Who Wears Short Shorts Again?

Who Wears Short Shorts Again?

"Dong! Dong!" The doorbell rang.

"Who could that be at this hour?" I said to myself. 10 in the morning and I am still dressed only in my nightie. I draped a dressing gown over my diaphanous, Victoria Secret, shortie Chantilly Lace Babydoll and panties. By the time I answered the door, no one was there. Even though I was covered, I hid behind the door so no one would see how I was attired. I looked around to see if there was anyone, but...

I found a package and note at the foot of the door.

I had to crack the door open a bit more to retrieve the items then quickly closed the door. Nervously I looked at the note. "Eve."

"Oh Christ! Only Ms. Roberta knows me as Eve." I gasped to myself. I rubbed my sore ass. "It wasn't a dream."

Yesterday, I had dressed in some shorts which turned out to be a little shorter than I thought they were. I had worn some panties underneath which would have been okay, but I also wore a garter belt and had the straps dangling down my legs. My neighbour, Bobbie now Ms. Roberta caught sight of my straps and made me divulge myself.

That was bad enough, but I discovered Bobbie was actually a shemale with a huge cock hanging between her legs. She fucked my ass and filled it with her cum. Then made me clean off her dirty cock with my mouth until she shot another load into my belly.

I continued to read the note.

"Eve. I found this outfit in my daughter's wardrobe. Put it on. I expect you to be properly prepped and included a bottle of your name-sake (LOL). Wear the APPROPRIATE attire underneath. Make-up but no wig. Jewellery and accessories are okay. And wear the highest heels you have and walk to my place by 2. And no overcoat! Ms. Roberta."

I opened the package and out rolled a package of "Summer's Eve" douche.

Bobbie and her husband had two girls. Both were adopted when they were very young. Her husband had a very good, well-paying job and since you really couldn't tell Bobbie was a she-male, I guess they were deemed good parent candidates.

I picked up the outfit and was a bit taken aback by what she would let her 18 year old daughter wear. The shorts were hot pink, tight short shorts. The top was a tight thin tee. There was also a pair of white, opaque, thigh highs. "I can't wear this!" But my cock had already made up its mind as I could feel pre-cum building up.

"Bzzzzz...!" My phone screamed angrily.

It was a text from Bobbie.

"Know you've probably read the note and saw your new outfit. Don't even think of backing out."

"Bzzzzz!" Another message, actually a video. It was me stupidly agreeing to do whatever "Ms. Roberta" wanted me to do.

"Crap!" I muttered to myself. "Maybe I can think of something while I get ready."

I took the douche and went to the bathroom. I stripped and positioned myself down on my back in the shower. I looked directly at my leaky cock, confined in a titanium metal cage.

I took the bottle and reached between my raised, spread legs then inserted the tube inside my hole. The long, smooth, tapered nozzle easily slid in. That felt pretty good and I ended up fucking myself with it a bit. "Shit! Better not." Finally I squeezed the bottle and sprayed the entire liquid contents into me. Reminded me of Ms. Roberta cumming inside me.

"Jezz, that's a lot of liquid! My belly feels so full." I thought to myself as I reluctantly withdrew the nozzle. I stayed there for a few seconds. "Ummm... More than I thought. Now what the hell am I supposed to do?"

I had an ass full of douche and every slight movement caused some of it to leak out. I tried to stick the nozzle back in to plug it, but I could feel the liquid try to spurt out. I ended up with my hand between my legs and my finger plugging my hole as I carefully got up and moved to the toilet. Even so, a lot of it oozed out and ran down my thigh.

I sat on the toilet and released my hold. A torrent poured out from me and splashed into the bowl below. "Aahh..." I sighed as I relaxed my sphincter muscles.

I rinsed myself out a couple of times, but this time stood over the toilet when I filled myself.

I wiped up all the spilled liquid from the floor and took a shower. I used the soapy soap to shave my mostly hairless self. I made sure my face was perfectly smooth and my body was totally hairless and my skin baby soft.

I toweled off and dusted myself with some lightly perfumed talc. I wrapped my gown around me before going to my bedroom. I spotted my clock radio. "12.30 already! I still have to do my nails!"

I sat down at my table and meticulously painted my finger and toe nails. Next, I carefully fixed my face. Mascara, false eye lashes, blush, lip stick and liner. Even though I wouldn't be wearing a wig, my longish boy hair was kind of a short girlie cut. I hooked a fine gold chain strung with a single, Pandora Hope charm around my neck. The matching bracelet was strung with Passion, Trust, Loyalty and Optimism.

