Assignment #14: A Chance to Cum

Mistress ordered me to go to her blog and read through all of her captions and comment on each one. There were many and it was exciting to go through and see all of the scenarios she had created and also a little humiliating to see what the sissies were being forced to do. For 10 captions I had to stroke my pink vibrator, then for another 10 I had to suck on it, then the final 10 I had to slip my butt plug into place as well. Afterwards I had to pick my favorite caption and cum on my dildo while looking at it and then lick all the cum off.

This was my favorite:














I imagined myself as "Sierra" in this picture, being slowly feminized by a sweet controlling girlfriend. I would be so eager to please her, and so happy to see her satisfied that I would obey her every command. I would eagerly wear stockings, eagerly wear lipstick, and quickly agree to everything she asked. I would love to have her make my sissy feelings a reality and would let her take complete control. While being forced can be erotic this system of "rewarding" the sissy for her good behavior seems even better to me. I can tell that the sissy just wants to see the woman pleased...just like I would.

As I mastrubated to this picture I imagined myself pleasing my Mistress, her saying "good girl, you'll do anything I ask won't you?" I came and smeared it all over my pink vibrator and then stuck it in my mouth. I've eaten my cum before so the taste wasn't a total surprise, but it felt so humiliating to have to lick it up off the vibrator to feel it sliding on my lips as I worked to get it all into my mouth. I licked it up eagerly, sucking and slurping it down, knowing that as a sissy it was my job to please my Mistress and that this is what she wanted. I also felt so relieved to have the chance to cum and know that only through obedience will I be allowed release. So I savored the moment and enjoyed my cum covered vibrator and hope that my comments and description have pleased my Mistress.

Assignment #13: Girlie Magazine, Nails, and a Dildo

For the next task after my humiliation at the lingerie store I was expected to do my nails, read a girlie magazine, and then suck my dildo for 15 minutes while looking at a picture from it.

I picked up a Cosmopolitan on my way back from VS, the August 2010 issue with Britney Spears on the cover. I couldn't decide on a nail polish for my toes, but eventually settled on pink (which matched both the cover of the magazine and my pink vibrator).

Like a good sissy I sat down to do my nails, carefully trimming them and buffing them, then applying the polish and topcoat. The whole while I read the Cosmopolitan. It was full of plenty of feminine advice from makeup and clothes to dating and sex. Something tells me the article on artificial insemination/sperm banks won't be particularly useful to a sissy like myself, but there was plenty in there that I am sure is good to know. And like any magazine designed for women there were plenty of pictures that excite a sissy in their femininity. There was no doubt that I was a sissy at this point. No man would ever pretend to be a man with a dildo in his mouth, a cosmo for inspiration, and painted pink nails. This is my fate as a sissy.

The picture I chose to suck to was on 222, in the fashion section. While there were many good options of pictures to "inspire" this sissy I found this one especially exciting since the very cute looking woman seemed to have a look on her face that made me blush while I thought about filling my mouth with a vibrator. The look seemed to say "you are such a pathetic and amusing sissy, I am so much better than you." I could not resist it. Like a good girl I got to work and wrapped my lips around my pink plastic friend. Sliding my lips up and down and seeing the look on the woman's face, and thinking about the day's earlier adventure to Victoria's Secret I found myself blushing and hard at the same time.

Assignment #12: Lingerie Shopping Humiliation

For my next assignment Mistress ordered me to go to a lingerie store while dressed in my favorite panties to inquire about sexy lingerie that would be a "gift" for my girlfriend.

Like a dutiful sissy I slipped into a pair of VS panties that I have that are a cute white and pink lace pair and hopped into my car. The town I live in is relatively small in size and there aren't a lot of stores where lingerie (especially sexy lingerie with plenty of salesladies) is available. I considered initially going to a department store, but decided on going to the ever popular Victoria's Secret.

The store I chose was not terribly busy when I arrived, there were a few women looking at panties, but in general it was pretty empty. A little bit nervous I walked in and began looking around, doing my best to attract the attention of a saleslady. Of course, one soon arrived.

The woman who found me was named Carrie and she was a cute petite blonde who was more than happy to help me in the predicament Mistress created. I explained to her that I was looking for something for my "girlfriend" and that we were about the same size. The look she gave me didn't necessarily indicate that she had totally seen through me, but it was clear that she had either quickly decided that my skinny body was not something most girls would be eager to date and therefore wondered what kind of woman might, or that I was indeed the one buying lingerie for myself.

