Blackmailed

My name is Aden, a shy, thin, 5 foot 8 inch, s*******n year old, average looking, dark haired, self-conscious high school student. I’ve never dated and have few friends. My social unease is significantly due to the fact that my penis is unusually small. Erect it is only two and half inches in length and very slim in circumference. It is uncircumcised and when flaccid it shrivels up to such a tiny size it appears to retract into my body.

The last couple of years our parents have travelled half the week for business and are usually gone weekends. Our aunt lives an hour away and comes by only in an emergency. Due to what my parents call my s****r’s maturity she is left in charge in their absence and I’m required to obey her although she is only 14 months older than I am.

My s****r, Sloane, is 5 feet 4 inches tall, 105 pounds and very cute. We both have short pixie haircuts with bangs and both of us have dark brunette hair with natural sheen. And we’re both blessed with clear healthy complexions. She also has an athletic, appealing shape with a really nice ass and medium size pointy breasts with prominent nipples. When she wears a tee-shirt without a bra her nipples are really noticeable.

She has an engaging outgoing personality and everyone likes her. In public she plays down her intelligence and assertiveness. But when it comes to interacting with me she has always been the dominate one. I’m naturally passive and she is a take charge kind of person. When you factor in our age difference and my insecurities it’s not surprising that I follow her lead.

A year ago my life changed forever when my s****r caught me in her bedroom. I was lying on her bed and had a pair of her dirty panties covering my face inhaling her scent with my jeans and underwear around my ankles. My fingers were furiously stroking my full two and a half inches and I was so totally lost in masturbatory fantasies I never heard her. I thought the house was empty and she was at an outing.

My first awareness of my s****r’s presence was a succession of bright flashes. I immediately tore her underpants from my face and froze for a second before I franticly tried to pull my pants up. Continuing to snap pictures Sloane yelled, “Don’t you dear touch those pants”, which was said with such authority I obeyed.

I tried to put my legs together to hide my humiliatingly small cock from my domineering s****r but she said, “Unless you want everyone to know what a tiny thing you have, you better spread those legs, asshole”!

With total shame I opened my legs, exposing my inadequate little penis to my s****r. Although I was embarrassed and overcome with emotion, I instinctively knew it wouldn’t help to get the camera away from her. She would have just told everyone what she caught me doing and what a pathetically tiny penis I have.

Thoroughly defeated I let my s****r take picture after picture. She calmly stated, “Aden, if you do exactly as I say everything will be OK!”

Snapping away she ordered me to take the rest of my clothes off and stand up. Nervously I removed all my clothes and got up.

Standing naked I looked at the floor too humiliated to look at my s****r. She left me standing there with my arms awkwardly at my side while she took photos of my penis which had completely retracted. Finally she ordered me to pick up her panties from the bed.

As I stood holding her panties she instructed me to look at her and as I did she f***ed me to smile while she photographed me. She circled me taking photos from every angle and then she stood aside me rubbing her breasts against my arm and shocked me by cupping my small balls and begun to fondle them and in a sexy voice she said, “Aden, I’m going to help you get hard again and when you do I want you to jerk off and catch your cum with my panties.”

She then put her tongue in my ear continuing to gently massage my balls.

My teen dick responded and I stood with my small hard-on while my s****r stepped back and continued to take photos from every angle as I rapidly stroked my hard penis. And at the height of my arousal she said, “Alright now cum in my panties!”

And that’s exactly what I did. I shot out a thick milky load onto my s****r’s panties while she caught it all with her 12 pixel digital camera. As the cum was still oozing out my shrinking cock, in a sweet voice she said, “All right, I’m proud of you,
now give me a nice big smile,” so I stood smiling as she took her final pictures.

Sloane’s demeanour abruptly changed and she told to get out of her room. I begun to dress but she told me to just pick up my clothes and leave. So I dropped her panties on the floor and clumsily walked to the door with my clothes in my arms aware that she was still snapping pictures of my rear as I left.

My s****r followed me out of the bedroom and then continued out the front door. Almost as soon as she left I knew it was a big mistake to have allowed those photos, later when she came home I went to her room to plead for the SD card with the photos on them.

My s****r informed me she planned to keep the photos. She also stated that she had made multiple copies. She then gave me a flash drive with all the photos on it and told me to look them over. I was dismissed and she said she would talk to me the following day about the matter.

I went to my room and looked at more than a hundred photos in 12 megapixels, and every one of them was crystal clear. I was mortified that they existed and terrified that my s****r might show them to someone.

The next afternoon before my parents got home Sloane summoned me to her room to talk. She informed me that from that point forward I would be required to follow her orders unconditionally. And if I didn’t agree to her terms she would let all her friends in our high school see my nude photos. My s****r could be very mean so to avoid public humiliation I agreed to follow her orders.

The first weeks she would just have me clean her room in the nude and sometimes especially if she thought I was being disrespectful she would say “show asshole” and I was required to turn my back to her and bend over and spread my ass cheeks wide showing her my asshole. I had to hold the pose for as long as she wanted. It was humiliating to be so totally exposed but I was afraid of what she would do if I defied her. As time passed I was required to clean our entire home, usually naked.

Periodically Sloane would require me to stand and masturbate and while I did she would ridicule me for what she called my “small package” telling me constantly I would never be able to satisfy a woman.

Along about the third week she informed me that privacy was something I was no longer entitled to. She said, “From now on unless our parents are home you will keep your bedroom and the bathroom door open at all times.”

Since then, when I’m in the bathroom if she needs to speak to me or just wants to cause me embarrassment she will enter, especially if I’m using the toilet.

