After months of ‘sheltering in place’ I began to crave physical human interaction which is a normal reaction to loneliness. Perhaps I was spending too much time in lingerie, makeup and dresses and subconsciously wanted to experience something even more feminine; like having a physical relationship with a man. Did being immersed as Donna for so long kick-start latent desires?

Latent Fantasies & Latent Dreams

I’m retired, single, in my mid 60’s, quarantined and I’m bored. I’ve been cross-dressing since I was 5 and would use crayons and colored pencils to ‘paint’ my nails. Cherry Popsicles were my lipstick. Over the years the quality of my cosmetics and panties has improved vastly.

Many months ago when the quarantine started I began dressing 100% of the time as my alter ego feminine self: ‘Donna’. I shaped and painted my nails, shaved my legs, let my already shaggy hair grow longer and became more proficient with cosmetics. Since I wasn’t going anywhere it seemed like the perfect opportunity to live my fantasies.

Over the weeks and months I used QVC, HSN and my laptop to order a sundress, a very cute jumper, Daisy Duke denim shorts (with a three inch inseam), two push up bras, a pair of girly flip-flops and cosmetics. I used my phone to order pizza and groceries; the pizza delivery boy calls me ‘Miss Johnson’.

Craving physical human interaction

After months of ‘sheltering in place’ I began to crave physical human interaction which is a normal reaction to loneliness. Perhaps I was spending too much time in lingerie, makeup and dresses and subconsciously wanted to experience something even more feminine; like having a physical relationship with a man. Did being immersed as Donna for so long kick-start latent desires?

I began having unsettling but pleasant thoughts and dreams that I’d never had before. At first they involved me, as Donna, flirting with handsome men. Recently my dreams had evolved to me, dressed as a woman, having sex with handsome and virile men; pleasing, mutually pleasurable sex. I was baffled as to why my mind was wandering into areas it had never gone before.

Placing my FIRST home delivery order: my anticipation was high

It was early morning and I was drinking coffee, reading my newspaper and planning my day. As usual I was wearing my bra, garter belt, stockings and French Cut silk panties under my pink satin pajamas; I also wore a matching silk kimono. I had painted my nails, shaved my armpits and legs yesterday so I didn’t need to bother with that today. A delicate gold chain necklace with a hummingbird charm hung from my neck. My ears sported gold stud earrings.

I was craving human interaction and I needed a few quarantine survival essentials so I ordered groceries and supplies to be delivered to my house; a few food items, a couple bottles of wine, Vodka, Sprite, limes, nail polish remover, cotton balls and panty shields. I was enthralled at the prospect of having a visitor (the delivery man). The deliveryman would be an easy target of opportunity for social interaction; it was a perfect ‘two-fer’.

As I placed my order I thought it would be naughty fun to femme up for the human interaction I would be having and flirt with the delivery person; months of being quarantined at home can do that. My mind was beginning to get lost in my femme persona; I prayed that the delivery person would be a man.

My facial makeup took no time at all and looked fine. I had decided on ‘Rose Wine’ lipstick until I remembered it would be covered by my anti-virus mask so I concentrated on eye shadow, eyeliner and mascara. I went for a more dramatic evening look on my eyes in addition to the lippy. I took time to pluck my eyebrows into an acceptable arch. ‘Long lash’ mascara and an eyelash curler added to the feminine image I sought. The process of looking femme makes me feel good.

I discovered I have too many pairs of earrings even for a woman, let alone for a man. Especially for a man whose only recent femme outings were to my backyard privacy deck and the driveway to get the newspaper, I held several earrings up to my ear to get a sense of what would look cutest. Eventually I selected a pair of classic 3 inch gold hoop earrings. I liked the way they caressed my cheeks. I had a momentary twinge of regret for not getting the double piercings I had vowed to get “someday”.

I replaced my kimono with snug floral lavender ‘girly’ leggings. I felt nicely naughty as I pulled them over my stockings and garter belt. A trained eye could see the outline of my garter tabs and straps (and maybe my tucked boy-bulge) showing through my form fitting leggings; their snugness made me feel fashionably slutty.

I slipped my feet into a comfortable pair of black ballet flats. My top was a lace trimmed scoop neck ivory camisole. A new push-up bra with silicon inserts gave lift and definition where I wanted. I decided against wearing a cover-up top; I wanted my pretty cami to be seen by a man.

