Crossdresser Meets MILF Neighbour in the Grocery Store

Crossdresser Meets MILF Neighbour in the Grocery Store

Posted on November 14, 2015

I love grocery shopping in the early morning. No crowds so easy parking and I'm able to take more time. The store opened at 8 but I planned to go for 9 and still beat the mob. I found most of the moms that shop usually went around 10.30 or 11.

Anyways, I needed to get ready. I thought about being a little more daring today. Not that I had a lot of hair anyways, but I shaved not just my face, but my pubic area. I used a lot of cream and carefully razored off the few strands from my shaft and balls. My ass area was a bit more difficult, but I managed to shave the few strays. After I showered and dried off, I applied some soothing, slightly lily scented body cream. 

Now to pick out my outfit. I had an entire girl wardrobe and often wore my feminine underthings under my man clothes when I go out. I dress up completely at home but never had the guts to fully dress and go out in public.

I opened my special drawer and pulled out my favourite Victoria Secret black lacie, low-rise, cheekini panties. Small enough to be sexy but big enough to tuck and control my 2-inch flaccid cock. Even if I got a boner, which I often did wearing my girl panties, these panties would be able to control my 4-inch hard man meat. But to be sure, I locked myself into my small metal cock cage. It would prevent any unwanted excitement from showing and would keep my thing pointed down and under.

The weather station said it was going to be a hot and humid one today. It was already 25 degrees Celsius at this time of the morning. Normally I would wear a bra and my forms with some sort of baggy heavier sweatshirt to hide it but I would be dying from the heat. So I decided to go with something lighter went with my new heathered-grapefruit, Lulu Ebb to Street tank. It was kind of close enough to look like a male could wear it. The tight shirt did little to hide my excited pointy nips poking through.

I pulled on a pair of Iris flower coloured Serenity Shorts and then thought, "Wouldn't it be sexy to wear some garters underneath. The hanging straps would dangle on my thighs and be a constant reminder of what I was wearing underneath... Not that I really needed reminding."

I grabbed my black lace garter belt which had three straps dangling from each side. I shortened the straps as much as I could, pushed down my shorts and wrapped the belt around my waist. As I shimmied my bum to pull up my shorts, the straps tickled my thighs. 

I put on some thin white sockettes and tied my low ankle, high heeled sneakers. At home I would have worn something opened toed to show off my painted pink toe nails. And although they aren't the same, the sneakers would at least make me feel like I was actually wearing some high heeled pumps.

"Crap! It's already that late!" I eyed my clock radio. I didn't bother to check myself in the mirror before I grabbed my keys and ran to the car. 

It was just after 9 when I parked in the outside, open lot. There was only a few other cars there, so finding a space was easy. I switched off the engine and that's when I noticed how short these short shorts were. Of course since I was seated, the garter straps hung hidden. 

I grabbed a cart once I was inside the store and started my shopping; veg and fruit to start. I walked over to the seafood area and really didn't see anything I liked so no fish for dinner.

Especially when I'm shopping, I try to practice my girlie walk with one foot in front of the other. With my "high heels" on, my bum stuck out a bit and swayed as I walked. 

"Evan!" I heard and quickly turned to see who called out my name. "Over here!"

I focused in on one of my neighbours whose house was adjacent to mine. "Hi Bobbie." I answered slightly embarrassed and unsure if she had noticed my feminine strut. 

Bobbie was a MILF and yes I would like to fuck her. I may wear women's clothes but I still loved women. She stood about 5'10" in 4-inch stilettos which pushed her firm bum up and out. The tight jean shorts didn't hurt her at all. She had a very curvy body, one that I wished I could have if I were a female. Her dark hair flowed passed her shoulders and over her ample breasts.

"I thought you might be here. I recognised your car in the lot outside and parked beside it." Bobbie smiled. "At least I'll know one side will be safe from being dented in the door by some idiot."

"That's good." I didn't know what to answer as we walked over to the deli cooler. 

There was a huge selection of prepped and sliced meats and cheeses. I bent over and hunted for some cheapo prosciutto. Bobbie was standing behind me and I heard a slight "Gasp!"

