Maria Makes Love to Harold!

I had checked into the hotel where I usually stayed for one of my crossdresser outings. It was early afternoon, and I began my usual routine for getting Maria ready for what I hoped would be an evening's adventure.

I rubbed depilatory crème all over my body from the neck down. I waited until enough time had passed and then hopped in the shower with a loofah sponge to rub all the crème and body hair off. Completely smooth, I ran a hot bath and added musk-scented bubble bath. I soaked with just my nose above water. While in the tub, I shaved twice and douched three times with a musk scented douche. The water had begun to cool so I climbed out and toweled myself dry. I powdered myself from head to toe with a musk scented body powder. I slipped into my prosthetic bodysuit with silicone breasts, vagina and an open bottom.

I had already painted my nails, fingers and toes, with a crimson red metallic polish. I pulled on a pair of sheer to the waist lustrous shiny pantyhose. They were jet black and crotchless. I usually wear garter stockings, but my dress was so short I decided to go with pantyhose. I slipped into a pair of black sequin 4" stiletto heel pumps with an open toe. I then sat down to do my makeup.

I put on my foundation and set it with powder. I decided to go with dramatic evening makeup. I added eyeliner above and below my eyes and drew it out past the outside corner. I used crimson shaded eyeshadows above and just a little below my eyes. I used volumizing mascara to make my lashes really stand out. I finished my makeup with crimson red lip gloss to match my nail polish. I brushed out my shoulder length hair and blew Maria a kiss!

I stood up, spritzed my favorite perfume, Egyptian Musk behind my knees, on my inner thighs, between my breasts, on my throat and behind my ears. I sprayed some on my wrists and rubbed them together.

I slipped into my black strapless sequin mini dress with a floor length narrow side sash. The dress had no back and just covered my pantyhose waistband. It had a deep plunging neckline, my decolletage was on full display. It was cut short and came about three fourths of the way up my thighs; when I sat down, I was going to be showing a lot of leg!

I put on my rhinestone jewelry set which consisted of a 6-row choker necklace, matching 6-row choker bracelets on each wrist, 4" dangle earrings, and five various style rings on different fingers. I deliberately did not wear any ring on the ring finger of my left hand.

I grabbed my black sequin clutch purse, blew myself a kiss in the mirror and headed down to the bar. When I got there, I saw Harold, my usual bartender, confidante, and therapist sitting at the bar. "Hi Harold. Um, I don't mean to be nosy but are you allowed to be sitting at the bar?"

The bartender behind the bar heard me and interjected, "No. He shouldn't be sitting here. If one of the hotel managers walks in and sees him, he's going to get in big trouble."

I smiled at him and turned back to Harold. "Harold, what's going on?"

He turned and I could tell he had been crying. "My wife of twenty-three years asked for a divorce this morning. It came out of nowhere. The divorce papers cited those bullshit 'irreconcilable differences.' I'm still in shock."

I grabbed him by the elbow and said, "You don't need to add employment problems to your personal ones. I'm taking you to a booth where we can talk. I've bent your ear so many times, you've been such a good listener; now it's my turn."

He allowed me to guide him to a booth, I sat him on the inside and then sat next to him. The bartender brought me brandy. I took a sip and nodded for Harold to begin. His story was a little bit rambling, but I just let him talk. He needed to get things off his chest. I listened intently and touched the back of his hand to let him know I was there for him. He cried softly some of the time, the bartender had given him a stack of tissues to wipe his eyes.

He finished and then really looked at me for the first time that day. "Holy shit, Maria. You look so fucking hot. I know I say this all the time but damn, girl, you're smoking tonight!"

I smiled. This was a game we played. Harold was 100% heterosexual but always said if anyone could make him sleep with a crossdresser, it would be me. "Harold, you are so sweet as always but I'm here for you the same way you've always been there for me."

Harold was a little tipsy but had certainly been sober enough to tell me his story. That's why I was more than a little surprised when he put his hand on my thigh, began massaging it, and said, "Maria, I've lied to you all these years. The only reason I never tried to hit on you was because I was married. Now I'm not. Will you take me upstairs and show me what I've been missing all this time?"

