Sissy's Decline into a Slut Pt. 01

The morning comes and I am feeling sissy girly as I dress up and watch my video from last night. I lounge around a bit and have a coffee. I look at sex and BDSM stuff online and get ideas. Bondage gear including locking wrist cuffs and a cool self bondage tool. An ice lock. You have this two piece kit where you fill with water and let freeze. Once frozen and with bondage gear one can lock themself up and until the ice melts enough you are locked in whatever way you set up.

Fucking cool way to play self bondage. I also look at dildos. Of course like all sissy sluts we all dream and desire the 12 inch long, thick black ones. But I know being virginal up my sissy ass that would be too big, so I look at other choices. Anyways I get some cool ideas and figure maybe I should buy stuff?

Well it's back in 'regular male world' and off to my regular male life job I go. But all day on my mind is BDSM stuff and dildos. Driving home after work I swing by a local adult sex shop. Nervous I step out of my parked car and then inside this shop.

I wander around, nervously mesmerized at the sex and BDSM stuff. It's quite infatuating. Out from the back walks a young lady, attractive but not stunning, tall for a girl, oh maybe 5'7" but in heels she's over 5'10", a black dress and black hose or maybe stockings on her nice legs. Hard to tell as her dress is covering from her knees up. Her hair is long full, straight and blonde. Her makeup is a bit on the dramatic side with smokey eyes and blood red lips. She says, "Hello! how are you today?"

I choke a swallow and reply, "Hi, Good... I'm good."

"So what brings you by today?"

I am so fucking nervous but I keep composed, "Um I was just curious, ya know just looking at things."

She smiles and says, "Well hun, that's ok, enjoy looking, I'll be right over at the counter if you have any question or needs."

I smile and say, "Oh, ok ma'am."

She turns and walks away wearing a gorgeous pair of oh maybe 4 inch spike heel black patent pumps. The lovely click clock sound of her heels on the floor helps make my cock go hard in my panty as I am wearing a black panty without padding and pair of black sheer pantyhose all under my guy clothes. I'm thinking 'Fuck I wish I was wearing a pair of my high heels here with her.'

I walk around a bit, I see some leather stuff for males and females, some sexy lingerie, make up, some super tall heels, and BDSM stuff. As I walk to the counter near by her I see sex, crossdressing, sissy and BDSM magazines. I stare at the covers of the crossdressing and sissy magazines. The lady sees me and I'm not sure if she picked up on my staring at crossdressing and sissy magazine covers.

She says, "See anything you like hun? Do you have any questions?"

I'm thinking, 'Fuck I did not come here just to look, I want to buy some stuff if the store has it." I ask, "Um... yeah...ahh..D...Dildos...you g..got any I can see?"

She smiles and her girl next door attractiveness and her sexy outfit compels me to listen to her reply, "Dildos, yes, sugar we have very many to choose from, come over here." as she walks to an area behind the counter she asks, "Are you looking for a dildo for your girl friend or wife?"

I want to say yes but ask, "Um does it matter much?"

She says, "Well hun, dildos come in different sizes and girths, some girls like vibrating ones, some girls can handle big, very big ones. Using one vaginally may be different than anally?"

I ask, "Oh.. um.. I... I have to be honest.. it is one for me."

She smiles and says, "No problem dear, we will have a dildo that you will like." Sensing my nervousness she adds, "Darlin, don't worry, many men buy dildos for themselves. it can be quite fun."

I say, "It's just all sort of weird for me, I mean my daily life is rather normal and mundane. Shopping for a dildo to use on my self is so odd."

She smiles, "Darlin, don't worry, sexuality is a most personal thing, learning to understand your own sexuality and accept it will only make it more pleasurable for you. Humans don't just fuck or have animal sex like other animals, we fuck and do other sexual things for pleasure. It could be boy, girl, boy, boy, girl, girl or just by your self exploring your ideals and feelings."

I reply, "Wow ma'am you really do make this seem...well, you know, more normal...more ok."

She adds, "It is, it is more normal than you think. Lots of otherwise typical guys love the feeling of a dildo, maybe in their mouth but for most up their backside. It would blow your mind the cross section of guys, age, race, status, gay, bi or straight who get a kick out of dildos. Not just us gals use em to play with." as she giggles.

"Oh ok then," I say.

She introduces herself, "By the way, my name is Jill, sweetie."

I reply. "Hi... my name is Phil. But if I can be more upfront, I'm a crossdresser too and my feminine name is Chantel, I'd enjoy you calling me that please."

"Chantel is a cute name," she pauses and looks at me."You look like a Chantel," she adds more, "So any idea of the type of dildo you may like Chantel?"

I reply, "Um, ah not sure."

Jill says, "Well let me help, now I know that many guys often think getting one like this." As she reaches for one. "big black, thick job. It's twelve freaking inches long and two or so inches thick." she giggles as I look at this monster. "But honey, unless you have a well used backside it may not be one you will be able to use and enjoy. What type of anal play have you done Chantel?"

I'm so bewildered about what we are talking about, "Um Jill, I... I .. guess I'm a virgin with anal play."

