Elvira

"Does Frankie want to cum now?" I asked, while tickling his small cock with my damp toes.

"Oh, yes please Mistress," was his immediate, but still panting, reply. I watched as my toe ministrations had teased his small cock back into full hard condition and had his hips thrusting in excitement.

"Jerk yourself off, Frankie," I suggested to him, "then you can cum on Mistress' toes," I added.

"Oh, thank you Mistress," he replied while quickly wrapping two fingers around his dick, stroking himself excitedly.

"Cum Frankie, cum for your Mistress, Frankie," I encouraged him. "Cum on Elvira's toes, Frankie. Cum now for your Mistress, Frankie!" With my toes tickling his small cock, I watched as Frankie convulsed on the floor, dribbling his load of white cum onto my toes and feet. "Very nice Frankie, I do hope you enjoyed that," I commented.

"Oh, yes Mistress, I enjoyed that very much," he responded while still panting from the orgasm.

"I'm glad Frankie, because now you've got to clean up the mess, my dear," I said, as I placed my soggy toes up by his mouth for cleaning. "Now lick your mess clean, Frankie," I commanded him firmly.

"Oh, thank you Mistress," he said as his tongue went to work licking his own cum off my feet.

"Thank you, Frankie," I said as he finished cleaning the man-scum from my toes. "This has been very enjoyable, but I must be on to finish the remainder of my rounds tonight," I added. So, I helped Frankie get up, took him into the bath area for a little clean-up, then redressed him back into his wife-beater and boxers, finally depositing him back into bed. "Good night, Frankie," I whispered, as I leaned over to kiss him on the forehead.

"Good night, Mistress Elvira. I'll cherish this night forever," he added, with a huge smile on his face.

So, Mistress Elvira went back on her rounds, serving her clients, but also in pursuit of more debauchery with her favorite people at the senior center. After Frankie, I did have a minor janitorial situation to tend to, (toilet backup) as well as a minor medical issue, (although at the senior center there is no such thing as a 'minor' medical issue) when one of the residents stubbed her toe on the bed frame, resulting a bloody mess that required clean up, and first aid.

Afterward, as I was strolling down the hall, I suddenly heard a high pitched, staccato moan emanating from Donna's room. Donna was new to the center, and not a regular in the late-night masturbator's club. But Donna was a special treat. She was relatively young for a senior center resident, being still in her 60's, thus still possessing much of her good looks. Donna was thin, had great skin, kept her short hair cut in a bob, still with a beautiful chestnut color. She was a true petite, in that she was only about 5 feet tall, thin, tiny breasts, but with a perfectly shaped ass sitting atop her thin legs. I'm not necessarily into girls, but Donna was beautiful. I can only imagine how beautiful she might have been as a young woman.

I knocked gently on her open door, to alert her of my presence, then called out, "Donna, everything OK?"

I heard a rustling of blankets, and her body, then the response, "Yes, I'm OK, just a little tangled up is all."

"Tangled up, can I help you?" I called out as I entered her room to ascertain Donna's predicament.

"Oh, I'm so embarr...," she started, before seeing me in full costume. "Who are you?" she asked with fear in her voice.

"Donna, relax," I said trying to reassure her. It's just me Ellie; it's Halloween, remember," I said quietly while assessing her situation.

"Oh Ellie, I'm so glad it's you," she started. "I am so embarrassed. I seem to have tied myself up and I can't free myself," she said in explanation of the obvious.

Donna was completely naked, her wrists bound together with a silk tie, and knotted to the headboard. Additionally, she was all twisted up in her bed sheets.

Sensing that Donna was caught in the middle of a late-night fantasy, I positioned myself at her bed side, gently caressed her forehead, while asking her to tell me what was going on.

"Well, it's very embarrassing," she started. "But back when my husband was alive, he would tie me up, and do all sorts of dirty things to my body while I was bound and helpless. As I was lying here tonight, I was reliving some of the memories, and thought it might help to tie myself in a little bit of a knot, and maybe play with myself at the same time. But I think I miscalculated the knot, and then you showed up, and I panicked, and well, here I am in this embarrassing predicament," she said, as she sullenly ended her admission.

"Well Donna," I started in response. "I see two options for how your little predicament can end. The first being that 'Ellie' can untie you, help you get dressed, and then put you back into bed for the night... "Or," I offered, "Elvira can keep you bound, then help you relive your memories of the past."