Harold's hand rubbing my pantyhose covered thigh felt amazing. I moaned but then regained my composure. "Harold, you've been a good friend. I am not going to have you wake up tomorrow morning when you're sober and regret sleeping with me. If you're truly serious, we can talk about this at a later date."

Harold leaned over and whispered in my ear, "I heard you moan. My hand on your thigh turns you on." He continued to rub my thigh with his hand and gently nibbled and licked my ear. "I want you, Maria. I've always wanted you. Take me upstairs, please?"

Harold was turning me on. I knew it. He knew it. I turned to look him in the eyes. "Harold, this is not a good idea, not tonight, not with everything that is going on in your life. Please, please, don't do this. Not right now, not tonight."

In response, Harold leaned in and kissed me, he was letting his tongue play over my lips while he continued to massage my thighs with both hands. I kissed him back and let my fingernails play over the now fully erect bulge in the front of his pants. "Harold, I don't think your managers want you making out in a booth here anymore than they want you drinking at the bar. Let's go upstairs where we can talk in private."

I helped Harold out of the booth, signaled to the bartender to put the drinks on my tab, and walked arm-in-arm with Harold to the elevators. When the doors closed, Harold was all over me again. He was definitely hot for some action. He cupped the cheeks of my ass and pulled me to him forcefully. His lips were pressed against mine and his tongue was inside my mouth, exploring it. The thought of actually fucking Harold after all this time was really turning me on and I pressed back against him and kissed him back just as forcefully. The elevator doors opened, and we hurried to my room.

As soon as we were inside Harold reached for me again, but I pushed him away gently. I reached behind me, unzipped my dress, and let it fall to the floor. I was standing in front of Harold in just my pantyhose, heels, jewelry, and makeup. He wolf-whistled softly. His erection was throbbing against the front of his pants.

"Any fantasies baby? Anything that really turns you on? If we're going to do this, I want it to be special for you!"

Harold blushed beet red. "Maria, this may sound so lame to someone like you, but I would love a hand job. The feeling of a woman's hand around my cock, jerking me off, just sends me over the top. One of the many things my wife never wanted to do for me."

"Baby, NEVER apologize for what turns you on. I'd love to wrap my hands around that gorgeous cock of yours!"

Harold smiled as I walked towards him and began to take all his clothes off. When I was kneeling in front of him and peeled his underwear off, I deliberately did not take him into my mouth. Instead, I just kissed the tip of his prick and stood up next to him. We were looking at ourselves in the mirror as we stood side-by-side.

I spit into my hand and began to lubricate his erection. Harold started moaning almost immediately and thrusting into the fingers wrapped around his cock. "Harold! If you feel yourself close to cumming, please let me know. I don't want you spurting all over the hotel carpet. I'll kneel in front of you so I can swallow your love juice."

I had the fingers of one hand wrapped around Harold's hardness. I was jerking him off slowly, then quickly, then slowly, then quickly. I reached underneath him and began to run one of my painted fingernails along his perineum from asshole to scrotum and back again. This was really turning him on, and he began to thrust more furiously into my hand. I leaned over and began to nibble, bite and tongue his earlobe.

"Maria, shit, Maria, shit, oooooohhhhhh Maria! I'm going to cum, I know I'm going to cum baby!"

I quickly knelt in front of Harold. I continued to masturbate him and finger his asshole gently. His cock was throbbing wildly in my hand, I knew it would only be moments. I placed my lips against just the tip of his cock as he exploded wildly. I was milking him now, squeezing his cock as his love juice poured into my mouth past my eager lips. I continued to jerk him off until he couldn't cum anymore. Harold leaned on my shoulders spent.

I stood up and just held him so we could look at one another in the mirror. "Baby, I know I've always told you what incredible legs you have but your ass is magnificent! Looking at it in the mirror while you jerked me off made me just as excited as the feeling of your hand wrapped around my cock."

"I am SO happy you like what you're seeing and feeling, Harold. This night is all about YOU. I owe you so much for letting me spill my heart and soul out to you downstairs at the bar all these years. What would you like to do next, baby?"