I put my long hair in a perky high ponytail and secured it with a colorful Scrunchie; I donned my girly pink anti-virus mask. Drop earrings rubbed gently against my cheeks every time I turned my head; a constant reminder of wearing earrings. My day was going well. I hoped the delivery man would notice something special about me even if it was only my earrings or garter tabs.

I had just applied a very restrained amount of my favorite musk perfume and was accessorizing my outfit with several bangle bracelets and disposable black gloves just as the doorbell rang. I left my protective gloves off as I wanted Mr. Delivery to appreciate my pretty painted and shaped fingernails.

My video security door bell showed a handsome young man wearing a protective mask, a company polo shirt with the store name and logo on it. He looked tall, fit and virile! I nervously giggled. My market items were in individual bags within a large cardboard box.

I opened the front door; a clear glass storm door protected me from direct contact with Mr. Delivery (Rob). I stood tall and tried to emphasize my chest for him; heels would have helped. “Very nice, you’re here much sooner than I thought you would be” I said. We stared at each other through the glass for a moment. I found myself responding to Rob in subtle but physical ways. My boy-bulge stirred and my pulse rate increased.

Rob was not subtle about checking me out; in fact he stared. I don’t know what he keyed in on; Pony tail? Boy-bulge? Leggings? He smiled. I know he smiled by the twinkle and gaze of his eyes. He took an extra step closer from the 6-foot social distancing mandate, held up my box of supplies and said, “Send your husband out and I’ll hand these off to him.”

“I’m not married and I don’t have a roommate” I too quickly volunteered. I was startled by my boldness. I had never flirted with a man before; it made my pulse race in anticipation.

Mr. Delivery asked, “Where would you like me to leave your groceries, Miss?”

Not that he could tell but I was smiling broadly inwardly and outwardly. “Here on the porch is fine.” I pointed a manicured finger at a small porch table. I looked for any hint of a wedding band beneath Mr. D’s tight fitting latex gloves. Happily for me he appeared to be ring free!

“OK” he said. My purchases were placed on the table. He turned to leave and stopped. Turning to face me Mr. D said, “I notice that you have a few dead shrubs and a lot of leaves piled up at the base of your walkway. A person could trip. They should be removed.”

Encouraged I replied, “I’ve been meaning to tidy up the area for quite awhile.” My mouth felt dry. After a short pause, as if he was thinking, he said, “My name is Rob. I could stop by and take care of that for you.”

“That’s very thoughtful Rob. I wouldn’t want to impose on you.” I felt a warmness cross my cheeks. I think I was blushing.

Rob replied, “If you’re concerned about social distancing you wouldn’t even need to come outside when I’m cleaning up… unless you wanted to” Rob playfully offered. He took a business card from his wallet and wrote something on the back. He dropped the card into one of my shopping bags and said, “Here’s my phone number, Miss. Call if you need a man… er, I mean handyman. I’m off work on Tuesdays and Wednesdays.”

It was probably an innocent coincident but Rob’s left hand was on his crotch as he made his offer.

I found myself responding to Rob’s presence in subtle but physical ways; my palms and panties were damp. I was glad I was wearing a panty shield. “Thank you, Rob. Please call me Donna. You look very fit. I just may give you a call; I’m sure you could help with whatever a woman needed.”

Rob glanced at my boy-bulge, pulled down his anti-virus mask, flashed me a bright smile and said “I’m very sure I could straighten things out for you Donna and the pile of leaves wouldn’t be a problem either.” Rob put his mask back in place, turned and walked to his van. Before getting into his delivery van Rob looked back at me and waved. I removed my mask, smiled and returned his wave. I was glad he saw me wave goodbye.

I remained at the door and watched Rob drive away. I savored my not so latent feelings and waited for my pulse and crotch to calm before retrieving my groceries from my porch. I hoped that Rob had left more than a phone number on his card; I wanted a message too.

My brain and crotch were filled with the possibilities of being ‘helped’ by Rob. Perhaps it was the prolonged quarantine but I found myself wanting to help Rob in ways I had never helped a man before. My ‘want’ was unexpected but oddly pleasant.

Fantasies and Wet Dreams; my mind and libido wander

While waiting in the doorway for the lump in my leggings to fade I first reached a hand into my bra and then into my panties and confirmed what I expected; my nipples and penis were erect. I closed my eyes and gently stroked a breast; I fantasized that it was Rob touching me. I felt a very pleasant stirring in my panties.