"Oh, would you do that Ellie, I mean Elvira?" she pleaded. "I crave physical contact so bad sometimes," she admitted. "Could you help me out? Please Elvira," she begged so sweetly.

"Of course, I'll help you out," I responded. "That's what Elvira is here for tonight," I added, with a predatory smirk. "While I'm unraveling these bed sheets, why don't you tell me a little about your husband and the games you played," I requested.

"I'd like that," she responded. "With my husband, I was always submissive, and he was the dominant. Nothing crazy, but he almost always took the lead, and I followed whatever path he chose to go down. As our relationship grew, we realized that bondage was a mutual turn-on. He was a rigger by trade, and knew all sorts of rope tricks, and knots, for every occasion. And I liked being tied-up. Just the thought of being helplessly bound, in the presence of another makes my pussy drip like nothing else," she stated, as a matter of fact. "As our relationship evolved, we got more and more wild, mostly me following his lead, but being the wonderful lover he was, he most frequently went down the path that I truly enjoyed. We both loved to dress me up, tie me into tight bondage, then test my endurance with whips, and cattle prods, and clamps, and plugs, and even pee games. My husband was a wonderful photographer as well, and he would photograph me in all sorts of predicaments, usually ending with explosive orgasms, and cum all over my face. These were some of my favorite things," she added, before becoming misty eyed in the process. "I'm just so sad that all of that has ended," she added, clearly with a broken heart.

As she told her story, I unwound her from the bed sheets, to discover my little, lovely Donna had a butt plug up her ass, and a vibrator at the ready. "It looks like the show was right about to start when I interrupted you," I said.

"Well, I was only supposed to have one arm secured, but somehow, I got both bound up, and couldn't free myself when you walked in," she admitted. "I'm really glad you're here Elvira, because I am certain, I would have had to call for help eventually."

"Spread your legs, Donna," I want to see your body," I requested of her. Donna was still a very beautiful woman, even at this late stage of her life. Her skin was still firm and smooth, her eyes clear, her hair and teeth pristine, and her sex drive still in full gear. "You're a stunning woman, Donna," I complemented her, and watched her smile as proud as a peacock. "

"Would you take a few pictures of me Elvira?" she asked, with a pleading smile, nodding her head at the small disposable Kodak camera on her bed stand.

"How will you get these developed?" I asked her concerned for her privacy.

"We have a good friend who has been developing photos of me for years," she explained. "It was always part of my husband's pleasure to share me," she admitted, "and his friend did it for free, because he loved to see my photos," she added, with more than a hint of pride.

"Pose for me Donna; show off like you would for your husband," I directed her.

Donna took to posing like a seasoned professional, smiling seductively in a distressed sort of way. Thrusting her hips, pursing her lips, adding some fear to her coquettish eyes, Donna was good at this, and I was dripping with excitement as I watched her transform from old lady, into a sexy, mature, woman.

"What would your husband do next?" I asked her.

"Usually, he'd rub his dripping cock all over my face, then forcefully fuck my mouth," she added without hesitation. "But you don't have a cock," she lamented.

"No, I don't," I replied initially. "But I do have an 8", jewel handled, dildo, that I am going to fuck you with," I said as I pulled the dildo out of my sash. "Suck this dick and get it wet and sloppy, Donna, and then it's gonna fuck you hard," I promised her as I worked the faux dick between her pouty lips.

"Oh, that's nice," I said, as I backed away to take a photograph of her with the dildo deep in her throat. Donna was a photographer's dream. As soon as the camera came out, so too did her seductive personality. She truly enjoyed showing off for the camera. "You are beautiful, Donna," I complimented her.

"I wuv is," Donna gurggled, with the dick still in her mouth. After I removed the dick to allow her to speak clearly, Donna said, "the thing I miss the most about getting old, is losing my sexuality. I come alive when I can turn people on. As Debbie Harry once sung, 'I want you to want me'. Do you want me, Elvira?" she asked in such an alluring way.

"Oh, I do want you, Donna. You are beautiful," I stammered, almost mesmerized by the mature lady in front of me. "I'm going to leave the plug in your ass, insert my dildo in your pussy, then vibrate your clit till you explode," I advised her. "Then I'm going to sit back in this chair and masturbate myself as I stare at your sexy, orgasmic, bound body."