She also requires me to sl**p in the nude without bed covers with my bedroom door open. Additionally my s****r for the last year has required me to keep my legs separated while I’m in her presence whether I have clothes on or not. This means if I’m at school or anywhere else and my s****r is present I must keep my legs open. I am not allowed to cross them. I don’t have to keep them obscenely open, just separated.

Along about this time Sloane ratcheted things up again when she informed me that I would start pleasing her with my mouth. Beginning on her asshole and then on her pussy when she deemed me ready. She also told me at least initially I would have to be blindfolded and she immediately placed a blindfold on me.

My s****r laid out the ground rules that I would have to follow. She made it clear that I was there for her pleasure and not mine. I was told that I wasn’t allowed to use my hands on her for my satisfaction. I was only to use my hands to position myself while she laid face down on her bed with her legs spread wide. I could use my hands to locate her legs and once between her legs I could use my hands to spread her ass cheeks wide and no more. And my mouth would have to stay on or in her ass. My s****r made it clear that if I disobeyed her that there would be severe consequences.

That first day I had real reservations as I positioned myself and blindly touched my naked s****r for the first time. I put my hands on her ass cheeks and spread them wide. Sloane told me I could start slowly by kissing and licking her ass cheeks but I was frozen and was unable to start and that’s when she said, “Hey needle dick, you better start kissing my ass if you know what’s good for you.”

So the first time I ever kissed a girl in any way, it was on my s****r’s naked ass. And in a truly smug way she said, “Needle dick, you better get used to kissing my ass!”

So I spent the next few minutes kissing her ass all over but was interrupted when with obvious annoyance she said, “Start using your tongue,” so I begun licking her ass cheeks which caused her to relax and moan.

Hearing her moan gave me the nerve to put my tongue in her ass crack. She seemed to really like that and told me to lick up and down which I did and then she told me to put my tongue directly on her asshole. I took a deep breath and buried my nose between her ass cheeks, my tongue touched her asshole and she went wild, she had me put my tongue in her asshole as deep as I could and being the wimp I am that’s what I did. And for the next 35 minutes as my hands and mouth got very tired I slurped, sucked, licked and fucked my s****r’s asshole with my tongue. And sticking my tongue up my s****r’s asshole became something that became routine for me.

In front of her friends she began calling me “little guy” and “little man” much to my dismay. I pleaded with her not to but she wouldn’t stop. I was already insecure and my unease increased as she became bolder and more open with her ridicule of me. I was concerned that with her constant reference to me as “little” people would begin to guess at her inference, which some did.

Each day after school when my s****r was home I was f***ed to strip naked and lick her asshole. Yet I never saw her nude because she kept me blindfolded when she had her clothes off. Then one day as I prepared to lick my s****r’s asshole yet again she rolled over and told me it was time to learn to ‘eat pussy’.

The rules for using my mouth on her vagina were that I was not to use my hands to explore. I was only allowed to use my mouth, my s****r would lay on her back with her legs spread sometimes using her hands to spread her pussy lips open. She was sometimes quiet sometimes moaning and often, especially in the beginning she gave directions, telling me where and how to lick, suck, lap and kiss her “pussy”. She constantly berated me for having a “needle dick”. She would say things like “b*****r, with that puny little dick of yours you better learn to use your mouth. What woman would allow you to put that tiny thing in them? How would they even know you had it in?”

At times Sloane would have me stand before her nude and require me to achieve an erection without touching my genitals. She would tell me what to think of while I tried to get and keep an erection as I “performed” for her. The constant theme was always some kind of private or public humiliation or embarrassment that I had to imagine to endure either at her hands or someone else’s. She would sit in a comfortable chair while I “performed”. I usually shut my eyes while I thought of the fantasy she presented.

I think she knew my lack of confidence and general passivity would make it much more likely that I would find the scenarios she laid out sexually arousing. Her constant belittling of me only served to reinf***e my low self image. And her fantasy scenarios and degrading treatment of me only served to reinf***e my association of sexual arousal with her themes of humiliation.

Sometimes she would just sit and laugh at what she called my ‘sorry excuse for a hard-on’. If I lost the erection because of her ridicule she would f***e me to bend over and submit to a strapping until my ass turned red and then she would have me stand in a corner with my red ass on display. And she would say things like, “Since you have a little boy’s penis I’ll treat you like a little boy!”

When I was able to get an erection I was required to ask permission to leave the corner and show her my hard dick, if she was satisfied with it’s firmness I would be allowed to leave the corner, otherwise I would have to stay there until I was able to achieve a hard-on without using my hands for stimulation.

After two months I was so accustomed to the mockery that it didn’t really bother me that much. I kind of liked the attention but that changed on a Monday when Sloane told me the following Saturday she was going to have her best friend Megan and Megan’s boyfriend Jess over and she let me know that I would be the entertainment.

I pleaded and pleaded with my s****r all week not to embarrass me by having her friends involved in humiliating me but she was adamant. She told me that since she had shown Megan a few photos of me nude, smiling and sporting ‘a little hard on, Megan really wanted to visit while I was being ‘trained’. And my s****r made it clear to me that Jess was being invited because Megan told her he was really hung. Sloane felt that the contrast in size between the well hung Jess and me would be a good lesson for me. The thought of comparing my cock to Jess’s didn’t sound like much fun to me but my s****r wouldn’t change her mind.

I spent the week terrified of what would happen Saturday. During the week I bumped into Megan in school and I couldn’t make eye contact with her knowing she had seen photos of me nude. She would say, “Hi, Aden” and all I could do was look away and blush.

