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Old Friend of a Friend - Coming of Abby [M32F31][Chastity][Crossdressing][Gentle Femdom] Part 2
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abbigailcd is in Gentle Femdom
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I couldn’t believe what I heard. Ali a sweet innocent looking woman. Gave me a handjob and locked me in chastity. How did she not turn tail and bolt after she saw me. What is her end game? I was dumbstruck. Could this even be real? I do feel the coolness of the wineglasses in my hand. The cold metal of the cage around my member. This cant be a dream.

Ali: What’s the matter Joey? Have you not had your caged locked before by a woman?

Me: I….n….o.. Wha…t…. jus

She starts giggling as I’m trying to find the words to form a sentence.

Ali: Don’t worry about answering. I have a sense you might not be able to answer in coherent manner. Let’s head on upstairs and bring the wine glasses with you.

I nod my head and motioned with my hand for her to lead.

Ali: You first cutie. I want a view of that ass again. I really enjoyed the view as you rode away.

Letting out a sigh I started walking down the hall. Holding the wine glasses and her in tow. Halfway down the hallway I felt her place both hands on my hips. She applies pressure to each side. As if she wanting me to sway them. Then as I took the first step on the stairs, I felt a playful slap on my right ass check. Lifting my left foot onto the next step another slap now on the left cheek. I placed my right foot on the same step as my left.

Me: Ali are you going to slap my ass on each step?

Quickly I felt a harder slap on both cheeks simultaneously. Letting out a ow. She gave me another smack of the same level.

Ali: What did I say to call me? Yes, I am going to give you a slap on each and every step. Each time they will get a little harder. I want to see your ass in a nice shade of pink. I think you can take some spankings. Stop on the landing,

(Groaning) Me: Yes, ma’am.

I take the next step and sure enough she held true to what she was going to do. Every step a smack and by the time I reach the top I was tender. Even though she wasn’t hitting with full force it felt like it. As instructed, I stop on at the landing.

Taking a few steps forward she could stand as well. Feeling her presence directly behind me. Not touching but standing. Her breath against my back. Sending chill down my spine. Reaching around my and placing a hand on both thighs above my knees. Then moving them inwards and up towards the cage. I let out a soft moan of pleasure. Moving her hands back down to the first spot and giving a squeeze. Feeling her hand move the back to my hamstrings. Letting out a whimper thinking she was going to smack my ass again. I don’t think I could have taken another one. I felt her nail trace up and down my backside sending a shiver from my head to the toes.

Ali: You can go into the bedroom place the glasses on the night stand and take a seat on the bed.

Me: Yes, ma’am.

Placing the glasses down I took a seat on the bed next to the glasses. The bed being soft it is still was a little uncomfortable. Shifting my weight on each cheek trying to find a comfortable position. I look up at Ali who was standing in the door way. She had still had the smile on her face.

Me: Ma’am are you enjoying this?

An even larger grin appeared. She walked over to me. Reaching down and grabbing her glass and taking a sip. Then using her foot to motion that I need to spread my leg I did. She took that spot that my knees were occupying. This gave a view from below of her perky b cups and just above them her green eyes looking down at me. Lowering her glass to my lips and tilting it. Holding it until I finished it all. Placing the empty glass down on the nightstand. She moved both hands to my shoulders then the back of my short hair. Rubbing her hands on my head. She let out a pleasurable moan. Returning them back to my shoulders.

Ali: I love the way men look in lingerie. Generally, it was hard to find a guy who was willing to put on my panties or have his own to wear. Then I found you with a decent collection.*Not sure of what to say or do next.

Just absorbing every word, she is saying. When she stops talking, I make an attempt to place my hands on her hips. Wanting to guide her to my bed and letting her have a turn at being the recipient of an orgasm. Just as I was about to touch her, she shoved me onto my back and takes position on my chest. Pinning my arm against the mattress. Unable to move and her just looking into my eyes. Almost as if she is looking into my soul. Feeling her place a foot on each side of my cage and tapping it.

Ali: What were you planning on doing? Did you forget that you were locked?

Me: Yes, ma’am it slipped my mind that I was locked. I was wanting to return the favor from earlier.

Ali: (Giggling) How sweet. I do appreciate the offer and I will take you up on it at a later time. For now, you are going to get changed before I have to leave. I’ve got an early morning tomorrow.

Me: Does this include removing the cage?Ali: The cage will stay on until Wednesday. Would you be able to work leave early and cook dinner? I’m in the mood for some meat. A perfectly cooked steak dinner should suffice. Like the ones you have posted on Instagram

Me: Wednesday?!? A whole 3 days locked??? I've only played with it it during the day.

Ali: Yes, 3 days. You’re a big boy and can handle it can’t you? From the look of things, you could use the 3 days of chastity.Me: Yes ma’am. Do I at least get to pick out what I wear for the rest of tonight?

Ali: Possibly. Go and pick out a bra and panty to wear for the rest of the day. Nothing else, you will just be in them until bedtime.

I make some grumbling noise and nod my head. She rolls off me and lies on her stomach hands under chin and feet up in the air. Getting off the bed I walk over to the dresser opening the top drawer where I have my bra and panties. Looking at them I had a decision to make. Something basic or sexy fun. I recently had gotten into lace thongs but never worn them with my cage. The other panties have plenty of stretch. Holing up a grey seamless thong I show her. Giving me a disapproval look I placed it back in the drawer. Grabbing a pink seamless and showing it.

Ali: Those are not sexy.

Me: Fine, I’ll grab a lace one then.

Ruffling through them I decided on one of the hanky panky thongs, agave green with a cobalt blue band. It’s one of my favorite ones to wear. Showing it to her and nodding in agreement I put it on. Bras being newer to owning I don’t really have that many options. A few sports bras and a blue and white lace bralette. I picked up the bralette and received that nod of approval. Removing my t-shirt and tossing it into the laundry bin Ali got off the bed and walked towards me. Placing her hands on my chest and pressing me against the dresser. Out of nowhere she pinched my nipples and held onto them. I could back up and I really didn’t way to try and pull away.

Me: Ow…ow…ow…What the hell Ali!!

She continues to hold onto them adding a slight twisting motion. Pulling ever so slightly causing that pain and pleasure sensation. Letting go of them she grabs the bralette from my hands. Holding it to my chest and then tilts it so I can get my arm trough the straps. Once it was on, she places one hand on my cage and the other on my chest. Continuing to keep me pressed against the dresser.

Ali: You should be feeling sexy with the entire lace outfit. I do love the look of the cage in lace panties. You might need to get some more of them. That can be a shopping adventure for us. Do you have a scarf?

Starting to blush I point to the closest where I have a few scarfs hanging. Walking over to them she grabs one and walks back over to me. Placing it over my eyes blocking out most of the light. I feel her hand grab my and guide me back to the bed. Pressing softly against my chest she has me lie down.

(Whispering into my ear)

Ali: I’m going to leave now. I would like you stay like this for the next hour. Relax and reflect on what has happened. I’ll set the alarm for you. Once that hour is up send me a text if you truly would like to continue.

Nodding in agreement she gave me one final pinch on my nipples before she left the room and headed down stairs.

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