Walt

Ch. 1 – My first time with Walt

I was 24 at the time of this story, my feminine body maturing nicely. However, my mind and emotions lagged far behind: I believed that people who fucked me must actually be in love with me! And that they would only love me if I was willing to give myself to them. But, since I was having the time of my life sexually, I turned a blind eye to the truth of my situation.

I was in a very tolerant relationship with Miguel and Silve, an older couple. Miguel, a very wealthy Spaniard, took me as he mistress. I lived in one of their apartments and was used quite often by either of them, and, occasionally, by both at the same time. I was also free to take on other lovers if the opportunity arises, as long as I was available when Miguel was in town.

Miguel encouraged my little flings: he wanted to hear every juicy detail. Afterwards, he lived up to his nickname, the Spanish Bull! I would be worn out by the time his visit was over.

One reason Miguel chose me as his mistress was that I didn't look like a lot of the mistresses or younger wives his friends and acquaintances had. I wasn't blonde and I didn't have large breasts. I stand 5ft-6 and am relatively slender. I have small 33B breasts, but my hips are wide enough to keep me from looking boyish. I'm a brunette with green eyes.

Even though I looked so young, I manage to look elegant and sophisticated (and also very desirable) in the expensive gowns he bought. People admiring me openly was a reflection on his good taste and his status!

He also had a good laugh knowing that no one knew I'm transgendered!

The other reason Miguel wanted me was that I look like I'm sixteen or seventeen. He could show off his "young" trophy mistress and not worry about potential rape charges for fucking a minor. Around the apartment I would dress in ways to be Daddy's Girl for him. I usually wore denim shorts that barely covered my bottom. And cropped tee shirts that exposed my jewelled navel. I seldom wore a bra.

Although Silve seemed to like me, I believe she would have been happier had I not been there. However, Miguel had a thick ten inch cock and loved anal sex. Long periods of anal. Silve would allow him to butt fuck her, but she was glad I loved anal. The rest of the time she still wanted him in her bed.

It also bothered her that I looked like a much younger, though shorter, version of her.

Still, they took very good care of me. I had a very generous allowance, an expense account, and paid college tuition on top of that! I also had a small suite of my own inside their apartment. I was free to roam the entire apartment: I only had to let Miguel fuck me in my bedroom.

Miguel, Silve, and I were enjoying a pleasant evening sipping wine and listening to jazz music. I was dancing seductively, trying to get one, or both, to take me to bed.

"Not tonight, Angela", Silve said. "Miguel has an early flight and you and I have a full day tomorrow."

Over an early breakfast, Silve informed me we had an appointment with her lawyer. Then, we were going shopping and run a couple of errands.

"Miguel and I want you set if anything should happen to us. We're setting up a trust fund for you. You shouldn't have to work, if you don't want to. We also added to your college fund. You should be able to finish, and pursue your dreams."

At the lawyer's, I discovered Silve was the wealthier of the two. She owned the building that held our apartment, among other holdings. The trust fund she created for me was extremely generous, and separate from their holdings. I wouldn't have to worry about my welfare when my looks faded.

We ate lunch, then Silve informed me that we were moving to a larger apartment in a building a couple of blocks away. We were having the new apartment totally remodelled. It would take 8-12 weeks. They wanted me to oversee the renovations and update them as needed. She told me I could remodel my rooms any way I wanted. Rosa, their maid servant and cook, would supervise the kitchen work. She would oversee the work on her family's new apartment.

We picked out furnishings for the living room and their bedroom suite. I would get together with the contractor about my suite. We then went to the new apartment to meet the contractor.

Silve introduced me to Walt. Walt had worked for them in the past. Miguel and Silve liked his work and his workmanship. Although not close, they were still friends.

Walt was in his mid-forties; younger than Miguel, but still nearly twice my age. he stood 6-1, maybe 6-2. Handsome, and very fit looking. He was prematurely grey, his face and hands weathered looking. I couldn't take my eyes off him! I was fantasizing about his hands on my body, and his cock up my ass!