Carrie gladly showed me to the section of sexy lingerie they had and quickly made a couple recommendations on what she thought would look good. I have linked a picture of one of them below. She was quite tactful suggesting all sorts of things and sized me up at about a medium. Then I made the mistake. While looking at the polka dot babydoll apron I described it as "cute." Though there may be men who shop at VS most probably don't say anything is cute, maybe sexy, maybe hot, but not cute. She giggled, I blushed and felt totally humiliated. We looked at a few more things and then eventually I said I'd just have to think about it.

She smiled at me, I'm pretty sure knowing full well who the lingerie was for at this point and said "I bet you do."
















I hope that pleases Mistress.

Assignment #11: Gagged Story

As requested Mistress is having me write a story about a guy tricked into becoming a sissy while wearing panties as a gag and my pink butt plug...here goes...


My hands are tied behind me in the chair and I am blindfolded and gagged with my own cum stained panties. I can feel the butt plug filling me and the soft breeze of the fan blowing over my stockinged legs. My cock, locked in chastity, strains at its unfamiliar surroundings and I let out a small whimper.

I guess this is what I deserved.

It all started with a simple online romance. Nothing big, no weirdness. I just wanted a companion, maybe try out a couple dates and see where it led from there. She was beautiful, smart, attractive, had a nice job, and was quite friendly with me. Maybe she was almost too easy of a catch. I thought I had things made. We went out to dinner a few times, had a couple fun evenings, but nothing especially out of the ordinary. She was hesitant about getting more physical with me but I just figured she had gotten out of a bad relationship and wanted some space and time. Little did I know.

Things started to change a little when she asked me to shape my eyebrows. It seemed like an out of the blue request, but who was I to deny her. She said she just wanted them cleaned up a little, that it was a pet peeve, she didn't like hair, and liked a neat looking guy. So I went along with it, even when her friend at the salon seemed to get a little carried away with the arch. She laughed and said it framed my eyes well. I got a long kiss for that one, and forgot my worries right away.

My facial hair was next to go, I did that without her asking. I figured she didn't like bushy brows, so why should she like a beard? I was right, she responded favorably. An amorous session of feeling on her couch seemed to be my reward for good behavior. While kissing me she suggested that I should simply take care of the rest of my "beastly" traits as she called them.

So like a fool, I complied. Down the drain went my leg hair. Smooth and (so I thought) sexy for her, I returned and once again was greeted with praise and some amorous advances. We had a wonderful meal and a bottle of wine and then I began to feel a little dizzy. When I woke up I was here. Plug in my butt, dressed in women's clothing, made up like a slut, and tied to a chair. She sat in front of me on her couch, relaxed and sipping a wine glass. I made a sound in my panty gag, but she just smiled and ignored my plea to remove it.

"Well, well. I am sure you are a little confused. No matter. Yes, I did drug you to get you into this position, but it was for your own good. I didn't want to have to work any harder than I had to and I figured I would at least let you have the dignity of a choice. I know your fantasies. I checked through your online history when we were over at your house the other day. You want to be a sissy, and I can help you. I've already quickly molded you into the perfect girl, smooth and service oriented. You are so eager to please me, so willing to obey my commands. I want you to be my new sissy maid and you will start tonight. I have the key to your chastity belt and have invited a party of my friends over for cocktails. You will be serving us all...if you choose. Of course that choice is up to you. I took the liberty of dressing you in your own sissy things, I hope I picked a good outfit, I think you look great in it and I am sure you will do a fine job...but that is up to you. I will leave for an hour. The key to the chastity belt is on the table. Your ties are loose, simply slip out and leave. You'll have to trot home in your sissy things, but you are free to go...

However, you may also simply stay in waiting. If you do, you will be my sissy slave. You will do as I ask, you will never be a man again...not that you ever were...and you will please me in every way I demand. It is all up to you."

With that she stood up and set the key on the table.

I sat there, thinking for a moment.

Could I turn down this woman?

Could I deny my feelings?

She tricked me so completely into thinking I was simply a nice guy she would want to date.

And now to be her slave?

The clock ticked.

I didn't move.

The footsteps came up the staircase. I blushed in fear and eagerness. I was to be her sissy.

Assignment #10: More Captions

As requested by my Mistress, here are more captions.

Assignment #9: Punishment

While Mistress was generous enough to allow me to enjoy the weekend, I did, as expected receive a punishment assignment to go with my time off. A sissy must always take punishment with an appropriate dose of gratitude, and I am very grateful my Mistress was nice enough to punish me as she did without too much pain or humiliation.

