very naughty girl.” Jimmy held me tight as he lifted his hips. I squealed as I felt the head of his cock push into my bottom between my cheeks.
“Jimmy… no… please.”
“Shush baby girl, just let me put the head in.”
“No, please, it’ll hurt.” I moaned as I felt the tip push into my ring, slowly forcing it open, but it didn’t hurt as much as I thought.”
“Just relax and let it slid in and out.” I started crying, whimpering, and wiggling my bottom to try and get it out. I couldn’t.
Jimmy moved the head of his cock in and out of my butt, and gradually the pain lessened. “There, that’s much better. Lift your hips a little so I can get the head in a little more.” Whimpering I obeyed, hoping it would be over sooner. Jimmy began moving his hips, slipping the head in and out, and as he said, my ring relaxed and the sharp pain stopped.
“There, see, feels better now, doesn’t it?”
“Y-yes… but please, don’t put it all the way in… it’s so big.” I sobbed.
“I know baby, it always feels that way at first.” Jimmy lied, as gradually his pumped his big hard cock all the way in until he was laying on top of me again.
“Oooo you promised.” I sobbed.
“I know baby, but you have such a nice virgin boy pussy, I couldn’t help it.”
“Please stop.” I begged.
“No, baby, you need this. Relaxed and enjoy it.” I desperately wanted to say no, I wasn’t enjoying it. But, it was a lie. It was starting to feel good, sobbing and crying, I started bucking my hips up.
“Please… not all of tiiiiii!” I felt his last thrust and knew he had his big stiff cock all the way inside my boy pussy, as he called it. “Ooooo noooo!” I moaned.
“Yes, that’s it, little sissy Bobbie like it, don’t you?” I shook my head, not daring to answer, but Jimmy knew. “Tell me the truth or I’ll spank you again.”
“Good boy.” He began pumping his cock in and out faster, sending waves of dirty erotic pleasure pulsing through me body.
“Oh god!” I moaned.
“That’s it. You’re a good little bitch now, aren’t you?” He was right as I wiggled and bucked under him.
“Please… stopppp.” I begged, sobbing in shame. He was fucking me like a girl, and even as painful as it was, it felt good as waves of erotic forbidden pleasure swept through me. Panting for breath, I lifted my bottom so he could get in easier, and gradually the pain eased.
“Oh yes, the little sissy girlyboy likes it. Don’t you Bobbie baby.” He whispered in my ear. “Tell me the true.” Even though I shook my head I knew it was a lie. It felt good.
“Yessss.” I sobbed as he slowly pulled out.
“You need to be on your knee, sissy baby so I can’t fuck you properly like a little bitch. Come on, on your knees.” He didn’t give me a choice as he lifted my hips and put me on my knees. I let out another sob as I could now see myself in the mirror along the head of the bed.
Jimmy put one arm around my waist to hold me in position while his other hand directed the head of his cock back into my boy pussy. I gasped, wanting it, and not wanting it. The head slipped inside with only a little pain and I knew I couldn’t stop him fucking me. Now I felt both hand holding my hips and his cock working its way deep inside me. I felt every inch slowly work its way inside as his hips bucked. He wasn’t gentle this time, panting hard and he fucking his way inside me.
“Fuck yes, now the little sissy bitch is getting the fucking Malcomb should have given him, or his nasty Daddy who liked to spank his little boy naked.”
“Please… not all the way.”
“What a little liar you are, you know you want all of my nine inch cock inside you, fucking you like a little girl.” I shuddered at the thought, but he was right, I did want it all the way inside me, despite the pain, realizing now this is what I wanted Malcomb to do all the time but never did.
I saw myself in the dim light, on my hands and knees, dressed in a sissy pink gown and made up face. Suddenly I was a little girl getting her first cock and I started wiggling my hips and pushing back.
“That’s a good little bitch, show your Mistress how much you like her big hard clitty inside you tight, virgin boy cunt.”
“Ooooo yesss… fuck me, fuck me hard.” I blubbered, shame washing over me. I was a dirty little sissy bitch now. Jimmy kept pounding into me, groaning with pleasure.
“Yesss, going to get you all dressed up in a sweet little dress and turn you into a proper little sissy bitch boy.” I almost shot my load hearing that, images of myself dressed as a little girl, prancing around, getting fucked and even sucking his cock.
It couldn’t last, and just as I was about to explode, Jimmy gave one last thrust to get his cock in as deep as possible before he filled me with his juice. For the first time in my life and came without even touching myself, shooting ribbons of cum all over the towel. Jimmy held it there until the spasms of pleasure passed, feeling the blood pounded through my veins like fire and ice at the same time. Pulling out, Jimmy rolled off to his side of the bed and let out a long sigh.
“I wanted to fuck you so badly the first time I saw you in your boy’s underwear.”
“You did?” I shivered at the thought.
“Oh yes, I wanted to bend you over, rip off your underwear and rape you.”
“Why didn’t you?”
“Because I knew you weren’t ready, and I was willing to wait until the right time and you knew you were a sissy queer boy.”
“I never… I didn’t.”
“Most boys don’t know how queer they are. It just a matter of getting them into girl’s panties first and letting nature takes its course. Now go to sleep my sissy.” Jimmy pull the covers over us and cuddled me. Even being call a sissy felt good.
“Are you really going to put me in a girl’s dress.” I held my breath.
“Well, you said you wanted to be a girl for a day, so yes. Tomorrow I’ll take you shopping, get you hair and makeup done and find you something nice to wear, alright?” I shivered at the thought of going out in the street dressed like a girl, and even though I wasn’t hard, it gave me a thrill.
“Okay.” I whispered. Jimmy kiss my neck.
“That’s good. Now go to sleep.”
“Am I your sissy boy now, Aunty Jimmy?”
“Yes, my sweet little virgin sissy girly boy.” That made me feel warm and comfortable, something I hadn’t felt for a long time.
END PART ONE
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#Reluctance #Teen #Virgin