I caught Silve and Walt looking at me with amused expressions. I turned red and muttered an apology. Silve and I left and grabbed a coffee and dessert at a little cafe on the ground floor.

"He may be more man than you are used to handling," Silve said, a knowing smile on her face. "You're welcome to try, though. Don't forget, he's a grown man, he might prefer a woman to a "child"."

"Miguel and I will be traveling for a couple of months. We'll be in Europe for our anniversary. I have a flight out later tonight."

When Walt's crew started working, I would come by every day. Walt was very professional. He asked what I wanted since he would work my suite first. He suggested a nice, small study, with a sitting room attached to the bedroom. I would have a very luxurious bath with a shower and a Jacuzzi. I had a little entry way separating my study from the rest of my suite. My suite was going to be a very nice apartment on its own!

I always came over wearing really short denim shorts and a tank top, braless, just like I wore at the other apartment. The crew would look me over and generally ignore me. Walt was very patient, but finally asked I not come around so often, and to wear more clothes when I came back. Silve warned me!

I started coming over twice a week, later in the day. I wore a nice skirt and blouse that made me appear older and more sophisticated. I also would bring some cold beers for the guys. They appreciated it and I could see Walt reappraising me. I would sometimes stay and drink a beer with them.

I would stay and discuss the progress and address any issues that arose. Walt relaxed around me and I enjoyed his company. He was funny and charming. He still ignored my small flirtations, but he didn't brush me off, either.

I listened to suggestions he'd make. We went one Saturday to pick out fixtures and furnishings for my suite. He would store them in the living room until my rooms were ready. We picked out paint and flooring.

After several weeks, my suite was nearing completion. Walt came one Saturday and found me painting my study. I was wearing my tank top and denim shorts. I had some paint in my hair.

I don't know how long he'd been standing and watching me when he asked, "Why are you painting? The crew will paint Monday."

"I wanted to feel like I was a part of this. I'm enjoying this!"

Walt watched as I continued painting, offering occasional suggestions. I listened and kept on working. I wasn't flirting, today. He seemed impressed that I was taking my work so seriously.

He finally took the brush from my hand and laid it down. He then drew me to him and kissed me roughly. I wrapped my arms around his neck and surrendered to him. When he let go, I removed my top. He cupped my small breasts and fondled them gently.

"I wondered if you were a tease. Are you?"

"I've wanted you since I first met you," I replied throatily.

He pulled me back into a kiss then then worked his hand into my shorts. When he reached my small cock, he pulled back in surprise. He looked confused. I finished undressing and let him look me over.

I couldn't read his expression. I thought he already knew! I had never had sex with anyone who hadn't already known I was transsexual! I felt hurt, and rejected. I was ready to run and hide. I was fighting back my tears, fearing what would come next.

"I heard you were transgendered, but you looked very much a woman to me. I'm having a hard time believing this", he said.

"So I guess you're into anal?" He asked.

Relived, I turned around and spread my cheeks. He got the message and stripped.

He removed his shirt, exposing his muscular and very hairy chest. I licked my lips in anticipation. I was floored when he removed his pants. Miguel is ten inches long and almost two inches thick. Walt was easily eleven inches and, at least, two inches across. I wasn't going to get this in my small mouth! And it would hurt like hell in my ass, but I wanted it badly!

Walt mistook my look and reached for his pants.

"No, don't!" I pleaded. "I want you to fuck me!"

He looked doubtful and asked if I could take him.

"I don't know, but I want to try!" I responded and pulled a bottle of lube from my purse.

Walt shoved me against an unpainted wall, my back against his hairy body. He worked three lubed fingers in my ass trying to loosen me. Miguel hadn't fucked me in several weeks: I was tight.

Walt pushed the fat head of his cock against my tight ass hole. I could feel it stretching open to take him in. I cried out in pain when the head slid in. Walt nearly pulled out, but I yelled at him to keep pushing! The pain was greater than anything I'd ever experienced! I could barely catch my breath! I could feel this monster burning its way in filling me like I've never been filled before!