As required by Mistress I pulled out a pair of my panties and stuffed them into my mouth, completing the gag by tying a pair of pantyhose to hold them in. I bound my hands holding my pink vibrator and sat down in my closet as required and began to stroke the vibrator. Mistress required that I do this for 15 minutes so I set a timer and then simply focused on the hard toy in my hands. While one might not think that a hard plastic vibrator is a good representation of a cock a horny sissy with a prompt from her Mistress, a set of orders, and a vivid imagination needs little help to begin imagining that the hard thing in her hands is a man's cock that she has been ordered to pleasure. While my hands were bound I tried different techniques on the cock, stroking slowly at first and then increasing the pace, using different amounts of pressure, focusing on one side or the other. I imagined the man moaning with pleasure as I stroked him, his cock nice and hard, the precum beading at the head. Of course as I did this for my Mistress I became hard and eager, but like a good girl I did not cum. While I have never jacked a man off before I found myself about 10 minutes in wishing that the imaginary cock I was working would cum to give me the satisfaction of pleasing the man and my Mistress. I imagine him moaning in pleasure and my hands being covered in his warm sticky cum. Unfortunately all I got to tell me that I was finished was the buzz of my timer, but I am sure Mistress will be pleased to know that this sissy felt like a naughty slut, bound and forced to jack a man only to find she wanted to see him pleased.

Assignment #8: Sissy Thoughts

I was gone for the 4th of July weekend and my gracious Mistress was kind enough to simply allow me the time off with only minimal punishment. However, as to be expected I also had to be a good ladylike sissy and refrain from cumming. Having been denied the chance to cum already for a while I was quite eager and my thoughts often turned to sissy things over the course of the weekend.

Naturally 4th of July means a lot of time spent outside which means much time to observe the fairer gender showing off their best summer wear. As any sissy would I couldn't help but become jealous at some of the articles of clothing that I saw. I did not so much want the women in them as I wanted to be those women, beautifully dressed, and pretty.

One of the things that I noted with a special amount of jealousy were cute wedge sandals. In the past I've occasionally seen wedge sandals or espadrilles (as I found some are called) and found them to be out of place in an outfit but for the early July summer outfits they looked perfect. They look casual without feeling lazy, and show off beautiful smooth legs, and perfectly pedicured toes while accenting summer outfits with an appropriately feminine and summery shoe style. While flats or flip flops might be more comfortable and standard heels more appropriate for an evening outfit I couldn't keep my eyes off of the wedge sandals...and naturally the painted nails in them. Summer is the perfect time to show off feet, and nearly all of the women I saw over the long weekend had their toes painted in various shades of reds, pinks, purples, and even some more irregular colors. Walking by a nail salon I looked on in envy as two women sat there patiently getting their toes and fingers done. Summer of course brings out many other things a sissy desires, flowing dresses, short floral patterned skirts, halter tops, and cute women's sunglasses. I spent much of the weekend watching and envying each woman and her pretty outfits.

Of course not all of my sissy thoughts were merely on outfits, Mistress kept me nice and horny all weekend and my thoughts naturally turned to what she had in store for me. I of course wondered how much more of a chatroom slut she would make me, but I also imagined some of my captions and the situations within them, women with strapons, me as a beautiful sissy restrained and awaiting my Mistress' orders. Each time these thoughts entered I did my best to not let myself get carried away and masturbate. Luckily I was able to make it through the weekend. I do wonder though what Mistress has in store for this humble sissy.

Assignment #7: Sissy Servicing

Mistress Jessica asked that for my next assignment while in full drag I must go into club sissy, find a sissy and service her fully while stroking my pink dildo. As usual I am allowed to touch myself, but not allowed to cum at all. Here is the transcript of my servicing...It took two tries to actually service a sissy to completion, the first left...mid suck...

I simply started by saying "Any sissies need their cock serviced?" the first one came quickly to me, the second one was much harder to find...

