Jim

Turning around, Gerry came back and kissed me while cupping my groin and giving it a squeeze. He led me through the back door and around toward my car. After one more kiss, he suggested, "How about I meet you at Fratellis in about an hour. I need to rinse off the sawdust and change into something a little sexier."

"Okay, but you better not stand me up, or I'll come looking for you."

"No chance of that!" he grinned before imparting one last kiss.

Gerry

You slide into your car and drive off.

I go into the shop, hop in the shower, rinse off the day's sawdust and reapply my makeup. Looking into the mirror, there's a smile on my face that I just can't explain. A happiness that I haven't felt for years. Knowing that I've met someone that can make me happy to be me.

I slide on some tan pantyhose and wiggle into a somewhat tight sweater dress. Put on a pair of heels and feel a tingle in my genitalia and butterflies in my stomach.

Walking across the parking lot to my truck, I realize that I'm going out dressed on a date for the first time. At this point, I'm so excited that my tucked penis is hard and leaking in the gusset of my hose.

Driving to the restaurant seems to take forever as I just can't wait to be next to you again. What has come over me? I think.

I arrive, and you're standing outside waiting for me. I park my truck, and you come to my door and pull it open. You offer me your arm, and I take it greedily as we stroll toward the restaurant door. Once inside, I hear you ask for a quiet table away from the crowd while slipping the host a twenty. He glances down at his seating chart for several seconds before deciding on a table. The host leads us into the back room, which is only used for parties or overflow.

We're given a corner booth, and you lead me around until we settle out of anyone's line of sight. The host excuses himself, and you pull me into an urgent kiss.

Jim

Once we were seated, I had an overwhelming urge to kiss Gerry and did. It got pretty heated and quickly led to my hand moving between his stocking-clad thighs. Keeping an eye open for the waiter, I reached his tucked cock and cradled it like you would a woman's vulva. Rubbing gently, I felt his cock swell. The head was popping out from in between his buttocks, so I caressed it with a single finger.

Gerry moaned into my mouth as our kiss turned a little less impassioned. Fortunately, I spotted our waiter before he saw our 'state of affairs.' Removing my hand briskly, but casually I also broke the kiss and whispered, "Waiter."

Gerry turned just as the waiter approached and handed us two menus and asked, "May I get you lovebirds something to drink?"

We snickered softly at the thought before I ordered a Miller Lite and Gerry asked for soda water with lime. "I'll get your drinks and be back in a few minutes for your food order," the waiter uttered before moving away.

This time it was Gerry that moved in on me. He pressed his face into mine with real need as his hand gripped my hard-on through my jeans. I let my hand slip between his thighs once again. While exploring, I found a significant wet spot all over the gusset of his hose. Either he came from my earlier actions, or he produced a tremendous amount of semen.  

Knowing that the waiter would be back any minute, I pulled back and breathily suggested, "Let's figure out what we want so that he won't have to come back for a while." Gerry reluctantly agreed, and we quickly perused the menu. As we were looking things over, the waiter returned, and we hastily expelled our likes.

Once he was out of sight, we returned to our fervent handling of each other's genitalia. Smearing his pre-cum across his barely tucked cockhead had Gerry quickly approaching his limit. I felt him tense, and the warmth of his cum quickly coated my hand and the back of his dress. I brought what I could get up to our lips, and we shared his nectar.

Gerry

The aftermath of my semi-public orgasm at the hands of my lover left me feeling vulnerable. The word lover rolled around in my mind as our lips lightly grazing back and forth. Jim was still rubbing me gently, and I wished that we were in my bed at that moment. This was almost too much intimacy for a public place. I wanted us to be naked together and to be able to hold him tight.

Jim's hand moved away from my messy crotch as he brought remnants of my cum to our touching lips. We shared my fluids while staring into each other's transfixed eyes. The cum was well removed from Jim's fingers, but we each kept licking them. That quiet closeness slowly gave way to a more passionate feeling as Jim's hand moved away. Our tongues began to duel as the fire started anew.