"Uuuuummmm, what I would really like is some 69 action! But I'm not gay! I don't mean to insult you baby after that incredible hand job, but I just don't want to see you that way!"

"Harold! I've told you time and again what kind of crossdresser Maria is! I don't want my men to see my maleness. I want them to believe the image of the woman I'm trying to project. Have you ever eaten asshole baby?"

"N-no-noooo. My wife would never allow any of that to happen."

"Eating ass is almost the same as eating pussy, you'll get the hang of it quickly. And I promise you I am squeaky clean back there! Do you want to be on the top or on the bottom?"

"Bottom please, I'll have a better view of your ass and legs."

I laid Harold on his back horizontal to the mirrors so he could watch us. I crawled on top of him slowly, letting my pantyhose covered legs glide across his body as I straddled him. I grabbed his cock and began to lick down the vein until I reached his balls. I took first one, then the other testicle into my mouth. I was kissing and sucking them very gently.

Harold began to kiss my ass cheeks through my pantyhose as he worked his way to my asshole. He very delicately began to tongue my rosebud but became much more enthusiastic when he realized I really was squeaky clean back there. He began to rim me with the tip of his tongue while his hands were massaging my ass cheeks, then thighs, then knees, then calves, then ankles. Of course, this sent me into a frenzy, and I began to suck Harold's cock in earnest.

I deep throated him immediately and began to lick and suck the length of his shaft. Harold was getting turned on as well. He began to kiss, lick, and nip my ass cheeks before he would return to tonguing my asshole. I stopped momentarily, "Stick your tongue inside me baby, tongue fuck my ass!" Then I returned to sucking Harold's cock.

Harold hesitantly began to let the tip of his tongue penetrate me. I moaned against his shaft to let him know how much this turned me on. As he slid his tongue into me deeper and deeper, I was moaning intensely while I continued to suck up and down his erection. I took the fingertip of one hand and began to play with Harold's asshole. I started to slide it inside him gently, this really excited him.

"Oh Maria, oh shit, oh fuck! That is such a fucking turn on. This is so hot. Suck my cock for me baby, I want to cum in that gorgeous mouth of yours!"

Harold began to tongue fuck me. He was thrusting his tongue in and out of my asshole as deeply as he could. I continued to suck him. I was bobbing up and down on his cock, letting my moaning vibrations surround his erection. Harold's hands were all over my ass and legs, I was getting close to an orgasm, I could tell he was too.

"Mmmmmmmmmm, mmmmmmmmmm, mmmmmmmmmmmm!" It felt like I was playing a kazoo as my orgasmic moans traveled up and down the length of Harold's cock. Harold stuck his tongue into me as deeply as he could and was waggling the tip back and forth as he came with me. We continued to eat each other through our orgasms until we were spent.

I collapsed on top of Harold's legs. "Oh, baby, oh Harold, that was wonderful. You're an amazing lover. Oh Harold, I am SO glad I let you talk me into this."

"I can't believe I wouldn't come to your room before this night. Maria, you are so fucking hot. I haven't cum like this in more than twenty years!"

I rolled over so I could lay next to Harold. He held me in his arms. I was nibbling and kissing his earlobe. "Would you like to go for the trifecta, big boy?" I giggled.

"Yes, Maria, oh yes!"

"Still your choice, baby. What position?"

"Doggy style?" Harold asked.

"Of course, baby, I love doggy style. Just wait here, I'll be right back."

I went to the bed and pulled the thick comforter off it. I brought it back and spread it in front of the mirrors. I had also grabbed my edible lubricant from the nightstand. I knelt in front of Harold and began to jerk him off to get him hard again. When he was fully erect and lubricated, I got on my hands and knees facing the mirrors. "I want to see your face when you cum inside me baby! I love watching my man cum for me!"

Harold knelt behind me, pressed against my rosebud and began to slide his cock into me. I was wiggling my ass encouraging him. "Oh yes, that's it, baby. Stick that thing inside me, I want all of it. I want you pounding my pussy with that gorgeous cock. C'mon daddy, give it to me, give it all to me!"