Thursday Sloane was waiting for me in the living room and she told me to take my clothes off right there. I asked her if we could go upstairs but she insisted that I strip right there. I followed orders and she watched as I took everything off. When I was standing nude she told me, “Sit down, spread your legs and play with your little dick but don’t cum!”

So I sat and fondled my penis while my s****r fully dress watched me. “Aden I’m going to run by a few things about this coming Saturday. As you know I don’t mind embarrassing you but I won’t allow you to embarrass me in front of my friends. Saturday you will follow my orders without complaint and if you don’t you will be very sorry!” Sloane continued, “Do you understand me?”

As I continued to fondle my penis I told her, “I understand, Sloane.”

“Good go clean the bathroom and do it with a hard-on!”

I responded, “Yes, Sloane!”

Saturday afternoon came and Sloane had me wear clothes because Jess and Megan were coming but rather than my usual underwear she had me wear a pair of her low rise pink panties. She had me model them for her insisting I pull them up so they fit really tight. She preferred that I wear them tight because she said, “Little Guy, you look so cute in these and I love that you don’t show a bulge like most guys would!”

Around 4PM I heard Megan and Jess in the living room and after a brief time Sloane summoned me by calling out, “Hey little guy, its show time, come in here!”

I didn’t dare hesitate so I just walked into the living room, very nervous, blushing and unable to make eye contact with anyone.

Sloane was sitting in the recliner and Megan and Jess were sitting on the couch. Sloane told me to come stand in front of the couch which I did and she said,”Aden as you know I’ve shown Megan photos of you naked and she thinks I’ve doctored them and she doesn’t believe your penis could possibly be as small as it looks in the photos. And she doesn’t believe that you give me unquestioned obedience!”

Sloane continued, “Aden I will ask you two questions and I want an honest answer each time. First what size is your erect penis”?

Looking at the floor I quietly said “Two and half inches.”

“And will you follow any command I give you tonight?”

“Yes I will!”

“Ok strip down to your underwear,” my s****r ordered.

I took my sneakers off and then my socks then my jersey and my jeans came off next. I stood very awkwardly with my s****r’s very tight pink panties making me feel vulnerable and effeminate. Both Megan and Jess were chuckling and Megan pointing at my crotch said, “Jesus Christ there’s no bulge at all. Aden, you look like a little girl.”

Sloane said, “Little guy it’s time to show our guests what you’ve got between your legs. Slowly pull your panties down and while you do I want you to look into Megan’s and Jess’s eyes. You’ve been very rude by looking at the floor the whole time. Do you understand me?”

Blushing profusely I said, “I understand Sloane” as I started to slowly lower the panties looking right at Megan and Jess.

Their eyes were mostly glued to my crotch with only quick glances at my face.

I was a very shy sixteen year-old boy who up to that point had avoided gym class or public restrooms for fear that my secret of a dreadfully undersized penis would be discovered. And here I was about to expose myself to one of the prettiest girls in my school and a boy who was widely regarded as the school stud.

My genitals had the same look and feel as if I had just stepped out of freezing cold water. My penis was completely shrivelled in size from embarrassment and my balls were tight and shrunk from fear as I lowered my s****r’s panties. Megan and Jess both gasped in surprise and Jess said, “Wow, you are so tiny!”.

I stepped out of the panties and stood rigid with my hands at my side trembling while Jess and Megan stared at my genital area. I was never more humiliated in my life as I stood totally exposed and on display.

Sloane told me to go stand directly in front of Megan so she could examine me. I stood in front of her while my dick was at her eye level. Although I was embarrassed I could feel my penis stir and an erection coming and soon my penis was rock hard at its full two and half inches. Megan reached up and cupped my balls which caused my penis to pulsate and visibly throb. She asked me in a matter of fact way, “Aden do you realize how small you are compared to other boys”?

With her hand still on my balls I said, “Yes Megan, I know”.

And then she said something that stung even more as she massaged my balls and studied my hard-on, “Aden, I don’t think many girls would want a guy with such a small cock”.

I don’t know if her comments were just thoughtless or meant to be cruel and mocking but in either case they hurt.

Sloane ordered me to turn around and show her guests my ass. I turned and after a very long pause my s****r said, “Show asshole!”

I bent at the waist, reached back and spread my ass cheeks wide for inspection just as my s****r had taught me.

Still bent over with my hairless boyish asshole clearly visible to Megan and Jess my s****r asked me a series of questions which I answered which included my acknowledgement that at my s****r’s direction I would clean, do errands, lick asshole, eat pussy or give blow jobs. After each question I would have to say, “Yes I will clean! Yes I will do errands! Yes I will lick asshole! and etc.”

When it got to the part about sucking dick I paused for just a moment before very quietly saying, “Yes, I will suck dick”.

Then Sloane just to embarrass me further asked “And you will swallow semen?”

Defeated I quietly said, “Yes, I will swallow semen!”

Megan touched Jess’s thigh and said, “What do you say I’ll love to see the little guy take care of you, what do you think?”

Jess said, “Let’s do it!”

My s****r said, “Let’s all go upstairs to my bedroom, and to me she said, “Needle Dick, you lead the way so we can watch your naked ass!”

I walked up the stairs very aware Megan and my s****r would soon be watching me orally please Jess.

When we got to Sloane’s room Jess didn’t need any prompting to get naked. He quickly took his clothes off while looking at me and my s****r to see our reactions. He was obviously proud of his body and especially his cock. He massaged his large low hanging balls and pulled his dick and it and it quickly got to at least eight inches and it wasn’t even completely hard. He was clearly full of himself but what he hadn’t understood was that Sloane intended to direct the action.