As I gripped his cock through his jeans, Jim moved his hands to my breasts and began fondling them both. The feeling was new and overwhelming, but it was another step in my feeling like a true woman. Fortunately for both of us, the waiter cleared his throat as he approached from a distance. As we quietly returned to our dining positions, I kept a hand on Jim's crotch.

Our food was left, and our drinks were refilled before the waiter again vanished. Knowing that I had plenty of time now, I moved my face to Jim's crotch and starting nibbling at the outline of his cock. "I want it now, sexy. Open your pants and let me have it," I demanded.

Jim unhurriedly unbuckled his belt and then sluggishly lowered his zipper. Impatient and in heat, I pushed his hands away while gripping his manhood with both of mine. His cock was awash in his own precum, and I used it to stroke him to full strength. With his head purple and swollen, I took him into my mouth. I sucked him greedily and made short work of taking him into my throat.

Jim must have been close when I came earlier, and I quickly got him there again. I heard the restrained moans coming from his tightly closed lips as I clutched his tightening scrotum. Knowing that he was near only fueled my desire as I sped up my bobbing. I heard a muffled growl milliseconds before he pumped three volleys of cum into my mouth. As he slackened in his post-climax bliss, I cleaned him thoroughly before zipping him back up.

Jim

Gerry finished cleaning me before sitting up as I relished the personal contact in such a public setting. Just before he began to eat, I pulled his lips to mine and kissed him. "I'm going to take you home and make love to you all night, sexy." I could see Gerry shudder before wrapping his arms around me and kissing me deeply.

This kiss cooled off, and we got back to eating and talking like two lovers on a regular date. Full from our fabulous meal, I asked Gerry if he'd like some dessert, but he declined.  

"I'd rather just head home and begin our making love," he whispered as the waiter boxed out leftovers. I asked for the check and, upon its arrival, inserted the necessary cash to cover it and the tip. With Gerry's arm in mine, I led him out of the restaurant to his truck. As he slid into the driver's seat, I questioned, "Your place or mine?"

"Mine, if that's okay with you."

"I'll jump into my car and be right behind you."

"And that's where I want you all night," Gerry added with a little giggle.

Gerry

The meal was superb, and the whole night, Jim went out of his way to make me feel like a lady. Now watching him walk to his car, I was hopeful that the spell would remain at least for a little while longer. I am genuinely enjoying this being treated like a woman. I know that I'll have to work a little harder at it now with a boyfriend. Boyfriend, what a funny thing to say, I chuckled to myself. A tingly feeling ran through me as I repeated it to myself.

Hearing a honk, I noticed that Jim was right next to me and ready to go. I whispered it again, boyfriend, and got that same slight tingle. Driving down the road, I felt like a young woman in love. I know it sounds silly, but it was a feeling I'd never thought I'd have and always wanted. Now with a real chance at the kind of relationship that I'd always dreamed of, I was high in the clouds.

With my daydreaming working non-stop, it wasn't long before I was pulling into my driveway. Jim was close behind and scampered over rapidly to aid me in exiting my truck. Taking my hand, Jim helped me out like a lady. Once I was on the ground, I pulled him in for a display kiss. You know, one of those passionate kisses you do to show off to anyone around. I was sure that some of my older nosy neighbors were paying attention, and I wanted them to get an eyeful.

"Would you like me to bend you over the hood and really give them a show?" Jim asked as our lips parted.

"How'd you know?"

"I know a good show-off kiss when I feel it, and that was a whopper!"

Both of us began to laugh as I dragged him into the house. Another kiss away from prying eyes had us both on fire. Slipping back, I offered, "You just sit right here while I go and slip into something more comfortable." As Jim plopped down on the couch, I hurried into the bedroom and stripped of all my clothes.

Once fully nude, I moved to the bathroom for a quick clean and lube. Back into the bedroom, I found my sexiest little gold nightie with see-through lace sides. I slipped it on before pulling on a new pair of nude pantyhose. The final addition was a pair of gold heels that brought everything together. I was as nervous as a teenage girl going to prom and wondered if I could make it through my bedroom door.

As I trembled at the thought of being seen this way and the possible rejection that I might face, I lowered myself onto the bed. I slowly rolled onto my side and then into a ball as the potential horror overwhelmed me.