In accord with my recent dreams I envisioned myself reciprocating Rob’s imaginary touches by teasing his nubs with my tongue. I made a mental image of what their texture would be like as I mentally swirled and sucked his manly tits. In my mind we passionately kissed. I could feel his hands exploring me in ways that I dream about. As we kissed I explored him; I could feel his eager firmness in his pants. I’m sure I felt a throb of introduction.

Those mental images combined with my nipple play resulted in me having a spontaneous and substantial hands free tantric orgasm… my penis and prostrate simultaneously convulsed; my knees partially buckled and I ejaculated forcefully into my panties several times; another exquisite squirt quickly followed. My panty liner captured most of my involuntary emissions. That moment, still standing in my doorway, was an unforgettable visceral and erotic moment. I was truly spent as they say.

Wet Dreams: I want more

It was the perfect wet dream; awake and with my eyes closed. I collapsed into a nearby lounge chair and leaned back with eyes still shut and enjoyed a blissful post orgasmic glow. I sat motionless and let my penis become flaccid. Smiling broadly I grabbed a few Kleenex tissues; I scooped and sopped the wetness from my panties.

As I waited for my breathing to normalize I again wondered where and why such erotic thoughts were becoming normal. If today’s vivid climax was so extremely pleasant what would actually being with a man be like? I couldn’t help wondering if Rob was circumcised.

Retrieving my groceries

I regained my composure and slowly stood up. I straightened my bra, tugged my camisole back in place, patted my crotch for wet spots and stepped onto the porch. I retrieved my groceries and Rob’s note.

I brought the box of groceries into the house and placed them on my kitchen table. I desperately wanted to change into clean panties but that could wait. Using my new vodka and orange juice I made myself a hearty Screw Driver and sat at the table. I took a few sips and stared at my box of groceries for a moment before tentatively reaching for Rob’s note. I picked up his card and read it.

I’ve always been curious…bi-curious

On the back of Robs’ business card were his phone number and a short message: “Donna, your boy-bump intrigues me. It shows me see how special you are. I’ve always been curious about girls like you. Call me.”

I re-read Rob’s note several times and, at that moment, I was happier than I had been in many weeks. I smiled and closed my eyes again and let my mind and libido wander. A man had left me a note; a man that knows about boy-bumps wants me to call him.

My first thought was that I needed to order more groceries. It would be an easy excuse that would let this 65 year old cougar see her prey again; I mustn’t scare him away.

My mind began to process the implications of today’s events. A guy wants to meet me! What do I do now? Do we go on a date? A burger drive-thru? Do I wear pants, a skirt or ?? Do I invite him home? What if he won’t let me touch him? What if he wants to touch me!? Is he circumcised! Do I have condoms? What if….’

Fantasies and Day Dreams; I encourage my mind and libido to wander

I took the last swallow of my vodka, rose from my chair and headed to my bedroom for a leisurely masturbation session. Stopping briefly at my dresser mirror I undid my pony tail, shook out my hair and brushed it into a relaxed shoulder length style. Removing my leggings and panties I peeled off the soiled panty liner and dropped it into the trash. I tossed my damp panties and leggings in the direction of the hamper.

Peering into my dresser mirror I reapplied my lipstick. Noticing slack in my stockings I pulled them up, adjusted my garter straps and reset my garter clips. Rob obviously had an effect on me. I watched in the mirror as my penis strained beneath my red garter belt and panties. I reached down and freed it from its confinement.

I grabbed a large towel and spread it on my bed. I shed my camisole and bra to avoid soiling them and to have easier access to myself. Making sure I had Rob’s note and a box of Kleenex I lay down on the towel. My rigid penis was laying on the front of my garter belt and was pointing towards my chin. A drop of preseminal fluid glistened at me.

I was anxious to keep my garter belt clean

I placed a protective hand towel on top of the front panel of my garter belt and under my seeping penis. I was determined to recapture the magical orgasmic moments I had experienced earlier. I put a pillow behind my head and closed my eyes. I inhaled and exhaled deeply several times. Fully relaxed I encouraged my mind to be with Rob again.

I brought my hands to my tits. Both of my nipples were erect. I drew gentle circles around them and fantasized that it was Rob tonguing them. My penis and brain throbbed in lewd anticipation. I resumed my erotic fantasizing.