Sloane told him that if he wanted me to lick his asshole to lay face down and spread his legs which he quickly did. And to my complete shame my s****r had me get in position to lick his asshole, as she and Megan prepared to watch.

Sloane then told me to part Jess’s ass cheeks and start using my mouth. I did as I was told and for the first time was able to see an asshole which I was about to put my mouth on. Jess’s behind was clean and a bit hairy with a flesh coloured hole. I looked
over to see both Megan and Sloane watching intently, the fact that I was being f***ed to perform without any reciprocal sexual attention whatsoever was just as demeaning as my s****r intended it to be.

But as I lowered my mouth to the boy’s ass I just tried to please him. I slurped, sucked, kissed and penetrated Jess’s asshole with my tongue. My tongue was so far in Jess’s asshole that my nose was completely in his ass crack.

Jess was moaning with pleasure and he begun to rise up off his stomach so he was on his knees with his head down on the bed. This meant I had to rise up on my knees as I licked his asshole. This position made it possible for the girls to see all the action and as bad as my embarrassment was it got worst when I had to kneel with my face buried in Jess’s ass.

I couldn’t hide my erection from the girls and it was embarrassing to me that girls thought I was getting off on licking a boy’s asshole. Well if I’m honest I was partly aroused from trying to please Jess but mostly I had an erection because I found it sexually exciting to be watched by the girls as I pleased a boy with my tongue.

It seemed that Jess would have been content to let me worship his asshole all afternoon. It was obvious that he thoroughly enjoyed having my face in his ass. And especially when I jabbed my tongue in his sphincter trying to get my tongue in the opening as far as I could reach.

Sloane directed me to put my hands between Jess’s legs and “fondle and massage his balls and dick”. I couldn’t believe how big Jess’s balls felt in my hand. And when I touched his circumcised penis it felt enormous compared to my own and I could tell it wasn’t even hard, the difference in our cock size made me feel even more inadequate than usual. Between my tongue in his ass and my hand on his balls and dick he quickly was sporting an impressive erection.

My s****r instructed Jess to roll over on his back. He turned over and his thick throbbing nine plus inch dick became the centre of attention. My s****r said, “Needle dick, use your mouth on a real cock and make sure you swallow every bit of cum!”

Although she said it in nice way the effect was still very demeaning but I did as told and massaged Jess’s balls and opened my mouth and tried to put as much of his hard-on in my mouth as I could. I opened my mouth as I went down on his erection and closed my mouth coming back up to the head of his dick. I continued this motion with increasing intensity as I felt Jess respond.

It was then s*******n-old Jess’s turn to be embarrassed because he climaxed really fast shooting a premature load into my mouth. I tried to swallow as much of the goo as I could and licked up the overflow cum as the girls watched.

My s****r said,” You do nice work Little guy, now use your mouth and lick Jess’s dick and balls clean and don’t make a mess in my bed!”

Again I did exactly as told without comment as Jess relaxed with his legs spread and his hands behind his head and a satisfied look on his face. I licked away as Jess lost his hard-on. The girls sat and watched me clean him up and I heard Megan say she’ll like me to give her the same treatment Jess just got, my s****r said, “Sure you can use him anyway you want!”

Sloane instructed me, “After you clean Jess change the bed sheets and take a shower and don’t forget to brush your teeth.”

After I completed those tasks I was ordered to report to the kitchen naked for further instructions. I just quietly responded, “OK” and continued to lick Jess’s balls.

My s****r spoke to Jess and asked him to join her and Megan in the kitchen for a snack after I cleaned him and she told him she’ll love it if he stayed undressed, Jess enjoying himself told her OK. She also said, “Jess, my b*****r will do whatever you want him to and if he doesn’t let me know, there’s no hurry to get downstairs!” and then to me she said, “You hear that needle dick?”

“Yes, Sloane,” I said.

After the girls left, Jess got on his side with his left leg lying straight and his right leg bent up to his chest area. He used two pillows to support the left side of his face so he could easily see to his rear. “Aden, use your tongue on my asshole again!”

He left no doubt from the way the command was given that he felt superior to me. Never the less I not only obeyed him I genuinely tried to please him. I wetly slobbered over his ass and stuck my tongue up his asshole while he moaned with pleasure.

After a time he rolled over onto his back and propped his head up with pillows and bent both knees and held them to his chest by cocking his arms behind his knees. This position gave him a clear view between his legs and he ordered me, “Continue using your tongue in my asshole, pencil dick”.

I crawled between his legs and again used my tongue in his asshole.

Although my face was wedged in his ass we had eye contact. And it was really degrading when he ordered, “Now stick your tongue up my asshole as far as you can and don’t take your eyes off mine!”

So that’s what I had to do while he stared in my eyes with a smirk on his face, I had to jam my tongue up his asshole as he watched me, and we both knew he would never do that to me. He definitely was not being nice but I had to obey him and he knew it.

After a few minutes of wetly snaking my tongue into his ass opening, he said, “OK enough!” and he put his legs down and told me to suck him off.

I did as he wanted and this time it took seven or eight minutes of my mouth going up and down on his huge pole, using a lot of saliva, before his whole body stiffened and he shot off another thick creamy load into my mouth. I swallowed his load and continued to lick him until his big penis was limp and stopped leaking semen.

Jess got up and walked downstairs while I stayed to change the bed sheets and took a shower and naked I walked downstairs into the kitchen. My s****r told me to start tidying up the kitchen but she wanted me to do it with a hard-on. She told me to “jerk off but don’t dare cum”. I bashfully stroked my penis to achieve an erection as Megan, Jess and Sloane talked among themselves. All three of them got a kick out of messing with me.