Jim called out, "Are you ready, Gerry, or do I need to come and find you?"

I lay there frozen in fear, assuming the absolute worst. I couldn't speak nor shake the feeling of dread. Even though went spent the afternoon together and he seemed genuinely interested in me the way I was, I was still petrified. I heard footsteps nearing my bedroom door before hearing the handle turn.

Before opening it, Jim said, "Ready or not, here I come." Pushing the door open, his first words were, "Are you okay?" Jim sidled up behind me and held me tight. He could see the fear in my eyes as soon as he entered the room. We lay there for some time as he held me tight without speaking. It was his quiet confidence that slowly won me over.  

When he felt me begin to relax, Jim whispered, "Stand up for me, sexy. I want to see this hot little outfit of yours before I peel it off one piece at a time. You know that I promised you all-night lovemaking, but we need to get started, if you still want me, that is."

Jim was standing and pulling me to my feet as his words hit me. If I wanted him? What kind of silly question was that? But, of course, he was using reverse psychology on me because he knew what was going on in my head. Once I was standing, he slowly turned me like a doll on a pedestal.  

"Oh, Damn!" He yelled as he saw the see-through lace panel along the side of my nightie.

My confidence shot up immeasurably at that one statement, and I was quickly back. Finishing my spin, I grabbed his face with both hands and placed a monster kiss on him. Jim pulled me in tight and let his hands wander about under the nightie. His first stop was my ass, grabbing both cheeks firmly and kneading them like dough. After that, they moved up my back and held me even tighter to him.

Easing off a little, Jim moved his hands around to my tits and began palming them like they were a woman's. The thumbs came next as they flicked my nipples. With direct contact, they hardened quickly and brought on that tingling sensation again. He lightly pulled and pinched as I faintly moaned into his eager mouth. With all my self-pity forgotten and my libido in high gear, Jim eased me back onto the bed.

As I moved onto my back, Jim began to strip. It was slow and slightly sexy, and he made fun of himself as he proceeded. We both laughed as he made a mockery of the traditional strip club dance. Once naked, he slowly turned to show off his entire body. With my head out of my ass, I realized that he was just as scared as me and in no better shape. But we both looked damn good for our late fifties.

One thing I noticed right away was except for his head, Jim was totally hairless. I would later find out that he shaved every other day. With a sly look in his eyes, Jim climbed onto the bed and lay down on top of me. We kissed tenderly as he held my head in his hands and gently ground his pelvis into mine. As we both heated up, my hands went to his ass and massaged his firm little buttocks.

Jim

Gerry was over his feeling of insecurity and seemed ready for some serious fun. As our bodies rubbed together, it felt very erotic, especially with Gerry's silky smooth stockings. He was rubbing them up and down the backs of my thighs as we ground our crotches together. The kissing was intense as everything continued to heat up.  

Pulling his legs onto my ass, Gerry stealthily removed his heels. With his shoes gone, he pulled his feet onto my ass cheeks and dug in. Our grinding stepped up to a new level, as did the wrestling of our mouths. Suddenly Gerry's hands moved between his legs, and I heard a tearing sound. Then he grasped my cock and moved it to his open pucker.  

I eased inside him, and he moaned noisily. At first, I thought that I may have hurt him, but the look on his face as I backed away was pure lust. He was already cumming with my initial penetration. As he pulled my face back down to his to re-engage our mouths, I started moving inside him. The sound he made continued to increase in volume as he begged, "Don't stop... don't ever stop."

It was a great feeling as he egged me on with his feet. I gradually moved my hands under his nightie and found his erect nipples. I gently flicked them at first and slowly worked my way up to pinching them softly. That only added to his pleasure, and I knew that I loved making him feel this good. Obviously, his dream to have someone make him feel like the woman he was inside, and I wanted to be that person.

I felt myself nearing orgasm and increased my efforts to try and bring him another before I was done. Wrapping my hands around his breasts, I massaged them while still pulling on his nips. I also pushed his legs back further and began to pound his rectum. Gerry's moans were now at the screaming level, and I swear he could feel my orgasm coming. As my cock swelled and my scrotum tightened, he let out one last bellow before pulling his face from mine.