And that's what we did. Donna's orgasm was explosive, with her once again moaning in her unique high-pitched, staccato, ah, ah, ah, ah, ah, completely through her orgasm until finished. And then I sat back and vibrated my own clit, while staring with desire at the bound, mature beauty in front of me, until overcome by orgasm. Oh fuck, it was good!

Upon completion, I untied Donna, cleaned up the toys and her bed, then helped Donna into some appropriate sleepwear, and tucked her in for the night. As I kissed her forehead good night, she sweetly offered to do this anytime I wanted, and would be happy if I brought a friend with me. Nice, I thought to myself as I departed her room.

After putting myself out of service for the past hour or so, I had to scamper about for the next few hours catching myself up on my rounds of the facility, administrative, and medicinal duties, as well as to refresh myself, as this night was certainly tiring.

But at 3am I was recharged, and as scheduled, I commenced with the required second tour of the resident rooms. My next stop on tour was with Gene. Gene was a fascinating human being and lived an extraordinary life. Broadway actor, and dancer, author of his own autobiography, and a legendary humanitarian fighting against wars, pollution, religious oppression, and sexual discrimination. In his time, he was truly famous, knew many stars, and made many appearances on television, sometimes as an entertainer, other times as a provocateur. Gene was also a crossdresser extraordinaire, and a legendary drag queen.

Generally, around the center, Gene was pleasant and active, but an unremarkable resident. His living space was full of memories, but his life was now quiet and unpretentious. I had heard stories of his alternate-self, Jeanne, and his crossdressing, but had only met Gene during my time at the center. Tonight however, Jeannie was out, and a sight to behold! The only comparison I can make is to the astounding beauty of the ageless Olivia Newton-John. (Rest her soul!)

Jeanne was about 5'-6" tall, but seemingly much taller in her heels. She could not have weighed more than 120 pounds. She was very slender, very fair, and very feminine. Blonde hair, small but unmistakable breasts, tight body, firm ass, and lady-like, clean shaven legs. Tonight, Jeanne was dressed in an elegant, royal blue, satin evening gown, with sexy slit to mid-thigh. Long, blonde hair curled atop her head, full make-up on face and nails, golden jewelry dangling from her ears, neck, and wrists, and elegant 4", gold, strappy, high heels on her feet. Jeannie was radiant!

"Hello," I offered. "I'm Elvira, and I don't think we've ever met before," I continued.

"No, we haven't," she replied. "I'm Jeannie," she said, introducing herself. "I heard you were in the building tonight, so I wanted to greet you, and let you know what a huge fan I am of your work. "And," she added with a beaming smile, "I wanted you to see some of my best work as well."

"Well Jeanne, it is truly a pleasure to meet you finally. And, if I may add, you look stunning tonight," I complimented her with all sincerity.

"Thank you," she responded gracefully. "With age, and the limited opportunity offered by my living situation, Jeannie doesn't get to come out very often, and that truly saddens me," she said wistfully. "But we're both out tonight, and I cannot tell you how happy it makes me that you came by to see me," she added.

"Well," I admitted honestly, "Gene is the most accomplished thespian in the center, and he's always around to greet me during my shifts. So, I did want to stop and let him see my Elvira outfit, although, I am truly happy to see you here tonight."

"Well for sure, I'll tell Gene all about seeing you and how great you look. And," she went on, "you can trust that he is very happy you remembered him," again with a happy smile.

"Excellent," I said. Can you tell me a little about yourself Jeannie?" I asked. "I've never met you, but clearly you are a big part of Gene's life. How did you spend your life?" I asked, to open the conversation, and because I suspected there was something she wanted to say.

"Well, I'd love to tell you about me," she gleefully started. "I rarely get to talk about myself," she added, "so this is just so wonderful. Please sit down and relax, as it is a long story, but I'll try to get through it as quick as possible," she said, still with beaming smile.

"I've been with Gene his entire life, but our heyday was in the 50's and 60's. People like us just weren't accepted back then. There was a thriving underworld of homosexuality, crossdressing, drag shows, etc., but very few were brave enough to bring their alternate sexuality out in the open. When it did happen, it usually didn't go so well, so we kept our alternate selves hidden away. Gene lived his life in public, and I came out only in safe conditions, like when he worked, or in private settings, or certain gatherings of like-minded friends. The world forced us to live backwards," she explained. "Do you know what I mean?" she asked, seeing the befuddled look on my face.