After cleaning up the kitchen with a hard-on, my s****r told me to lead the way upstairs again. Thinking about “servicing” Megan made it easy to maintain an erection because although I was scared I was very excited.

Upstairs Jess got dressed and Sloane gave me a lecture about none of this being for my pleasure. She said, “Unless you’re able to keep your little dick soft everything is off as far as taking care of Megan!”

She instructed me to stand in the middle of the room and masturbate, supposedly so when I serviced Megan I would be soft. Sloane told me to catch every bit of cum in the palm of my hand and lick it up and she told me I had exactly three minutes or she would get the strap and use it on my ass. I stood with my eyes shut gripping my penis with the tips of the fingers of my right hand and tried to concentrate.

I thought about the three of them sitting there making fun of me which strangely was a turn on and then when the three of them begun calling out demeaning comments like, “My nine year-old b*****r’s dick is bigger than that! That’s the smallest cock I’ve ever seen! Go little guy!” and between these comments they were all yelling chants of, “Beat it, beat it, beat it!”

My knees buckled and so much cum shot out I had to use both hands to catch it.

That’s when my concentration was broken as my s****r instructed me to catch every bit of cum and lick it up. So as my dick shrank and virtually disappeared I was f***ed to lick my palms clean of cum. It was really embarrassing to stand before Megan and Jess trying catch leaking cum from my now really tiny penis. Until it stopped dripping I licked one hand clean as the other one caught more dripping semen fluid.

Finally my penis stopped oozing cum and I stood waiting for instructions feeling too shy to made eye contact with anyone. At last my s****r spoke, “Aden, do you think you could see Megan naked without getting hard?”

I answered with much timidity, “Probably not.”

Sloane said, “Well than, we’re going to end today’s session now and before our next session you’ll use some of your savings to buy a chastity device and some other items.”

Jess and Megan left at that point and I could tell by Megan’s body language and a few things she said to my s****r that she would have preferred to continue but my s****r wouldn’t allow it.

The following week my s****r had me withdraw several hundred dollars from my savings and she accompanied me to a well stocked boutique type sex shop. I don’t know where she got it from but outside the shop she gave me what looked liked a state issued ID card that had my photo on it and my age listed as 18.

Sloane told me to buy two things, a njoy large stainless steel butt plug and a male chastity device. She stipulated that I would have to ask for a male chastity device for a male with a very small penis. I pleaded with her not to make me do it but she insisted.

I was really embarrassed as I walked into the store and when I saw the very pretty young blonde woman behind the counter I couldn’t go through with it and walked out of the store. My s****r was furious, she told me I had no choice, either the salesgirl would know about my laughable little dick or everyone in our school would know my secret.

So given that ultimatum I went back into the store and approached the young woman. Blushing furiously I asked her if she could help me find two items. She said, “Sure what do you need?”

I responded that I wanted to buy a njoy large butt plug. I was stammering so much it was really hard to get my words out. The young woman had me repeat myself and in a too loud voice I repeated myself, still very much uncomfortable knowing what I would have to ask for next.

She had the plug in stock and put it on the counter. She asked, “Anything else?”

In complete mortification I asked, “Do you have a male chastity device for someone with a small penis.”

The young woman said, “Well we have quite a few”. “When you say small penis, how small do you mean?”

I said, “Two and half inches.”

And she asked, “And what size is it when it’s erect?”

I could not have been more embarrassed when I answered, “Two and half inches IS the erect size!”

In a really fake warm voice and a twinkle in her eye she said, “Oh, I’m so sorry”. And then she asked, “And
the circumference? ‘

Afraid to make eye contact with her I responded, “Very thin.”

She said, “Err … that is tiny isn’t it?” and after a pause she continued “Let me think a minute. We do have an extra small clear plastic one with a curved shape that might work if you are careful to adjust it snugly.”

I had her ring both items up and I was out of there.

Once in the car my s****r wanted to see what I had bought and she had me tell her all about what was said in the store. She seemed to relish the humiliation I felt.

The next day after school my s****r required me to use both new toys. I was naked and she had me smear lubricant on my fingers and work first one than two fingers up my butt. This was a first and it was really degrading to perform such an intimate act while she watched closely. It definitely seemed to be a power thing with her. She constantly f***ed me to do things to show me she was the boss.

She sat on the side of the bed while I stood with my back to her with my legs spread wide bent over fully exposed fingering my own asshole for her amusement. She then had me face her and rub lubricant on the butt plug. After which my s****r again made me turnaround. And I had to f***e the big smooth heavy plug up my behind while she watched. It was not easy because I never had anything up my ass before but because of all the lubricant and fingering it finally pop in and it felt huge.

Sloane then had me walk around her bedroom enjoying my obvious discomfort. I asked her why she had me buy such a large butt plug and she answered, “Little guy, that plug is up your ass because it gives me pleasure to know how uncomfortable it makes you feel, not because I want you to enjoy it!”

She then had me put the chastity device on. My penis is so small neither my s****r nor I knew if it would work, she had me stand before her while she sat on the bed and inspected the fit and adjusted the rings so that it fit snug. The key to the fit was how it fit my balls, the fit was important so it would stay in place because my limp penis is too small to aid the fit. A final indignity was the small lock she placed on the device. I don’t know why I didn’t protest the lock but I didn’t.

My s****r looked really pleased with herself as she cupped my testicles she said, “Little b*****r, let’s see if that needle
dick of yours will stay trapped in this device!”

She was wearing a tee shirt and jeans and my mouth dropped as she took her shirt off. She unfastened her bra and it fell away exposing her firm pointed breasts to my eyes, it was the strangest sensation because those were the first real breasts I ever seen and my penis wanted so bad to get hard but the device wouldn’t allow that to happen it.