I stood up and turned to Bobbie. "Are you okay?

"Yeah, just thought I saw something."

I looked at her curiously as she did to me.

We walked around a bit more, but it seemed odd that Bobbie was always behind me when I bent over. In the meat and poultry cooler there was a packet of chicken thighs way in the back that was the dated the freshest. As I bent and leaned forward, Bobbie moved behind me. I felt her hand on the back of my thigh and reach under the loose leg of my shorts. Then there was a definite tug on one of my garter straps. I stood up quickly. Too quickly and bumped my head on one of the shelves.

I turned to face Bobbie; my mouth agape and cheeks flushed. Bobbie had a grin on her face. One of those cat that got the pigeon grins. 

"No worries, Evan. I won't tell anyone." Bobbie stared at me. "Well I won't tell anyone unless you don't do as I say."

She made us quickly finish our shopping. "Leave your car here."

We sat in her car. "Okay, tell me." Bobbie ordered.

"Uh... Um... I... sometimes like to wear women's clothing." I answered with much trepidation.

"I see." Was all she said in a matter of fact tone.

Bobbie brought her hand to my chest and then pinched my protruding nipple... Hard!

"Are these your?" She demanded.

"Yes, but I had breast forms at home." Why did I tell her that? I couldn't help but blurt it out.

Her hand slipped down and into my short shorts. I felt her hand feel around my panties and between my legs. A firm grip took hold of my caged cock.

"Well, at least you know your place." She laughed as we drove off home.

Now, safely inside the sanctity of my house, I put away my groceries and went to go change. But first, I went to the toilet to pee and pushed down my short shorts and panties. My cock was hard and strained in the confines of the metal cage. It dripped of pre-cum. The gusset of my panties was soaked. The cage made it impossible to stand and pee so I had to sit like a girl to relieve myself. I just finished wiping off the last dribble with some TP and washed my hands when the doorbell rang.

I opened the door and found Bobbie standing there. She barged her way in. "Don't make me wait ever again."

"Yes, I'm sorry for making you wait, Bobbie." I apologised.

"From now on, it is Ms. Roberta to you. Do you understand?"

"Yes, I'm sorry Ms. Roberta." I sheepishly answered. "I understand, Ms. Roberta."

"Good." She smiled. "Well seems like we have a bit of time for fun. Kids are at summer camp and hubbie is away for the month on a contract. Business in Thailand. Good place for him since he likes shemales a lot. But don't worry, I'm keeping you for myself and won't tell him... Unless you want me to."

"No! Please don't tell anyone." I begged. "I would be so embarrassed if anyone found out. I'll do anything if you keep it a secret."

"Anything?" Bobbie demanded. "Anything."

"Yes, anything." I answered unthinking. "Please?"

"Okay, well I'll think about it." Bobbie pretended to ponder. "And besides hubbie likes shemales not crossdressers."

Bobbie stood there with her arms crossed under her heaving bosom. "Hmmm. First take off those and show me what you are wearing underneath."

I hooked my thumbs in the waist band and pushed down my short shorts to my knees.

"Nice panties! Victoria Secret's aren't they. I have a pair just like them." Bobbie grinned. "Now show me your puny pathetic cock."

I pulled the fronts of my panties over my caged cock. 

"Nice. Where is the key?" Bobbie asked. I nodded towards a covered container. She lifted the lid and dangled the key from her finger. "Is this the only one or is there another."

"The only one, Ms. Roberta. I lost the other." I admitted.

She placed the key ring onto the thick gold chain necklace she always wore. Then she reached into her back and pulled out her phone. "To make sure you always do anything I ask you to do..."

"Click... Click... Click...!" Sounded the phone taking photos.

"No, please Ms. Roberta! No...!" I begged still standing there in just my tight tee. My short shorts around my knees and my pretty panties pulled over my caged cock.

"You said you would do anything for me, did you not?" She asked. "Or do I have to start telling everyone? Friends, neighbours, even strangers."

"Yes, Ms. Roberta." I was beaten. "Anything."