I looked at myself with satisfied glee. "I hope Ms. Roberta will be happy... Wait! What the fuck am I thinking?" I had been so busy with prepping myself I didn't think of a way out of my predicament. My eyes started to tear. "No! Don't cry! You'll wreck your make-up!"

"Bzzzzz!" Screamed my phone. The message read "Half an hour. I'll be watching you. Don't disappoint."

Not really sure what else to do, I continued getting dressed. I pulled up a tight, black, lacy thong and tucked my caged cock inside. I selected a black, push up, demi-cup bra and inserted my very realistic, custom, C-sized breast forms. They were made to match my skin colour and even in a decent light, it was difficult to tell they weren't mine.

I pulled the tight tee over my head. Even if Bobbie's daughter was bigger, it would barely fit my body. The hem of the shirt just covered my belly button. The nipples from my forms easily poked through the flimsy material. My deep cleavage on display thanks to the low scoop neck.

I shimmed up the short shorts up my legs and over my bum. Although they were made of stretchy material, I just managed to squeeze into them. They were tight around my hips and very short. So short, my butt cheeks stuck out below. My panty, whale-tail came out of the back. I might just as well been wearing a wide belt.

I pulled on the stockings and selected a pair of black Mary Janes with a 5-inch stiletto heel. But as soon as I stood up, the stockings slide down. I would have to wear garters to hold them up. The only ones that worked with the slightly thicker stockings were the 6-strap, black ones with big pink bows on the front straps. "Well, at least the bows match my short shorts." I noted.

Fully dressed, I inspected myself in front of the mirror. I looked like a teenaged whore. Okay, a sexy teenaged whore.

"Bzzzz!"

"10 min! Don't b l8!"

I couldn't think of a way out and decided to bite the bullet so to speak. The distance from my place to Ms. Roberta's was about 100 yards. At least both our places were mostly enclosed and would only leave me exposed for about 60 yards. As far as I knew, most of the other neighbours would be at work. Vicky would be the only one, I was aware of who worked from home.

I waited at my front door to the last minute. "Here goes!"

I opened the door and peeked out. "Clear." I stepped out and shut the door behind me.

"Clunk!" The auto-door lock.

"Shit! I forgot my key!" I swore. Luckily I had a spare key hidden, but it was around the back. "I'll have to get it later."

I took a number of steps. Walking around the house in these heels was easier than walking on sloped pavement and I could only proceed with careful and slow strides, but each step produced a super-sonic "click" as my heel hit the ground.

At the end of my driveway, I looked around to see if anyone was coming or noticeable. "No one." I proceeded across the street. The uneven pavement made it even more difficult than my sloped driveway. If I hurried too much, I would turn my ankle, fall and be unable to move without assistance.

Exposed to the bright sunlight, I realised how sheer this shirt was. My black bra was clearly visible beneath. Unprotected by the walls of my house, I nervously took slow, deliberate, careful steps. One foot after another. Each step "clicked" against the pavement and echoed up and down the street. The thought of being seen or caught was terrifying yet so exciting. The expansion of my cock restricted by the cage to which Ms. Roberta had my only key leaked pre-cum from my piss hole and into my soaking panties.

I safely reached the edge of Ms. Roberta's isolated driveway. More confidently, I walked up to the door. It was 1.58. I rang the bell and waited.

No answer.

"Should I ring it again and risk Ms. Roberta's wrath?" I looked about. There was no one around. So I decided to wait, but was feeling more and more anxious about being seen.

A minute passed. Then two, and three.

"Vroooom!" A car pulled into the driveway.

I turned to see it was a pizza delivery car. She couldn't have been more than 22 years old as she popped out of the car with a couple of boxes and ran up next to me.

"Pizza for Bobbie?" She asked.

I tried not to look at her, but from the corner of my eyes, I could see her smiling. "Could she tell?"

"Are you Bobbie?" She asked.

Afraid to answer, I shook my head no.

"Did you ring the bell?"

I nodded affirmatively.

We waited. She giggled.

"Well I can't wait much longer." She rang the doorbell again.

This time the door opened almost immediately. "Oh, hi Eve. How long have you been waiting?" Ms. Roberta was smiling. She was fully dressed in a male business suit. "I ordered some pizza for us. Can you stay here and make sure she doesn't leave? I'll have to find some money to pay her."

Without waiting for a response, Ms. Roberta turned and shut the door on us.

"Well, Eve." The girl said. "Love your outfit. Very slutty, whorish look. I couldn't wear something like that but I think you pull it off well!"

After a number of minutes, the door opened. "I'm sorry, but do you take credit cards?" Ms. Roberta asked.

"Of course, but I left the machine in the car." The girl was openly giggling now. "Hang on."

