When the quarantine started, over ten weeks ago, I began dressing 100% of the time as my alter ego feminine self: ‘Donna’. I’m retired, single, in my mid 60’s, a quarantined crossdresser and I’m bored. It’s been more than two months of ‘sheltering in place’ seclusion and I’ve been having unsettling thoughts that I’ve never had before. Maybe that’s normal as you age. What is not normal is I’ve begun wondering what a physical relationship with a man would be like. Maybe it’s a ‘getting old’ phenomenon.

It would help if you gave first “Senior Moments: Dressing Up in the Age of Social Distancing” a quick read to fill in the back story. Here’s a recap for those that would rather not read the first story. Where this new story starts is clearly marked below as “New Story”.

Recap

I was craving physical human interaction which is a normal.

Dreams and thoughts I’d been having for several weeks involve me, as Donna, flirting with men. Recently my dreams began to involve sex; pleasing, mutually pleasurable sex. Maybe I was spending too much time in lingerie, makeup and dresses. My mind was active in areas it had never gone before. I wanted a relationship.

Did being immersed as Donna kick-start latent desires? I was craving human interaction and I needed groceries so I ordered a delivery. The deliveryman would be an easy target of opportunity. It was a perfect ‘two-fer’. I was enthralled at the prospect of having a visitor (the delivery man). I dress because I want to but dressing for a man added to my thrill.

In preparation to placing my order I dressed a bit more boldly by selecting form fitting lavender leggings which I pulled on over my red garter belt and black stockings. A new pushup bra (with enhancers), a cute satin camisole, hair in a high pony tail, dangling earrings and several bracelets completed my outfit. I made a point to not wear any rings. ‘Cougar Cute’ would be a fair description.

A clear glass storm door protected me from direct contact with Mr. Delivery (Rob). We verbally flirted and 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. His gaze lingered on where my boy-bulge was making itself known through my leggings. I think the outline of my garter straps and clips were also discernable.

Rob left my groceries, and a note, on a porch table as is required by social distancing guidelines. Rob offered to return to “help” me. I hoped he left me more than a work phone number with my groceries. I wanted a message too. Does my hope for a message tie in with my erotic thoughts and dreams I’ve been having recently?

Market delivery recap

My items were bagged, and placed in a medium sized cardboard box which was brought to my front door.

Rob: “Send your husband out and I’ll hand these off to him.”
Me: “I’m not married and I don’t have a roommate” I volunteered. I was startled by my boldness. I had never flirted with a man before.
Rob: “Where would you like me to leave these miss?”
Me: “Here on the porch is fine.” I pointed a manicured finger toward a small porch table.
Rob: “My name is Rob.”
Me: “You may call me Donna.” I found myself responding to Rob in subtle but physical ways. My boy-bulge grew and my pulse rate increased.

Rob took a business card from his wallet and wrote something on the back. He dropped the card into one of my shopping bags.

Rob: “Here’s my phone number. Call if you need a man… er, I mean handyman.”
Me: “Thank you, Rob. Perhaps I will.” I found myself wanting to help Rob in ways I had never helped a man before. My palms became damp. I waved goodbye and remained at the door as Rob drive away.

I needed to calm myself before retrieving my groceries from my porch.

(New Story begins here)

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. I hoped that Rob had left more than a phone number on his card.

While waiting in the doorway for the lump in my leggings to fade I reached a hand into my bra and confirmed what I expected; both of my nipples were erect. I closed my eyes and gently stroked them. In accord with my recent dreams I fantasized that it was Rob touching me. I felt a pleasant stirring in my lavender leggings.

I envisioned reciprocating Rob’s 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 could feel his eager firmness begin to swell 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. And then there was yet another exquisite squirt. 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.

It was the perfect wet dream; awake and with my eyes closed. I sat down in a nearby lounge chair with my head back; 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 and tucked them into 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 being with a man be like? I couldn’t help wondering if Rob was circumcised.

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.

On the back of his business card were his phone number and a short message:

“Donna, your pretty leggings let me see how special you are. Your boy-bump intrigues me. 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 and wants me to call him.
One of my first thoughts was that I should order more groceries. It would be an easy excuse that would let this 68 year old cougar see her prey again. But I mustn’t scare him away.

My mind began to process the implications. 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, skirt or ?? Should I buy Spanx? 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….’

I took the last swallow of my vodka, rose from my chair and headed for my bedroom. 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. I continued to think through today’s developments.

Peering into my dresser mirror I swapped my dangling earrings for two inch gold hoops and reapplied my lipstick. Noticing slack in my stockings I pulled them up, adjusted my garter straps and reset my garter clips.

I watched in the mirror as my penis strained beneath my red garter belt. I reached down and freed it from its confinement; Rob obviously had an effect on me. I was anxious to keep my garter belt clean.

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 my nipples. 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 placed a protective wash cloth under my seeping penis and on top of the front panel of my garter belt. I was determined to recapture the magical orgasmic moments I had experienced earlier. I pulled 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.

I was wearing my baby blue floral sundress and Rob and I were embracing as if we had just finished a slow dance. 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.

I unbuttoned his 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 liked this even more so I pressed more firmly and slowly rubbed his bulge through his pants as I toyed with his tit; I felt him swell and lengthen. I became more aroused.

Rob pried me away from his nipples and began passionately kissing me. He reached into my sundress and under my bra. He caressed my breasts and nipples. I gasped in delight. As we continued to kiss he brought his hand down to my crotch. I was softly mewing and eagerly raised my sundress and did a quick emergency untuck. Ron ran his hand over my panty covered penis. I was delirious with pent-up wanton desires.

As I began to unzip his pants Rob hooked his thumbs in the waist band of my panties. In mere moments he would be holding my erection. I prayed its wetness would encourage him. He slid his hand into my panties. 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 very urgent. I soon discovered Rob’s circumcision status.

At this point in my mental wanderings, as I lay on my bed, I froze my thoughts. I did deep yoga breathing in order to restrain myself. I was determined to prolong this earth shaking moment. It took extreme will power to keep from taking the situation into my own hand. My goal was to have another perfect wet dream. You can’t hurry sexual nirvana.

The brain and the penis are amazing organs. You need to exercise them both.

Readers: Be sure to read previously posted “Senior Moments: Dressing Up in the Age of Social Distancing” to see how this Senior Moment came to be. It was posted 4/24/2020nd is, unlike this story, PG rated.

(When Rob saw me I thought my Boy Bump was less noticeable. Apparently not. It made him want us to get together sooner)

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