"Wait. We need to make sure this is kind of legit at least." She told me. "I want to video you agreeing to obey and do anything I ask. And you will do it freely and willingly of your own accord."

Bobbie held her phone up which was now recording and waited for me to speak.

"I, Evan." I started. "Shall obey and do anything asked of me by Ms. Roberta. I do this freely and willingly of my own accord until such a time where Ms. Roberta releases me from this contract."

"Excellent!" Bobbie smiled. "That is very good, Evan. Hmmm... Evan doesn't sound very girlie. What would you like to be called? I'll let you choose."

I answered immediately. "Eve. I like Eve."

"Ha...ha! Like Summer's Eve. That woman's crappy douche they use to make." Bobbie laughed. "Do they still even make that stuff?"

"Yes, they still do. I use it once a week." I blurted again and thought "What is wrong with me?"

"Figures you're a douche." She smirked. "Do you have other things?" Referring to my attire.

"Yes, Ms. Roberta. I have a complete wardrobe." I replied.

"Good. Go and change into something more... Appropriate. And make sure I'd be happy with it." Bobbie pointed to me to go and change.

I was unsure of what I should change into. I had to change my panties since the ones I had on were soaked with pre-cum. I pulled off my clothes and sat for a minute in my change room, but had to keep the cock cage on since Bobbie now had possession of the only key.

"Of course!" An inspiration hit me. "My new outfit."

I just received my new Vic Secret bra and panties. The panties were black lacy cheekie panties with pink lace criss crossed up the bum and a small bow tied in the front waist. The bra was their new Ring Cutout underwire push up. With my custom breast forms, the black bra pushed up me to almost a D with a nice cleavage displayed.

I wrapped a lacy garter belt around my waist. It didn't go with my bra and panties but the black seamed stockings that I slid on was a no-no without garters in my view. And stay-ups just never stay up if you know what I mean.

I fixed my face with some light cheek blush, eye blush, liner and mascara which matched the pink pearl lipstick and liner I selected. 

"What to wear...What to wear?" I looked in my closet. "Ah! Perfect... I hope."

I picked out my pink summer dress with five big buttons down the front. I rehemmed it before so the bottom was short and about 8 inches above my knees. I left the top three buttons undone to show off my bra and boobs. A matched set of strappy four and half inch high heels were perfect and showed off my previously hidden painted toe nails.

This time I checked myself in the mirror and made sure everything was perfect. 

"Idiot!" I scolded myself. "Hair!"

I choose a medium length, strawberry blond wig. A string of Mikimoto pearls around my neck and another around my left wrist with matching pearl earrings finished everything off.

"Well here goes nothing." I took a deep breath and walked out to see Bobbie.

I found Bobbie sitting on the couch. She had helped herself to some vodka I had in the fridge. From the looks of the bottle, she had finished off a number of shots. 

"Wow, Evan... I mean Eve." Bobbie's eyes popped open. She handed me a half-filled tumbler which I gulped it down. "You look beautiful. Come here and sit beside me."

She poured us each another stiff drink. "Cheers, sweetie."

I shot the glass of clear liquid. My anxious excitement and empty belly didn't help buffer the alcohol that entered my blood stream as if it were shot directly into my veins. My head was swimming.

Bobbie grabbed the back of my neck and pulled me to her lips. Her hard kiss cut my lips against my teeth. I thought I could taste a little iron in my saliva. She bit the side of my neck. One hand groped my breasts as her other hand slide under my dress and up my legs. 

"Ooh! Ms. Roberta, yes!" I moaned. My tiny cock tried its best to burst the confinements of the metal cage. 

Bobbie's hand suddenly grabbed my throat. It squeezed hard enough to make it difficult to breath and swallow. "This is not for your enjoyment. I shall inform you when it is for your pleasure. Do you understand?"

"Yes, Ms. Roberta. I understand." I managed to squeak back a reply.

"Good!" Bobbie smiled. 

She grabbed the front of my dress with both hands and ripped it open. Buttons flew across the room.

"Very nice. Just like a little girlie slut." Bobbie smirked. "On your knees! Pull down my shorts."