Harold pushed inside me until his thighs were resting against mine. He just held himself there. I began to rotate my hips around his shaft and thrust back against him. He was running his hands all over my pantyhose covered ass and thighs. "Oooooohhhhh, baby, baby, baby! Your hands are so electric, such a turn on. Fuck me, Harold, please fuck me, fuck me now. I want you to fuck me, I need you to fuck me! Ride this pussy, Harold, ride it good!"

Harold didn't need any encouragement. He immediately began to pound my ass, thrusting in and out of me furiously. My silicone breasts were swaying back and forth because of the force Harold was fucking me with. He had this haunted, almost feral look on his face as he was watching himself fuck me in the mirror. I was licking my lips to give him encouragement and let him know how much he excited me.

"Yes, daddy, yes Harold. This pussy is all yours, this pussy is yours any time you want it, this pussy is yours right here, right now. Take this pussy, Harold, take all of it. I want to feel every inch of your cock inside me. Fuck me, Harold, fuck me, Harold, FUCK ME!!!!"

I didn't think it was possible for Harold to fuck me any faster or deeper, but he did. He had his hands cupping my upper thighs pulling me into him on every down stroke. Somehow, he managed to pick up the pace, I felt like I was getting fucked by one of those dildo machines at top speed!

"Oh Maria, I love your pussy, I want to bottom out in your pussy, I want to fuck you all night long! Maria's pussy is so good, it's the best pussy I've ever had. Fuck you, Maria, I'm fucking you Maria, fuck, shit, fuck, shit, fuccckkkkkkkk!!!! Oooohhhhhhhhh, cum, cum, cumming in you Maria!"

Harold exploded in my ass as wave after wave of his hot sperm filled me up. "Rub my ass cheeks, rub my thighs, rub my legs! Harold, I'm close so close!" I continued to ride his cock as Harold's hands were everywhere. "Uh, uuuhhhh, uuuuuuhhhhhhhh! D-Da-Dad-Daddy! Cumming for you baby, make me cum for you baby! Shit, shit, shitttttttttttttttttttttttttttttttttttt!!!!"

The strength of my orgasm caused me to collapse under Harold. He fell on top of me, I could feel his orgasm subsiding as we just lay panting. Somehow, I managed to get us upright and to the bed where we both collapsed.

I held Harold tightly, he began to sob gently and cried himself to sleep in my arms. I rarely let a man spend the night with me, but this was Harold. I had no idea if he had any place he could go to spend the night. I just knew I owed him for all the times he was there to listen to my problems and offer advice. I held him, kissed him, and caressed him. Even though he was sound asleep, I was hopeful he knew someone who cared for him was with him.

I woke up before Harold and made coffee. I put on a robe, so I was much more modest looking than last night. Harold and I sipped our coffee, he never said anything about last night, so I didn't either. He told me I was a good friend, a better friend than he ever knew. We made small talk, and after we each finished our third cup of coffee, he told me he needed to go. He had to work that afternoon and he wanted some time to himself.

I walked him to the door. He kissed me gently on the cheek, looked me right in the eyes, and said, "Thank you, Maria. More than you'll ever know, thank you." I kissed him back on the cheek and he left.

....

I wanted to give Harold some space, so it was a month before I went back to the hotel bar. It wasn't busy and he was smiling and whistling to the background music as I walked up and sat down. "Hey, Maria, it's been too long. Where have you been hiding?" He sounded just like the old Harold.

"Um, you know, here and there. How are you holding up? When do you go to court?"

"Maria! You're never going to believe this. My wife decided not to go through with the divorce. We're in marriage counseling together AND the counselor is also a sex therapist! My wife and I are doing so much better, including in the bedroom! We're both working really hard at making things work together!" Harold was beaming when he told me this.

"Harold, I'm thrilled for you! It sounds like the two of you are going to make this work together. It couldn't happen for a nicer guy than you!"

Neither one of us ever mentioned that night again. I certainly wasn't going to be the one to bring it up. If pretending like nothing ever happened was what Harold needed, I was there for him 100%! I continued to get rooms at the hotel, visit Harold at the bar, and unload my problems on him. He was a great listener, offered occasional advice, and was truly a great friend. It felt like I had almost dreamed the whole evening.... almost! 😊