She ran back to the car to retrieve the device. Ms. Roberta did not invite me in so I stood there waiting. My knees quaking at still being exposed as I was.

The girl punched in some numbers then handed it to Ms. Roberta. "Your girlfriend here seems to be a little cold in the hot sun."

"Oh, she's okay, aren't you Eve?" Ms. Roberta replied.

"Well maybe she has to pee, because there is a big wet spot between her legs!" The girl pointed.

"Ha, ha! Could be." Laughed Ms. Roberta as she pretended to fumble with the machine and then her card. "Oh dear! I seemed to have screwed this up a bit."

"Let me see." The girl looked at the device and reset it. She nodded towards me and said "You can only insert it in the hole one way, but I'm sure you already know that."

It seemed to take for hours, but finally Ms. Roberta was able to complete the transaction. "Here's ten cash for your troubles. Maybe we'll see you again. Say good-bye, Eve"

In my best falsetto voice, I squeaked, "Bye!"

"Thanks!" The girl laughed. "Enjoy your pies! Whichever ones you like!"

Ms. Roberta just stood there watching the girl get back into her car. "Wave good-bye, Eve."

I turned and waved until the car had pulled away.

"Well, Eve. Nice of you to show. You look very pretty in my daughter's things but it seems you made a wet spot in her short shorts. That's very bad." Scolded Ms. Roberta as I still stood outside her door. "Maybe I should make you wait outside and think about what you've done."

My knees were trembling so hard, it was difficult to stand up which made more pre-cum leak and the spot even bigger and wetter. "No, please don't let me stay out here. It was embarrassing enough to be seen by that girl. I would die if someone else we knew saw me." I begged.

"Well. Okay, I guess you better come inside now." Ms. Roberta allowed me access to her house. I was directed to the centre of her front living room. Her drapes were wide open on the huge picture windows. Even with the property being enclosed, the fact I was still publicly visible.

Ms. Roberta sat down on the couch with her back to the street. I stood there facing her, waiting for her to say something, but Ms. Roberta remained silent. I was very self-conscience and didn't know what to do with my hands and arms. Nervously, I tried to hide my boob and crotch area not that it did any good. Anyone who walked up the drive would easily see me and how I was attired.

"Hands down by your side." I heard and startled me awake.

Reluctantly, I dropped my hands. My knees shook. It was petrifying, exhilarating and erotic all at the same time. The longer I stood there the more anxious I got. The more anxious I got, the aroused I got. The more aroused I got, the more pre-cum leaked from my aching cock.

By now the dark pink, wet spot was so big, it WAS like I peed my pants.

"Turn. Show me your outfit." Ms. Roberta instructed.

My high heels on the carpeted floor made it difficult for me to spin too quickly. I carefully pivoted on my toes as I displayed myself to Ms. Roberta.

"I like the garters. Nice touch. Very sexy." Ms. Roberta complimented. "Love the pink bows on the straps."

"Thank you, Ms. Roberta." I smiled slightly. "Your daughter's stocking kept falling down when I stood so it was the only solution I could think of. And these were the only ones that would work."

"Your breasts are amazing! They look so real." Ms. Roberta commented. "I think they are as big as mine."

"Thank you again, Ms. Roberta. They were custom made for me. Unfortunately, I must wear a bra for them to remain in place." I said sadly, but added. "But I'm pretty certain they will be acceptable for Ms. Roberta to tit fuck me if she so desires."

Ms. Roberta smiled and spread her legs wide. "Let's find out."

I knelt down between her thighs and I was kind of glad to be out of view. My hands were shaking as I reached for her belt. I undid the buckle and opened her pants. Out popped her beautiful, uncut, hairless cock. It looked bigger and thicker than I remember from before. I held it and rubbed it against my cheek. It felt so nice, so smooth, so soft and yet so hard. This was the first real cock other than my own I had ever touched and desired. Yesterday was so mind spinning, I couldn't really appreciate it.

A bead of clear pre-cum oozed from her pee hole. I looked directly into Ms. Roberta's eyes and then giggled like a silly little girl. I gently pressed my thumb against the bottom underside of the shaft and pushed it upwards forcing more and more clear nectar from her. When I was about to overflow and drip, I greedily lapped it up.

A hand gently pressed against the back of my head. I lowered my mouth slowly, taking in a bit at a time and ensuring it was well lubricated.

"Mmmm." I groaned as it hit the back of my throat. My lips surrounded the base of her shaft. I thought I couldn't take any more but a firm hand and an upward hip thrust proved me wrong. "Ga..aa..agh!" I choked, but it felt so great.