"No, explain that to me Jeanne," I asked.

"Jeannie was the true self." She stated adamantly. "I was the Wizard of Oz. Gene was nothing but the little man behind the curtain. Jeannie was born with Gene's body parts so the only way we could safely live in public was as Gene. To come out as Jeannie, would risk financial, legal, physical, and existential disaster." Jeannie was animated as she told her story, but remained dignified, and graceful throughout.

"When did you realize the conundrum of your lives," I questioned.

"Oh, we knew very young," she replied. "As soon as we knew there were gender differences, we talked about how we were all wrong." Then adding, "we were maybe five or six years old."

"Oh my," I gasped. "How did you talk? I don't understand," I stated.

"As I alluded to earlier, Gene was just the body, Jeannie was the soul," she began, with what might have been the most insightful conversation I have ever had in my entire life. "Gene was a mistake, and we both knew it. When life got difficult, as it certainly did at times, Gene would lock himself in the bedroom, and talk with Jeannie. Initially he'd put on a feminine sweater, or hold a doll while conversing with Jeannie, to help him talk through his misery. As he got older, he'd do more and more dress-up, always wanting to talk to Jeanne while being very feminine, because he knew Jeanne was very feminine," she explained. "Gene was a nothing but a mistake. He was a shell, with no spine, no courage, no heart, or energy. Jeannie was his true self. He needed her to guide him through life," she clarified.

"So, you sat and had actual conversations with each other?" I asked incredulously.

"Well, yes and no," she added, before explaining further. "Early in our lives, Gene would lock himself up alone, and we'd anxiously work through our problems, knowing he was Jeannie in both his head and his heart. It wasn't a case of split personality or any psychological dysfunction," she made clear. "While he certainly verbalized some dialogue at times, it was mostly Gene solving problems the only way he knew how. By allowing his strongest self to work through the problems, he managed to have a very successful, and mostly happy life. And, I will add, I am extremely proud of how Gene handled things. The patience, persistence, and perseverance required to keep our lives separate, yet continually moving forward to achieve our personal objectives was astounding. Gene was a shell, but he was selfless, and relentless in his pursuit of a better life for both of us," she concluded, while beaming that happy smile again. Then quickly adding, "It breaks his heart to this day that he cannot publicly share his success with me."

"Did it ever get easy for the two of you to merge your lives?" I asked, trying not to sound like an interrogator.

"Thankfully, it did," she admitted while exhaling a deep breath. "Age and success helped a lot, but the entertainment industry blessed us emotionally, and provided enough money to live comfortably, and surrounded by people who accepted us. Gene's finding success on Broadway was a God send," she stated. He danced like a woman, he acted like a woman, he had female emotions; that made him uniquely special on Broadway, which is a uniquely special place."

"But Gene never fully came out as a trans woman, did he?" I asked.

"No, never!" she added firmly. "For us, the world never became comfortable enough for that kind of announcement," she stated regretfully. "But life got good," she quickly added. "Broadway was excellent for us," she started. Gene was accepted and allowed to be very feminine in public, and that made us both so happy. Then in the 60's and 70's, he became the most famous and successful drag queen in America, so that allowed us many opportunities for a public life. Reality was always still hidden away in the closet, but with Jeannie out in public so frequently, we found happiness," ending what I thought was a fascinating story.

Then suddenly, a thought occurred to me. "Can I ask a personal question?" I nervously asked Jeannie.

"About sex?" she questioned right back.

"Yes, how did you know?" I asked, returning volley.

"Darling, that's the one question that everyone asks," she stated while laughing.

"OK then," I said, suddenly much more relaxed, and thoroughly fascinated with the story of this complicated person. "How did you handle the sex?" I asked. "Was Gene a homosexual?"

"Elvira, my dear," she started. "Gene was a mistake, and mistakes don't have sex." Gene was totally celibate. Gene just did not have sex with other people. He didn't crave it, he didn't need it, and he ultimately found that life was much simpler once everyone knew he wasn't interested. He wasn't a homosexual, heterosexual, bi-sexual, or any other form of sexual. He was completely asexual. Only Jeannie had sex." she added emphatically.