In my mind

In my mind I was wearing my baby blue floral sundress and Rob and I were embracing as if we had just finished a slow dance. In my mind I began unbuttoning Rob’s shirt as I leaned my cheek against his chest. He had both arms draped over my shoulders; his body heat and subtle aroma were as erotic as I always imagined they would be. My hand slid inside his shirt.

Rob leaned forward and nuzzled my ear before beginning to softly kiss my neck and ear. My hand found his nipple and I began lightly circling it with the pad of my middle finger; it had engorged into a perky pleasure nub. In unspoken ways Rob let me know he liked what I was doing.

My fantasies continued

I unbuttoned Rob’s fourth shirt button, pulled his shirt open and gave his nipple a prolonged kiss. I made sure to leave a bright red lipstick print. I latched on to his nub with my lips and swirled my tongue all around in an effort to please my man. Rob liked this too. He gasped and shuffled his stance to give me better access. I moved my mouth to his other nipple.

While continuing to tease his nipple I brought my open hand to his crotch and confirmed his hardness. Rob moaned his approval when I began to slowly rub his bulge. Rob pried me away from his nipples and began passionately kissing me. I felt Rob’s penis swell and lengthen. I became more aroused.

I led Rob to my bedroom and we were soon lying on my bed; he was on top of me. Rob reached into my sundress and unhooked my bra. He kissed and caressed my small breasts and nipples. I gasped in delight. As we continued to kiss he brought his hand down to my crotch. I arched my back and eagerly raised my sundress out of his way. Ron hooked his thumbs in the waist band of my panties and pulled them off.

I was delirious with pent-up wanton desires; I did a quick emergency un-tuck of my penis and Rob was soon holding my erection. I prayed its wetness would encourage him. As Rob grasped my throbbing penis he softly said, “I like women like you.” The scent of his arousal added to my arousal. Both our needs were obvious and urgent. I soon discovered Rob’s circumcision status and began to quickly unzip his pants; I was desperate for his penis.

In my fantasy: I brought Rob’s seeping penis out of his pants, retracted his foreskin and began hungrily kissing his exposed cockhead. Rob was lustfully licking my penis when we both convulsed with simultaneous orgasms. Massive amounts of sperm covered our lips and faces.

In reality: While immersed in my sex fantasies I began rubbing my nylon covered legs together for the erotic tactile sensations it always gave me. I began to involuntarily squirm and thrust in an effort to more quickly bring on an orgasm.

Time Out!

I had been determined to prolong the amazing mental sexual buildup to the earth shaking orgasm that was imminent. You should never hurry sexual nirvana. My goal was to have another perfect, hands free, wet dream.

It had taken extreme will power to keep from taking the situation into my own hand. I did deep yoga breathing in order to restrain myself but to no avail; I could not delay what my penis desired. The brain and the penis are amazing organs. You need to exercise them both.

Overcome by lust I wrapped my hand around my rigid penis and brought myself to orgasmic release. One spurt forcefully hit my pillow. Gratefully several gushes of warm sperm found my cheeks and open mouth. I lamented that it wasn’t Rob’s sperm.

I lay in bed enjoying my rapture. I fell asleep plotting how to entice Rob; after all he did know about boy-bumps. I realized that I could simply pick up the phone and call him but where is the fun in that? I wanted him to want me.

Setting the trap; placing my second order

I cross-dress because I like to but dressing pretty to attract a man is very different especially if you’re a man; it takes cross-dressing to a new and exciting level.

Plotting and Planning

I would wear a black garter belt and black stockings; maybe a sexy bustier. A pushup bra (with enhancers), a cute satin camisole, hair in a high pony tail, dangling earrings, false eyelashes, glamour makeup and high heel pumps would complete my outfit. ‘Cougar Cute’ would be a fair description.

Scenario one would have me femmed up and wearing only a bath robe over my lingerie. I’d love to see Rob’s face when I dropped my robe and exposed myself and my boy-bump to him.

Scenario two? There was no scenario two at present. I guess I could clip $20 bills to my garter tabs and have one hanging from my bra. I repeated my previously stated goal: I mustn’t scare my prey away.

I reached for my phone.

“Hello, I want to place an order for a loaf of bread.” I was asked if I needed anything else, “Yes, I also need a box of condoms please; ribbed condoms… and a tube of KY jelly.” I paused a moment and added, “I’ll need to have my order brought in to my kitchen. Is Rob on duty?”

The order taker asked, “Is this Donna?”