Caught Out Again and Again Ch. 02

Caught Out Again and Again Ch. 2

It was a cool summer Saturday morning. Actually pretty cold for late August considering the day before was quite warm. A cold front ran through the city after a torrent of rain and the heavy cloud cover kept the sun from warming the air.

My girlfriend Cheryl would always sleep in since she didn't have to leave for work which gave me the time to go to the grocery store. Of course I would need to go appropriately dressed. I picked out some white cotton panties with polka dots. It had a high, lace waistband with a pretty link bow in front. After slipping on some white opaque stockings clipped to my six strap garter belt, pulled up my pretty panties and adjusted my boy junk inside. The bra was a full cup bra with lacy trim. I really wanted to wear my breast forms with them but the double-D's would be too huge to hide.

Reluctantly I covered up with some jeans and a sweat shirt before leaving the apartment for the store. Even with the sweat shirt on, it was pretty cold. I found and pinched my stiff nipples then chuckled to myself. "They are almost as big and hard as my other boobies!"

At the store, I would laugh to myself as I looked at other women's bum and thought. "I bet my panties are sexier than hers."

I took my sweet time promenading up and down the aisles swaying my ass with each step I took. The taut garter straps dug into my thighs as I walked. I checked behind me before I purposefully bent over at the waist to pick up the items I wanted from the bottom shelf; my straps dug in even more. The more I repeated my actions, the harder my cock got. By the time I got to the snack aisle, I was full hard and straining inside my panties. Not being immensely tall (only five-five), I had to stretch a bit to reach the salt reduced bag of crisps. "Why do they always put those bags of chips on the top shelf?"

So the thing with wearing high riding undies and loose fitting jeans is my waistband can easily peek out over the belt line. With my arms are below shoulder height, my shirt covered everything up but reaching high, the bottom rode up and exposed the small of my back and therefore the lacy tops of my pretty panties.

"Oh! Those look sexy!" I heard behind me. I jerked around to see it was Anastasia from down the hall of my apartment. "Do you have others?"

Anastasia was the divorced mother of two teenage kids (he father had custody). The curvaceous, forty something Russian cutie smiled at me. Her high heel shoes made her much taller than her bare foot, six foot height. A broad smile grew across her luscious, red lips as she looked at me with her ice blue eyes.

"Well? Do you have other panties?" Anastasia asked again.

"Uh..." I paused but nothing more came out.

"So, I'm taking it that response as yes." She placed her hand under my shirt and fingered the lace waist. Slowly her hand crept higher. I knew she would find my... "Bra? You're wearing a bra as well as panties?"

I was more concerned with the volume of her voice than being caught out, but I was harder than granite. My knees were shaking. I wanted to escape Anastasia but couldn't move.

Her finger traced my ribcage along the bottom rib of my bra towards the back. "Oh my! A three hook bra. Very nice! Anything else?"

"I... I..." I stuttered. I don't know why I told her but I couldn't help myself. "I'm also wearing stockings and garters."

"Hm... Nice! I didn't realize you were so much of a crossdressing sissy. Does Cheryl know?" I shook my head no. "Well don't worry. I'll keep this our secret. For now at least. We can work something out. Let's finish shopping first."

She grabbed the bag of chips for me and placed it in my cart. It was difficult to walk with my wobbly knees and the foreboding fear in the pit of my stomach. After paying for Anastasia's groceries as well as mine, we drove home in our respective cars. I knew there will be some sort of payback for this; but when.

A number of days later, Cheryl and I enjoyed some dinner and wine at our favourite restaurant. Dinner was followed by our respective favourite desserts: Chocolate soufflé for her, Crème Brule for me.

"Tomorrow..." She started. "I have a couple of meetings downtown. The second one promises to go pretty late and I won't be home for dinner. Maybe back by eight."

"Okay. I'll just have dinner by myself." I pretended disappointed and pouted.

"Aw... Honey. I may have a special surprise for you when I get back." She gave me a sly smile.

The drive back was promising of what waited at home that night. Cheryl placed her hand between my legs and stroked me through my slacks as I drove. She was doing a real good job and I had some troubles concentrating on the road.

Behind closed doors, Cheryl grabbed the back of my head and crushed her lips against mine. My hands found the zipper tab in back of her dress and I pulled it down, letting the dress fall to her feet. The red bra she wore barely managed to control her huge breasts from spilling out. Her red panties rode high on her perfect hips and just big enough to cover her slippery and wet slit. My fingers traced along her garter straps holding up her silky black stockings.