Next my s****r stood and removed her jeans and then her panties, she sat down and spread her legs, leaned back and said, “Little Guy, tell me what you’re feeling?”

My s****r’s body was fantastic and my penis was trying to get hard but it was prevented from achieving an erection. It wanted so much to be free but it wasn’t able to enlarge so I said, “Sloane this device won’t let me get hard and it’s painful. Please take it off, I promise I’ll obey you!”

Disdainfully Sloane said, “Aden get on your knees and use your tongue on my pussy!”

And that’s what I did, at the same time exploring her pussy with my hands and my eyes. Unfortunately the sensations caused by the plug in my ass and the plastic bind on my dick created almost unbearable discomfort. That discomfort was making it difficult to enjoy the spectacle of my s****r’s juicy pussy crack.

Then my s****r said, “Aden, massage my boobs with your hands.”

I couldn’t believe it but here I was doing things I only dreamed of before. My s****r than instructed me to pinch her nipples and she
told me to keep my tongue busy. I continued that for awhile and then she rolled over and was half off the bed from her thighs down with her legs spread obscenely wide with her ass pushed out. Contemptuously Sloane said, “Little guy, use your tongue!”

Her ass was smooth, firm, hairless, unblemished and inviting. So I tried to ignore Sloane’s haughty attitude as I put my tongue directly on her clean pink opening and worked it in.

My s****r loves it when I use my mouth on her asshole and she had me “worship” her asshole for at least a half hour. She kept
saying, “Little guy, get you tongue up there as far as you can!”

And that’s what I did partly because I was grateful that she let me serve her. But at the same time I was incredibly embarrassed to be required to lick her asshole because, like Jess, I knew she would never perform such an intimate act on me. It just seemed she felt her superiority entitled her to use me for her pleasure.

Finally she was done with me and dismissed me. I ask her to remove the chastity device but she told me it would stay on until she felt like taking it off and she told me not to ask her again but she told me I could take the butt plug out at bed time.

The rest of the week she didn’t have me “service” her but she did require me to keep the chastity device on and clean the house. Friday afternoon as I cleaned her room, nude as usual, she told me that she had agreed to “loan” me to two of her girl friends Saturday afternoon. I was horrified but I knew better than to protest.

Sloane explained that I would go to her friend Jennifer’s house at 3PM Saturday. She explained that Jennifer’s single mother would be at work and Jennifer would have her friend Susan with her. Sloane made it clear to me that I would be required to do whatever they told me to do. Although my s****r did tell me that she had set some rules for her friends to follow which were, no photos, no one else could be present or involved with using me, and they could not physically harm me. Sloane further told me that her friends knew everything about me and they had seen all the photos that my s****r took when she caught me masturbating in her bedroom.

The last few things Sloane told me about the Saturday “loan” was that she had encouraged her friends to humiliate me and she had given the chastity device key to Jennifer to use as she liked. She also admonished me that if I tried to avoid eye contact with her friends by looking at the floor she would punish me. She insisted that I make eye contact.

Saturday for some reason I didn’t even think about not going to Jennifer’s home and I don’t why, I wasn’t pleased with this “loan”. The biggest problem I had with it was that Jennifer was in my home room. I didn’t know her but I had certainly noticed her, she was really nice looking and one of the popular k**s in my class. Despite my nervousness, exactly at 3PM I rang her door bell.

Jennifer answered the door and ushered me into the living room where Susan was sitting. Jennifer said, “Aden, your s****r says
although you have your short comings you really try hard to please!”

Both Jennifer and Susan thought this comment so funny they couldn’t resist laughing. I just stood awkwardly and waited, Jennifer said, “Aden, your s****r tells me that she calls you among other things needle dick is that true?”

“Yes,” I meekly said.

“Well we would like to see your needle dick, take all your clothes off!”

This was said with the assertiveness of someone who knew she would be obeyed.

I took my running shoes off first and then my socks and then my shirt, both girls were watching with interest as I took my jeans off. As I lowered my briefs I looked at the girls but their eyes were mostly glued to my crotch. When my shorts were on the floor I stepped out of them and stood before the girls while they stared at my caged little penis. Jennifer told me to step closer to them so she could get a better look and as I moved closer she put her hand on my ass to guide me in front of them. Feeling her hand on my ass caused my cock to go into contraction but it was prevented from getting hard. Although you could tell by the way it was bouncing around it desperately wanted to be free and hard.

Because the chastity device was made of transparent plastic both girls had a clear view of my penis. Susan said, “Aden, your s****r is right, you have the smallest cock I’ve ever seen!!!!”

As she said that she held my balls in the palm of her hand. My penis was causing the plastic device to twitch and it was obvious that the device was preventing me from having an erection Sloane hardly ever touched me so it was really exciting to feel the girls hands on me.

Jennifer said, “Little guy, turn around.”

I turned my back to them and Jennifer told me, “Spread your legs and bend over and touch the floor.”

I did as told and I felt one of them stroke the inside of my thigh and then I felt one of them part my ass cheeks even wider. My cock was going crazy! Susan said, “We were hoping you had your butt plug in, did you bring it?”

I said, “No I didn’t, my s****r didn’t tell me to bring it.”

While one of them still had my ass cheeks parted Jennifer asked, “Do you do everything Sloane tells you to do?”

Impishly I responded, “Yes, I do!”

Jennifer told me to straighten up and turn around and take a sit across from them. As I sat Susan said, “You’ll have to obey the same rules here as you do with your s****r now spread your legs please.”