Jill says, "That's good info hun. Here lets look at this dildo." she puts the big black monster back on a shelf and grabs a pinkish/fleshy number. "This one Chantel will be an easier one for you to break your backside into the world of anal play. It's about seven inches long and only a bit over one inch in diameter. It's nicely shaped head is slightly tapered to help an anal virgin get it working well. This would be my choice for you dear."

I am blushing but ask, "Um, ok... how much is it?"

Jill says, "$24.95. But you will need a good lube for anal work, let me suggest a good lube especially for a newbie?"

I say, "Ok Jill."

She brings out a tube of lube that is designed to not only give long lasting and very slick effect but ingredients that help relax the sphincter. This tube is also $24.95. She says if I want to have some simulated cock sucking fun with the dildo get some flavoured lube too and she shows me a few bottles of flavoured lube. I choose the four pack, Cherry, Mint, Chocolate, Fruit Punch. It is $29.95.

I ask about wrist restraints next and mention this thing I saw, an ice lock for self bondage? Jill pulls out a few wrist cuff choices and I choose a cute pink and black leather adjustable wrist cuffs. As to the ice lock, Jill brings out the item, it's cylinder type thing with a piece fitting inside. If you fill it to varying levels with water, freeze it and attach it to the wrist cuffs I'm buying it will keep my hands/wrists bound until the ice melts and I can pull it back apart. Jill tells me depending on how much water I use how long I let it freeze and the temperature it is at where I use it the time of locked up effect can take up to two hours. Less water, warmer ambient temperatures and such and the time for the ice to melt will be quicker. It's all trial and error.

This stuff is making me so fucking hard in my pants. I choose to buy all these items with excitement. Jill senses my thrill.

She says, "Chantel, you look as if you will get some good play out of this stuff, I hope you do. I've been selling in this field and helping, men, women, guy/gal couples, gal/gal couples and guy/guy couples explore their sexuality for a long while. It makes me feel good to know I help people enjoy sexuality and play. You are quite typical even if you feel odd here today hun."

I'm feeling good now and smile as I say, "You have been so open, kind and professional Jill. You do not judge me and even knowing I crossdress and want to play with all this while I crossdress. I look forward to maybe buying other toys and such here later."

I had a desiring thought and had to ask Jill. " Um... ahhh... noo I bet... better not."

Jill asks, "Hun, ask me what you want, it's ok I see and hear a lot of hot, cool, sexy erotic stuff."

I interject, "Oh ok, I don't know why but I so want to drop to my knees and submit to kissing your lovely black patent spike heel shoes and run my hands on your stocking clad legs. It's silly, I'm sorry for even saying this."

Jill laughs, "Why not? I see you have had a hard on in your pants since being here. I obviously excite you. How about you drop your pants so I can see you panty and pantyhose?"

I cough and say, "Re... Really? Oh my God, umm... ok, oh my God I'm horny."

Jill takes me more discretely behind the counter and sits on the high stool, extending her legs and heels out before me and has me stand before her. She actually undoes my belt and pant's fly allowing my pants to drop. My black satiny panty and black silky sheer pantyhose is out in the open to be seen. My hard on is like a tent rod.

Jill says, "My, my the sissy is all excited. You may drop to your knees now."

I state, "Yes ma'am." as I fall to my knees. I look up at her and she says, "Go ahead hun, kiss my shoes."

I begin excitedly kissing her heels and it was so erotic, my sissy dick wanted to explode with cum. My hands now delicately run up and down her stocking clad calves. Jill enjoys seeing this but my one hand soon plays with my dick while it still is encased in my panty and pantyhose. I continue to kiss her shoes and my left hand continues to run up and down her calves. But I can't contain myself and I cum in my panty, soaking it with my sissy jizz. I'm am in ecstasy. Soon I do my pants back up and feel deep shame.

Jill asks, "Did you enjoy that Chantel?"

I say, "Um yeah it was great but I feel like shit now, so fucked up as a guy."

Jill clearly states, "Hun never feel bad about your own sexuality. Have fun, you like crossdressing enjoy it. I enjoyed seeing you have fun kissing my heels and rubbing my stocking clad claves with your hand while you jerked yourself off with your other hand."

Soon I am standing back up, cum has soaked a bit of the front of my pants now, but it's ok, Jill laughs and says, "Enjoy the wetness from your cum in your crotch hun."

I'm embarrassed anyways.

Jill says, "Darlin, I'm glad you are happy and growing in confidence. Stop by any time and tell me how you found using and playing with all these things. In fact come by dressed en femme if you wish anytime."

I say, "Oh, um maybe we will see."

The sale is finished, it's a good chunk of cash but I'm so looking forward to trying all this stuff out dressed up as sissy Chantel and as slut Chantel. I give Jill an $20.00 tip for her professionalism and kindness to let me play as such before her. I also want to try all this stuff out at night at the rest area soon.

The drive home was fun as I was horny and once home I dressed up as Chantel in my pink maids dress, white tights, pink 5 inch spike heel pumps, and a wig and makeup. I did not leave the house but I did get into playing with the dildo and try a freezing of water in the ice lock to see how long it takes to melt. I masturbated in my pink maids dress, handled the dildo and even messed around licking it trying out the flavored lubes. It was very exciting for the sissy in me. Thinking about when I will try it all out at the rest are was. I soon could not contain myself and ejaculated into my panty. Future fun how that will go we should soon see.

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Part Two to follow soon