Cheryl undid my tie before unbuttoning my shirt and pants. As she squatted in front of me, she pulled my pants and boy underwear down as well. Cheryl looked up at me and smiled. She pulled my foreskin back a bit before kissing my crown. She licked her luscious pouty lips wet and then closed them around my knob. I felt her tongue swirl over my head. And then Cheryl sounded my urethra with her tongue.

"Oh fuck, Cheryl! That's so fucking hot!" I groaned. "Oh gawd!"

As she took more and more of me into her hot mouth, she used her finger nails to scrape along the crack of my ass. Her head bobbed back and forth. Her finger pushed between my crevasse until it found my asshole. Her sharp nail pushed its way into me and invaded me deeply inside. A second digit joined the first before she started to finger fuck my ass. Both of her fingers felt deeper than ever before. Her talent always took me to the edge but somehow stopped me from cumming no matter how I tried.

"I want you inside me now!" Ordered Cheryl. "Put your cock inside my cunt!"

We didn't bother trying to make it to the bed room. We did it right on the carpet in front of the front door. I slid my bone easily into her dripping pussy. She was so hot, I thought my cock was on fire. Feeling her stocking legs around my waist and her reinforced heels spurring my ass intensified my need to cum.

"Yes! Now! Cum inside me now!" Cheryl demanded of me. "Fill my cunt with your cum!"

"Uh...! Uh...! Uh...! Uuuhhh...!" I grunted with each eruption from my piss hole.

We finally moved to the bed where we cuddled a bit before round two.

I awoke the next morning. Cheryl was already up. I thought about last night and could still feel her phantom fingers inside my hole. I was hard beneath the sheets and stroked it thinking how I always loved when Cheryl finger fucks my ass. I reached beneath me and placed my finger against my asshole.

Cheryl came back into the bedroom from the shower. She smiled at the up and down movement of the bed covers and let the towel wrapped around her body fall to the floor. She cradled her big boobs and pinched her nipples. A hand slipped between her legs and fingered her clit. "This helping, darling?"

I threw off the covers and let her see my masturbation show. "You know what would help!"

"Oh baby! Don't spoil it for tonight." Cheryl stopped suddenly. "Promise! It will be worth the wait!"

I slowed stroked myself as Cheryl dressed for work. She slipped on a bright red, micro-thong; the one I wore the other day. She made a show of pulling the string taut between her beautifully round ass cheeks. The half cup red lace bra let her boobs spill over. The red, black and gold brocade waist cincher had six thick dangling garter straps which she attached to the patterned stockings.

I could have fucked her all day. "Oh. I'm not sure I can wait that long. Come fuck me now!"

She knew I was suffering and just smiled her response as she buttoned up the red silk blouse. She left the top three undone to show just enough cleavage while being business like. Her dark blue power skirt was a little short and the tailored jacket was just tight enough to leave things to the imagination. She slipped on some stiletto heels and inspected herself in the mirror.

"Stay home. Let's fuck!" I begged as I showed her the clear bead of pre-cum I collected on my finger tip.

I watched her hips sway as she seductively walked toward me. She grabbed my hand and sucked the droplet from my finger before pretending to give it a blow job. She leaned over and showed me her cleavage. She pressed her lips to mine. "Too many meetings today. I'll see you tonight. Be home after 8 for sure."

With that she was gone.

I licked my lips and could taste my own pre-cum. It was barely seven. I had more than twelve hours before Cheryl would come home. I decided to go full girl today.

I got out of bed and had a bath using one of Cheryl's bath bombs; the lilac one. As I relaxed in the hot water, I felt for any stray body hairs knowing full well there weren't any. In fact, I only have to shave my face once in a while. The only relevant hair I have is on my head. Even my crotch area is pretty sparse; barely peach fuzz. That said, Cheryl and other women have remarked on my lovely, long, natural eye lashes.

The water had cooled substantially so I got out and dried off. I used some of Cheryl's body lotion and body power; my body felt silky smooth. I pranced to where I had my private stash.

I painted my finger and toes nails a sparkly, candy apple before I sat at Cheryl's table to put on her make-up. I made sure to apply some heavy mascara so my lashes would be more outstandingly long. The lipstick match my nails.