I knelt in front of her. I reached up and undid the buttons. I hooked my fingers inside the waist band and started to pull it down. She wore no underwear.

As I pulled it down, my eyes widened. I managed to pull her shorts just below her bum when out popped a cock! A beautiful, 7-inch thick cock. 

I looked up at Bobbie who was grinning from ear to ear. "I told you hubbie loves shemales."

She grabbed her semi-hard dick and slapped it against my face. "Suck it! Make it hard."

It was so beautiful, I would have sucked it without being ordered to do so. I opened my mouth and used my tongue to guide her in. Bobbie grabbed the back of my head and slammed my face into her crotch. She held my nose into her trimmed pubic area. I was surprised that I could swallow her length without choking. 

She thrusted her hips hard into my face. I could feel her cock grow harder in my mouth and push deeper down my throat. It blocked my lungs and I couldn't breathe. I had to push Bobbie away.

"Gasp! Pant! Pant! Pant!" I gasped.

"Eve. How dare your push me away." Bobbie slapped me hard with her now 9-inch erection. "I was going to be kind to you, but now..."

She pushed me on to my back and knelt between my legs. She pulled down my panties to my knees. She pushed my knees to my chest and spread open my ass crack. Without any ceremony or warning, she jammed her big, shemale cock into my hole.

"Eve! It's tight enough but not too much resistance." Bobbie said surprised while pumping her cock in my asshole.

"Yes, Ms. Roberta. I sometimes use my dildo when I am dressed up." I managed to moan. Bobbie's fucking was having a huge effect on my prostate. If she continued I knew she was going to make me cum. "Oh, Ms. Roberta! You're going to make me cum!"

She smiled more and fucked me harder. "You better not! I haven't given you permission."

It didn't matter. I wasn't going to be able to hold on much more. "Oh please, Ms. Roberta! Oh gawd, pleeeeeze!"

Bobbie was slamming her cock inside me now. I could feel it start to pulse; her head back and eyes closed. She was close to cumming too. "Fuck! Fuck! Fuck! You feel so good you little, slut whore!" 

A few more hard thrusts, I started to feel my cum rush up from my balls. 

"Fuck, bitch! Take my cum!" Bobbie started shooting her cum inside my bowels. My cock cage pointed me downwards. My cream spurted out over my balls and down my crack. Bobbie used her cock to shove it into my ass and mix with hers.

After Bobbie finished cumming inside me, she glared at me and sneered. "What did I say? Who controls when you are allowed to enjoy yourself?"

"Ms. Roberta controls me. Only Ms. Roberta can give me permission to enjoy myself." I obediently replied. "Only Ms. Roberta."

"That's right." Robbie was now sitting on my chest. Her large knob of her still hard cock rested against my lips. "Clean me!"

I opened my mouth but was surprised when she shoved it all the way down my throat. I managed to close my lips around her thick shaft as she face fucked me hard. Her balls slapped against my chin.

"Gawd, you're a good cock sucker!" Bobbie panted. "Better than hubbie!"

I couldn't breathe but with all her weight on my face, this time I couldn't pull away. I started to feel faint as Bobbie slammed my face. She was panting harder and harder.

"Yes, you cock slut! That's it! Oh gawd, I'm going to C..U..!" Was all she managed to get out before I felt gobs of cum shoot down my gullet and into my belly.

Even after just cumming inside my ass, I couldn't believe how much more cum came out of her balls. 

"Uuuh! Uuuuh! Uuuuh!" Bobbie grunted. 

Finally her balls were empty and she withdrew herself from my throat.

"Cough! Cough! Gasp! Cough!" I was choking for air.

Finally able to breathe almost normally, I laid there unmoving as Bobbie was squeezing my breast together and was giving herself a boob job. Her hips started rocking faster and faster until unbelievably more sperm spurted out of her piss hole and splashed my face and chest. A true pearl necklace!

Satisfied, Bobbie finally stood up over me and smiled. "I think you'll do fine. You're a fine skanky, cum slut, aren't you?"

I nodded my head in agreement.

Bobbie redressed herself. As she walked out the front door, she told me. "I'll see you later. Be ready."

Story by: grgy56

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