So I sat naked in full view of two fully dressed teenage girls with my small caged cock on display.

Jennifer asked me, “Aden, do you like serving your s****r?”

I answered, “I’m not sure sometimes it’s exciting and sometimes it’s embarrassing and humiliating.”

“I see. Well just so you know the same rules that your s****r applies when you are alone with her will apply while you are here with some slight modifications. If you need to use the bathroom while you are here you will ask permission and one or both us may accompany you while you use it but regardless you will not close the door!”

I just said, “OK!” but I thought to myself I wished my s****r hadn’t let these girls know so much detail of the arrangement I had with her.

And I wondered how many other k**s knew I allowed myself to be used and ridiculed by my s****r and her friends.

Jennifer told me, “My mother won’t be home until after midnight and she wants housecleaning and ironing done so for the next few hours you will clean up around here and when you are done with that you will set up the ironing board in the living room and do ironing while Susan and I watch TV!”

I again said, “OK.”

Susan gave me one last instruction before I started cleaning she said, “Aden, during the course of your cleaning if you need to bend over to do something and Jennifer or I are present you will be expected to turn your back to us so your ass and balls are displayed But little guy, to be honest you’re equipment is so small you’ll need to really bend over in an exaggerated way otherwise we won’t be able to see your little balls do you understand what I mean?”

I said, “Yes I understand!”

“Good all cleaning supplies are in the closet off the kitchen, you may begin,” and I was dismissed.

So for the next few hours I cleaned and many times as Jennifer or Susan checked on me they would purposely drop something on the floor and I had to bend over with my backside to them with my legs spread wide completely exposing my asshole and balls to their view and the feeling seemed intensified because they were dressed and I was not.

After I finished the cleaning I had to use the bathroom so I asked Jennifer for permission, and she inquired, “What do you need to use it for little guy?”

I answered, “I need to urinate.”

She said, “Ok I’ll follow you,” and I could feel her eyes on my bare ass as I walked up the stairs.

When we got to the bathroom Jennifer sat on the edge of the tub and because of the chastity device I had to sit on the toilet, and Jennifer thought that was amusing. It was really hard to get a flow going while being watched but with the first sound of my urine hitting the water Jennifer stood in front of me and looked down at me and said, “Aden, as your s****r instructed you, I expect you to make eye contact with me!”

Her movement and voice broke my concentration and I stopped urinating but I looked her in the eyes. Looking down on me and between my legs Jennifer said, “OK little guy you may resume pissing.”

It was really difficult to piss while she watched me. She said, “Hey clit dick, I haven’t got all day!”

As I continued to look up at her my flow resumed and I kept my eyes on hers until I stopped pissing. She keep shifting her eyes from my eyes to my caged dick, not missing anything. When I stopped urinating I shook my trapped penis to stop it from dripping and finally she left telling me “Little Guy, start the ironing now!”

I replied, “Yes Jennifer.”

I went downstairs and Jennifer had a basket of clothing waiting for me in the living room. I set up the ironing board and proceeded to do ironing, the girls didn’t say much to me but they did look at me a lot and once in while they would throw something on the floor in front of the TV during the commercials. I was then told to pick it up and each time I did I had to hold the pose. They both thought it was really funny to f***e me to lewdly expose myself for there pleasure.

After I finished the ironing the girls shut the TV off and Jennifer told me, “Aden, clean up the mess we’ve made we will be back shortly.”

I said OK and about 15 minutes later the girls returned to the living room and both of them had changed from jerseys and jeans to short nighties and they looked fantastic, the nighties showed off there great teen bodies.

Susan said, “Needle Dick, come sit with us” and they both sat on either end of the couch leaving the middle spot for me. When I sat they both moved just a bit closer to me and as if prearranged they both put their hands on the inside of my thighs and spread my legs open a little. Jennifer then cupped my balls in her hand and picked them up a little so my caged penis and my balls were more visible. My penis was really trying to get erect but it was blocked from getting hard.

Jennifer said, “That’s better I like it when we can see your little cock!” she continued, “So tell us how does it make you feel when you’re made fun of because your cock is so small?”

I paused and took a deep breath and was about to deliver a nuanced answer when Susan asked, “Do you like it when your s****r uses you for her own pleasure or amusement?”

I answered, “Sometimes.”

Jennifer took her nightie top off as she put her hand behind my head and guided my mouth to her right breast. While I eagerly put my mouth on Jennifer’s breast, Susan rubbed the inside of my thigh which caused the discomfort level of my trapped dick to intensify.

I could feel Jennifer’s nipple become larger in my mouth as I licked and kiss one breast. She placed my hand on her other breast and told me to rub it. Suddenly she stopped me and had me stand. As I stood before both girls my plastic device was bouncing all around because my dick was trying to harden. Jennifer told me to go to the kitchen and get a glass and return. Confused I just nodded as I walked out to the kitchen with a painful trapped penis as they both watched me leave the room.

Both girls watched me return to the couch and Jennifer positioned me right in front of her where my cock was at her eye level, and she used a key to remove my chastity device. Immediately my sixteen year-old cock got incredibly hard, yes it was tiny and thin but it was as hard as any teenage boy’s cock could possibly be. Its purple head looked like it would burst, Jennifer cupped my balls for a moment but my cock was throbbing and bouncing so much it was clear I wouldn’t last long so she let go of it.

Both girls studied my freed hard-on with interest and finally Jennifer said, “Aden, I have a deal for you. I know your s****r said no photos today but if you let us take one photo of you we will let you cum today. What do you say?”

I was so horny I would have agreed to anything so I said, “Yeah that’s OK!”