I attached my self-adhering DD boob forms to my chest and played for a few seconds with the extra big, hard nipples before I adjusted them inside my white balcony bra. My boobs were so secure, I could jump on a trampoline and not be concerned.

I guided the white lace cheekie panties up my legs and over my bum. They were tight and gave me a nice and round behind. I attached the white, RHT seamed stockings to the eight straps of my white garter.

Cheryl had dainty feet so we couldn't share her shoes. I only had one pair. A set of four and a half inch stiletto heel slippers with a thin ankle strap. I loved the way my toes showed out the front of the peep toe heels.

Cheryl had a blond wig she once wore for Halloween. It was long and flowing like Farah Fawcett's on Charlie's Angels which was who she dressed as. It wouldn't be the first time I wore it. Nor would it be the first time I wore her perfectly match black pearl earrings, bracelet and necklace.

Unlike Cheryl this morning, I refused to cover up and promenaded around the apartment in my sexy underwear. I loved hearing the click of my heels on the hard wood floor as I took long strides. The garter straps bit into my ass and thighs as I walked. As I passed by the full length mirror in the vestibule, I posed and thought. "I'd fuck me!"

I did a bit of pretend dusting and tidying up. There wasn't a lot to do since I kept the place pretty neat and clean. On line, I'd of course would read the daily Literotica submissions. MicheleNylons and silkstockingslover are a couple of my favourite authors to read. I too have submitted a number of stories; many based on true facts. I have been told that I have a great affinity to write about wearing women's clothing.

I also had the "bad" habit of window shopping for additional wardrobe or toys or items to enhance my collection. There are so many pretty bras and panties; so many cages and remote vibrators. So many things that keep me hard as I viewed the different shopping websites. I fingered my pee hole as my pre-cum soaked through my panties.

My eyes caught the time. "One O'clock!" I had been so entranced, a number of hours had passed by and I didn't even realize it was lunch. My stomach growled an empty protest.

I got up and went to the kitchen. I lifted the loop of my pink pinnie apron over my head, careful not to muss my hair and tied the long, wide ribbons into a big bow in the back. The hem was mid-thigh and low enough to just cover my stocking tops. Of course the back was open and left me exposed. The top part barely covered my boobs and showed a lot of side boob. The flat apron front was spoiled by the bump poking up due to my boner.

I prepped a simple ham and cheddar sandwich which I took with a glass of white to the outside terrace. It was enclosed by frosted glass and with an unblocked vista so I was unafraid of being seen. Afterwards, I took everything inside to clean up. Dish and glass in the dishwasher. Cutting board and knife in the sink.

"What the... Who the hell are you?" I heard a familiar voice behind me. "Where's Geary?"

I froze in place unsure what to do or say or anything.

"Hey you slut! I'm talking to you!" Cheryl restated her command. "Where's Geary?"

I turned slowly on my heels to face my girlfriend. Initially my mouth was open with nothing coming out but an "Uh..."

There was furiousness in her eyes as she shot daggers towards me. Then it hit her. Taken aback. "Geary? Is that you? What... Why..."

"Er. I thought you weren't coming back until late." I tried to change the subject.

"I forgot a file I needed for my meeting this aft and... Wait. Don't change the fucking subject. Why am I explaining this to you?" Cheryl continued. "What are you... Why are you dressed like... like that?!"

"Where do I start?" I thought. Again, I opened my mouth but nothing came out.

"Don't stand there with your mouth open." Cheryl told me angrily. "I've got no time for this now. Just wait until I get back tonight. You better have a good excuse by then."

Cheryl turned and left, slamming the door shut behind her. As horror-stricken and panic-stricken as I was, I was also excited by being caught out. My cock was achingly hard and needed immediate attention. I pulled up the skirt of my apron and pushed my panties down to my thighs. Pre-cum was dripping onto the kitchen floor as my hand wrapped around my shaft. It was harder and thicker than ever before.

I closed my eyes and started to stroke my meat when the front door opened again and Cheryl returned. She saw me standing there jerking off. "Jesus fuck! Have you no shame?"

That was enough to... "Uuuhhh...! Uuuhhh...! Uuuhhh........!"

Spews of hot cum shot out towards my girlfriend and landed on the floor in front of me.

"You're a fucking sicko!" Cheryl spat out as she grabbed the forgotten files and stormed back out the apartment again.