I stopped deep inside as my sperm shot into his upper bowels. We were both panting as I used all my remaining strength to keep from crushing him. As our normal breathing returned, I felt my cock beginning to shrink inside his warm, slick ass. With neither of us wanting it to slip out, Gerry moved his hands to my ass and parted my cheeks. Pulling one hand back, he slipped a finger into my mouth while saying, "Lube, please."

I slobbered generously on his finger before he returned it to my pucker. He slowly worked it inside me, knowing the effect it would have on my retreating pecker. It felt as good as I knew it would, and soon enough, I was back to full strength. As I began moving in his well-lubed hole, Gerry requested, "Do you mind if I take it for a little ride? I've always wanted to try the cowgirl position."

"Not at all," I answered as I slowly withdrew and rolled onto my back.

Once I was in position, Gerry climbed on top and eased my member back into his leaking and gaping pucker. He started off haltingly as he mumbled, "Oh God, this is so goooddd."

My hands moved up underneath his nightie and found his still hard nipples. I rubbed and flicked them as his speed intensified. Gerry's hands were spreading his cheeks forcefully as he tried to get me even deeper. I noticed that his penis was flaccid as he rode me hard but was leaking profusely. Moving one of my hands to it, I rubbed the underside of the head with just my thumb. It was like stroking a large clit, and it was beginning to yield the same result.

Gerry

I was riding a cock like a cowgirl, and it felt amazing. Jim indulged my fantasy, and I never felt more like a woman in my life. Whether we lasted a few days or a few years didn't matter at that moment. I would always be grateful for the way he treated me this day. When he started rubbing the tip of my penis, I could feel the sensations deep within me. This must be what women feel when their partner cares for them so well.

That feeling kept growing, and soon enough, I was on the brink of a completely different kind of climax. It felt more powerful than anything I'd ever experienced, and I rode it to the end. As it took me, I collapsed onto Jim and flopped about like a fish out of water. Shortly thereafter, I realized that I'd actually passed out for a few minutes. But, waking in Jim's arms and lying on top of him felt so natural. I felt truly desired for the first time in my life.

We lay in that position for some time without saying a word. Jim held me tight and wouldn't let me roll off of him for the longest time. As sleep began to creep up on us, I finally moved onto my side. I removed my pantyhose before he slid up tight behind me. Moments later, we were both out cold.

Jim

It was still dark outside when I woke with my stiffy up against Gerry's warm buttocks. He was wiggling his ass against it and slowly working it toward his pucker. I pretended to be asleep as it slowly penetrated his rectum. Once it was inside, I heard a soft sigh while he stayed quite still. After another minute, Gerry pushed back a little. He seemed to be trying to get my cock a little deeper but was having a difficult time.

I let him squirm for a few more minutes before I slowly pushed him onto his belly. Pushing in slowly, there was little resistance. Gerry was still opened up and well lubricated. As my scrotum touched his, he released a quiet growl. I began pumping him in full strokes. Bringing the tip all the way to the rim before plunging hard until our balls slapped together. Gerry's growls were no longer very quiet.

As I started grunting myself, Gerry screamed, "Oh God... I'm cumming! Don't stop, please."

I had no intention of stopping as I ramped up the speed while nearing my own peak. I collapsed onto his warm body as my sperm filled his bowels once again. We were both panting wildly as I ground his buttocks a little more. I seemed to have an unending capacity to stay hard with Gerry and was loving every second. I was truly enjoying the fact that I was able to please him so well.

As I gradually ceased my movement and came to a stop, Gerry rolled us back onto our sides. He lifted his top leg and put it behind mine, pulling me in tight. Once again, we both dozed off.

Gerry

Awakening a second time with Jim tight up against me was another dream come true. I realized that this is all I'd ever wanted. I began dressing at an early age with this goal in mind all along. I wanted to be made love to and treated like a woman my whole life. Now that I had that, I was going to do whatever it would take to keep Jim.

Watching the sunlight spread across the horizon, I felt reborn and ready to start my new life.