They must have had the photo planned because they positioned me in the middle of the room standing at an angle to Susan who was kneeing a few feet away aiming a digital camera at me. Jennifer knelt and took a position to my right facing left at eye level to my very erect penis. Jennifer held a finger under my dick and told me to smile. As I smiled Jennifer substituted her finger for a clear six inch plastic ruler with large numbers and measurement lines and Susan snapped the photo.

They both laughed hysterically and Jennifer slapped my ass hard and told me I was a good sport. I was quickly diverted from hurt feelings because of the ruler mockery back to arousal as Jennifer’s hand lingered on my ass after her slap.

Susan handed me the glass while Jennifer went from massaging my ass to slipping a finger up and down my ass crack. Then Susan told me to masturbate and catch my cum in the glass. My natural shyness to do that was conquered when Jennifer spit on her third finger and slipped it in my asshole.

While she gently massaged and finger fucked my asshole, I quickly stroked myself to orgasm. It was an amazing feeling to stand there with a pretty girl’s finger in my rectum while they both watched me masturbate. At that moment I didn’t care that they both thought of me as a wimp with a little dick.

My cock continued to leak cum while I pulled the skin up and down squeezing the cum into the glass. There must have been two ounces of semen in the glass when Jennifer said, “Aden, you’ve got the smallest erection I’ve ever seen!”

Here take a look at this and she held the back of the camera to my view and showed me the picture they had taken. Unfortunately for me it was an excellent photo framed just right. It showed me naked from my knees to my head with Jennifer kneeing holding a ruler under my penis which clearly showed that my penis was erect and only two and quarter inches in length.

When compared with Jennifer’s finger in the photo it was obvious that my cock was not the least bit thick. And to top it off, I had a foolish grin on my face. I think part of me felt I deserved some level of humiliation because of my inadequate little cock but if the girls circulated this photo it would be really cruel of them.

“I think you deserve a toast little guy!” Jennifer continued, “Pick up your glass and make sure you drink all of your toast!” and keeping my eyes on their eyes that’s what I did.

I drank down my cum in two gulps.

Jennifer stood up and removed her nightie bottom and my eyes went immediately to her pussy which was thinly covered with brunette hair that had a sheen that was really appealing. There wasn’t an imperfection on her teen body although I had just cum, I could feel my penis start to harden again.

She lay down on the plush carpeted living room floor on her back with her legs bent at the knee and her legs spread opened and said, “Aden your s****r says she’s taught you to use your tongue, crawl between my legs and show me what you’ve learned!”

Susan spread out on her side across the couch with her hand in her bottoms rubbing her crotch as she watched me get between Jennifer’s legs.

I was able to caress the inside of Jennifer’s thighs and use my fingers to open her pussy lips to my sight and used my tongue just the way my s****r taught me to. After spending twenty minutes trying to please her and after a series of thundering moans she just grabbed my head with her thighs and her hands and stopped me. As her breath became more normal she run her hands through my hair and said, “Little guy, that wasn’t bad!”

Jennifer asked Susan, “Hey Sue, you ever have your asshole licked?”

Susan responded, “You mean he does that too?”

“Yeah, Sloane requires him to, isn’t that right little guy?”

I shyly answered, “Yes”.

And Susan said, “I’ve never had the nerve to ask a boy for that”, a moment later though she said, “I’m game”, as she hopped
off the couch she used her hand on my shoulder to guide me onto my back and in the same motion removed her bottoms and squatted over my face, looking towards my penis.

I looked up and could see her naked hairy pussy and asshole as she lowered herself into my face leaning forward so she wouldn’t suffocate me with her ass. “Needle Dick, lick my asshole,” Susan said this as if she thought of me as a slave.

And once again I put my mouth on an asshole. Licking, sucking, slurping and especially pushing my tongue up her opening. And just like Sloane and Jess before her, Susan loved it. She said things like, “Oh baby, yes yes yes!” and then, “Needle dick you are good! I love the things you do with your tongue!”

While my face was buried in Susan’s behind, Jennifer laid her head on my lower abdomen and begun massaging my balls and touching my penis with her fingers. Although I had just cum my little cock got hard again.

I suddenly got the surprise of my young life as Jennifer put her mouth on my penis. She easily deep throated my little cock. And as she increased the pace of her up and down motions on my cock I increased my tongue jabbing of Susan’s asshole. Just when I thought the sensations couldn’t get better I felt Jennifer poking around my asshole and slide a finger up my bum hole and it felt incredible.

I could feel myself about to cum and took my mouth off Susan’s asshole long enough to say, “I’m going cum, I’m going to cum!” but Jennifer kept her mouth on me as I arched my back and shot out a load right into her waiting mouth, simultaneously I buried my tongue as deep as could possible get it into Susan’s asshole.

As I did that Jennifer swallowed my cum and kept my dick in her mouth until I had lost my erection licking it clean as it disappeared into my foreskin.

Jennifer has not put her mouth on my penis or put her finger in my ass or tried to please me in any sexual way since that day. She does use me to orally satisfy her and massage her sometimes but she no longer reciprocates in any way. She also uses me for errands and cleaning.

Both Susan and Jennifer have let some k**s see my ruler photo which is embarrassing but there is nothing I can do about it. And my s****r has shown my naked photos to lots of other k**s. I originally allowed Sloane to blackmail me because I was afraid she would tell the k**s in school about my undersized dick. Now most of the town knows me as the k** with the little dick who will do anything Jennifer or his s****r tells him to do, strange how things turn out.
100% (8/0)
 
Categories: BDSMFirst Time
Posted by klammer
7 months ago    Views: 1,169
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