"Oh, my! What a good little cock sucker my Eve is!" Ms. Roberta cooed as she maintained her hold on my head. "Tell me, Eve. How many cocks have you really had?"

I could only shake my head.

"I think you've must had sucked many cocks. You are such a natural." Ms. Roberta released her hold.

"No, Ms. Roberta. Honestly, yours is the first and only cock that I have ever had. In my mouth or in my ass!" I started to tear. "Ms. Roberta's cock is the only one I will ever love."

"Okay, Eve. Don't cry. I believe you, even though it is hard to believe you've never sucked a cock until yesterday." Ms. Roberta patted my head. Then she pushed her pants down her smooth, hairless legs. Now naked from the waist down, "Let's get some meat between those luscious boobies of yours."

I knew I couldn't take off my bra, but when I tried to remove the tight tee, Ms. Roberta stopped me. She lifted my shirt to just under my boobs. I got the idea. I hooked the shirt over her hard cock and positioned it between my soft mounds. As I pressed them together and stroked her up and down, her knob popped up from between my cleavage and hit the bottom of my throat.

"Fuck, Eve. Your tits feel amazing." Ms. Roberta crooned. "Oh, gawd, they're so soft. I can't believe how good they feel!"

Unfamiliar with how to tit fuck someone, I did my best to emulate the last time it was done to me at the strip club I frequented. There, Chelsea with her huge tits often allowed me to get off tit fucking her.

"Okay! Stop! You're going to make me cum too fast, Eve. Your tits just feel too amazing!" Gasped Ms. Roberta. "Stand up!"

By this time, I didn't care if any one saw me. The dark pink spot had grown so large.

Ms. Roberta turned me around. She grabbed the tops of the short shorts and pulled them down around my thighs. "Oooh, naughty girl! Putting your garters over your panties instead of under like all good sluts do."

Ms. Roberta pulled my thong from my ass and pulled me into her lap. My hole was slick from my own pre-cum leakage. Her hard-on pressed against me and slid easily into me.

"Oh, Eve. You're so tight!"

"Oh god, Ms. Roberta! It feels so big! So good!" I cried as I moved my ass up and down her fuck stick.

She pushed me off. "Spread your legs and bend over."

I spread my legs as far as my short shorts allowed and grabbed my ankles. Ms. Roberta moved behind me and stuck her cock back inside my hole. She held my hips and hammered her groin into my spread ass.

I knew anyone could look in and see me being ass fucked but I didn't care. "Yes, Ms. Roberta! Fuck me! Fuck my slut girlie ass!"

My knees were weakening with every one of her thrusts until they could no longer support me. "Forgive me, Ms. Roberta!" I cried as I collapsed to my hands and knees.

Without missing a beat, Ms. Roberta dropped down and rammed her cock back into my ass. I fell to my elbows and clasped my hands together. I dropped my head to the floor and cradled it with my hands.

"I want to see your face as I fuck your slutty ass, Eve. Roll on your back!"

"Yes, Ms. Roberta." I immediately obeyed not wanting this fuck sensation to end yet.

Ms. Roberta pulled my panties to my thighs and brought my legs over her shoulders before inserting her she-man tool inside my gapped hole. My knees were pressed against my chest.

Suddenly, "Hi Bobbie! I'm home from my trip early!"

I looked over to see Ms. Roberta's husband standing in the doorway. He stared at us fucking. Without another word, he was stripped down and behind Ms. Roberta. Through the full length hallway mirror, I watched him aim his hard cock and push it into Ms. Roberta's ass. It was like being fucked in tandem.

"Oh yeah, Hubbie! Put it in! I've missed having you inside my ass!" Groaned Ms. Roberta.

Hubbie's thrusting shoved Ms. Roberta harder and deeper into me. I wouldn't last too much longer.

"Oh, Hubbie! You're going to make me cum inside this slut's ass!" Screamed Ms. Roberta. "Fuck yeah! Make me cum!"

I watched Hubbie thrust his hips hard. His eyes were closed and I could tell, he was close to cumming too.

"Oh, yeah! Fuck! Jezzus! I'm cumming!" Shrieked Ms. Roberta. I felt her inject me with her cum. "Uuuhh! Uuuhh! Uuuuuuhhhh!"

"Me too! Take my cream!" Shouted Hubbie.

I was cumming and tried to scream as well, but when I opened my mouth, nothing came out. Unlike my caged cock where a flood of white cream jettisoned out onto my face and chest.

When everyone had finished ejaculating, we all stayed there panting; Hubbie with his cock inside Ms. Roberta, Ms. Roberta with her cock inside me and me on my back covered in my own cum.