[jamielle] 7:25 pm: you may service me
[bethbloom] 7:25 pm: What are you wearing?
[jamielle] 7:26 pm: i've got a thong, miniskirt, and bra on
[bethbloom] 7:27 pm: let me slide it off for
you
[jamielle] 7:27 pm: -i bite my lip and moan
softly-
[bethbloom] 7:27 pm: I lick my lips eagerly
[jamielle] 7:27 pm: -lifting my butt up
enough for you to slide the thong off-
[bethbloom] 7:27 pm: I slide your thong off
[bethbloom] 7:28 pm: I slide my fingers up
along your thighs again
[bethbloom] 7:28 pm: tracing my nails
along the inside of your leg
[jamielle] 7:28 pm: -i close my eyes and
moan softly at your touch-
[bethbloom] 7:29 pm: I kiss the inside of
each thigh
[bethbloom] 7:29 pm: my hands creep a
little farther towards your skirt
[jamielle] 7:29 pm: -i bite my lip again-
[bethbloom] 7:30 pm: my right hand slides
up your mini skirt and I feel for you
[jamielle] 7:30 pm: mmmm, that's it
sweetie, keep going
[bethbloom] 7:31 pm: I slide your skirt up
with my left hand to get a better look
[bethbloom] 7:32 pm: I gently run my
fingers along your length
[jamielle] 7:32 pm: mmmmm, that's it
sweetie. play with my 7.5 inch cock
[bethbloom] 7:33 pm: mmm, so big
[jamielle] 7:33 pm: just the way sissies
like it
[bethbloom] 7:33 pm: my left hand gently
encircles your balls
[bethbloom] 7:34 pm: my right grasps you
softly and begins to stroke you
[bethbloom] 7:34 pm: I move up and down
slowly
[bethbloom] 7:34 pm: and let out a soft
moan
[jamielle] 7:35 pm: -i bite my lip and moan
softly- mmm beth, that feels good
[bethbloom] 7:35 pm: I brush a little
precum from the tip of your cock and
massage you with both handsd now
[bethbloom] 7:36 pm: letting them gently
encircle the head as they move up and
down
[jamielle] 7:36 pm: -moans a little louder-
[bethbloom] 7:37 pm: I speed up a little
[jamielle] 7:37 pm: mmmm, kiss it beth
[bethbloom] 7:37 pm: tightening and
loosening my grip as I move up and down
your hard cock
[jamielle] 7:38 pm: mmm, that's so good
beth
[bethbloom] 7:39 pm: my hands move
down to the bottom of your cock and I
open my lips and move towards you
[bethbloom] 7:39 pm: I let my tongue
gently graze the head of your cock
[jamielle] 7:39 pm: -i moan your name
softly- suck that cock beth
[bethbloom] 7:40 pm: I smile at you, as
you please
[bethbloom] 7:40 pm: my lips part and I
take the warm head in my mouth flicking
my tongue over it
[jamielle] 7:41 pm: i'm sorry beth,
something just came up i gotta go
[bethbloom] 7:41 pm:
[bethbloom] 7:41 pm: that's a shame
[jamielle] 7:41 pm: -pulls you into a kiss-
[bethbloom] 7:41 pm: sometime soon
[jamielle] 7:42 pm: you're a very good
cocksucker, if they're available i'd like to
make y=use of your servicwes again
[bethbloom] 7:42 pm: *Kiss*


And them attempt #2:

[nancyboy60] 8:28 pm: and how would
you do that younglady?
[bethbloom] 8:28 pm: my Mistress has
asked me to service sissy cock on here,
and I would be very pleased to service
yours
[nancyboy60] 8:29 pm: is your mistress
there with you?
[bethbloom] 8:29 pm: oh no, not at the
moment, but I must copy the text of my
chat for her
[nancyboy60] 8:30 pm: is your mistress in
here or at home?
[bethbloom] 8:30 pm: she is online, from
Club Sissy
[nancyboy60] 8:31 pm: well all im wearing
is panties and bra
[bethbloom] 8:31 pm: that is fine, I will
please you as you are
[nancyboy60] 8:32 pm: as long as you are
an adult
[bethbloom] 8:32 pm: oh yes, 26
[bethbloom] 8:33 pm: sit back and relax, I
will take care of your needs
[nancyboy60] 8:33 pm: ok but please refer
to my cock as a clit
[bethbloom] 8:33 pm: yes nancy, as you
wish
[bethbloom] 8:33 pm: I would love to
service your clit
[nancyboy60] 8:34 pm: i am a sissy and a
sub
[bethbloom] 8:34 pm: relax nancy, I will
please you regardless
[nancyboy60] 8:34 pm: ok
[bethbloom] 8:35 pm: let my hands slide
your panties off
[nancyboy60] 8:35 pm: ok
[bethbloom] 8:35 pm: I kneel down in front
of you
[bethbloom] 8:36 pm: my fingers caress
the inside of your thighs
[nancyboy60] 8:36 pm: oh my
[bethbloom] 8:36 pm: I stroke my hands
up your legs and around your stomach
[nancyboy60] 8:37 pm: mmmm
[bethbloom] 8:37 pm: I circle your clitty
with my fingertips
[bethbloom] 8:37 pm: sighing slightly
[nancyboy60] 8:38 pm: ohhhhh i look at
you
[bethbloom] 8:38 pm: I rest my left hand
under your balls cupping them softly
[nancyboy60] 8:38 pm: yesss
[nancyboy60] 8:38 pm: i oprn my legs
[bethbloom] 8:39 pm: my right hand
closes around your clitty
[bethbloom] 8:39 pm: stroking it gently
[nancyboy60] 8:39 pm: my clit is getting
hard
[bethbloom] 8:39 pm: I look at it eagerly
[bethbloom] 8:40 pm: my fingers tickle its
head a little
[nancyboy60] 8:40 pm: i moan slightly
[bethbloom] 8:40 pm: I wrap my right hand
around it and tug gently
[nancyboy60] 8:41 pm: ughhhh i relax and
close my eyes
[bethbloom] 8:41 pm: I begin to stroke you
[bethbloom] 8:41 pm: letting both hands
work slowly up and down
[nancyboy60] 8:41 pm: ohhhhhh im
getting hard
[bethbloom] 8:42 pm: I lean down and lick
the head
[nancyboy60] 8:42 pm: ohhhhh yes
[nancyboy60] 8:42 pm: im just in my bbra
[bethbloom] 8:42 pm: I open my lips and
moan
[bethbloom] 8:42 pm: taking the tip into
my mouth
[bethbloom] 8:43 pm: my hands gently
caress your thighs
[bethbloom] 8:43 pm: and I take your clitty
in my mouth
[nancyboy60] 8:43 pm: omg
[bethbloom] 8:43 pm: I slurp eagerly
[bethbloom] 8:44 pm: my fingers stroke
the inside of your thighs
[nancyboy60] 8:44 pm: mmmnmmmm
[bethbloom] 8:44 pm: I moan and slide
my lips all the way to the bottom of your
clitty
[nancyboy60] 8:44 pm: oh yes
[bethbloom] 8:45 pm: I begin to bob up
and down slowly
[nancyboy60] 8:45 pm: getting close
[nancyboy60] 8:46 pm: feels so good
[bethbloom] 8:46 pm: I speed up letting
my tongue swirl around your clitty
[nancyboy60] 8:46 pm: yes
[nancyboy60] 8:47 pm: omg so good
[bethbloom] 8:47 pm: sucking, slurping,
I moan and push harder
[nancyboy60] 8:47 pm: cumming
[bethbloom] 8:47 pm: I eagerly begin to
swallow it slurping down every drop
[nancyboy60] 8:48 pm: lick it up
[bethbloom] 8:48 pm: I suck your clitty
getting the last cum out of it
[nancyboy60] 8:48 pm: thanks
[bethbloom] 8:48 pm: thank you
[nancyboy60] 8:49 pm: gotta run
[bethbloom] 8:49 pm: okay bye

Assignment #6: More Captions

After working myself up with the last assignment it took all my sissy strength not to cum with my butt plug in as I looked for more arousing sissy pictures and created captions for them. I hope these captions please my Mistress greatly.

Assignment #5: Exciting

Reading it, today's assignment from Mistress Jessica sounds simple: find an exciting picture, and then suck on my vibrator for 15 minutes while looking at it. However, as Mistress has ordered me not to cum yet, being able to look at a very exciting picture, while filling my mouth, and desperately wanting to play with myself to release left me feeling very horny indeed. My pink vibrator is hard plastic but even feeling that moving in and out of my mouth made me feel like a slut. I could see the smear of my lipstick on it and licked and sucked it eagerly. While I've played with my fingers a little before and have put the vibrator in my mouth before I have never sucked for this long. I felt so humiliated sitting there in full drag, such a feminine feeling, pushing my lips over the pink vibrator so eagerly for my Mistress. I couldn't resist of course, and it only made me want to do more, to continue to please her, but at the same time I couldn't help blushing. No man would ever do this, and as Mistress knows so well, I am no man. The whole time I sucked I looked at the picture imagining myself to be the woman on her knees, so eager, so ready, and I imagined the standing woman to be wearing a strapon, her hand resting on my head, forcing me to suck, slurp and please her dildo until my mouth was worn from the effort. After 15 minutes my mouth and jaw felt a little sore...maybe that will fade with practice, but I was still desperately horny...which was not helped by my next assignment: to caption 5 more pictures while filling myself with my butt plug. I lubed up my sissy pussy, obediently slipped it in, and dripping from my eager clitty got to work on my next assignment hoping desperately that Mistress might allow me the chance to cum soon!