Walt's cocked hit the end of my channel, but he wasn't complete in! As he tried to force more in, he lifted me from the floor! His body held mine against the wall. His rough hair scratched my back. As I relaxed, he started fucking me harder and faster. I was in great pain, but I was also enjoying being so roughly used!

Walt grunted as he emptied his load deep inside me. Holding me tight against him, he stepped away from the wall. I was suspended on his cock, my feet unable to reach the floor! He let me down gently and pulled out.

I reached behind me and scooped up some of his cum. I licked my fingers clean, while looking into his face. I watched his huge cock stiffen again. I knelt before him to suck his cock, but he pushed me away.

"No one's been able to take it in their mouth. You don't have to try."

I turned around and reached behind to spread my cheeks. He took the hint and grabbed my hips, forcing himself in. He fucked me doggy style, the head hitting the end of my channel, causing me to yelp each stroke. He was trying to get all his cock in, but I think he would have to fuck me often to be able to get it all in. He was so deep inside me when he came again, I thought it would come out my mouth. He stayed there until he finished. He fucked a few more strokes then pulled out spent. I lay on the floor and rested a while. I wasn't sure I could stand!

I rolled over and kissed him. "That was great!"

He kissed me and dressed. I managed to get home and shower after he left.

I had a paper due and couldn't get back to the apartment till Thursday afternoon. It was just as well: I hurt for a couple of days and could not comfortably walk or sit. I was wearing a nice, but modest, sundress. I also had some cold beer. While the crew relaxed, I walked into my suite to check progress.

"We'll be through with your suite next Friday. You can move in to it the following Saturday. The kitchen and living room are finished. I'll need another two weeks to finish the master suite."

"I love how my suite looks! I will really enjoy this!"

"Miguel called. He asked me to see if you wanted a separate entrance from the outside hallway, in case you wanted a private entrance. I can add it if you'd like."

I kissed his cheek and said that would be nice.

"Would you like to go out for supper?" He nervously asked.

I grabbed his hand and headed towards the door.

"I'd wondered if I offended you. You haven't been by," Walt said. "I find I miss having you around. You're not what I expected."

"You mean me having a cock?" I teased.

He reddened. "Since I've been around you, I discovered you are a very nice, sweet, and intelligent young lady."

I laughed and held his hand. "I forgot I often come across as empty-headed teenager!"

Walt looked at me strangely. "I really enjoyed the other night, but I'm worried you may be way too young for me. You look seventeen."

"Walt, I'm twenty four! I just act younger because some men seem to like it. I also happen to want sex very often!"

We enjoyed the remainder of supper, telling each other a little of our life histories. He walked my back to my apartment. He kissed me at the door and started away.

"Walt, I really think you should come in and fuck me," I purred. "I'm not wearing panties and I want you inside me, now!"

He picked me up and carried me to my room. I slowly stripped for him. He quickly undressed. I had him sit in my chair and knelt down attempting to suck him. I couldn't take his head into my mouth. I moistened my lips and bobbed on the head like my mouth was an asshole. I would get most the head in and run my tongue across the knob and over the slip. I would suck lightly as I worked my tongue. His moans told me I was on the right track! Each time I tried to take more in my mouth, but he was just too damned big! Walt ran a hand through my hair. I wanted him to come in my mouth. I was going to suck as long as necessary.

After about thirty minutes, he stiffened and tried to force my head further down, then exploded into my hungry mouth. His warm, bitter juices filled my mouth faster than I could swallow! Some spilled last my lips. When he finished coming, I looked into his eyes as I wiped his cum off my face and slowly licked my fingers clean. I made a show of enjoying his cum.

"Damn! That was fantastic! No one has taken the time to suck me like that!"

I had him lay on his back on my bed. I knelt between his legs and spent several minutes licking his balls. I ran my tongue up and down his cock, kissing the head and licking the slit. He moaned softly, encouraging me on. Soon his cock stiffened, ready for me to ride it.

I lubed his cock and straddled him, lining my ass hole up with his bulbous cock head. I eased myself downward, but couldn't get the head in.

"Walt! Grab my hips and pull down hard! Now!"

He pulled down hard and forced several inches into me suddenly.

I screamed, "Oh, damn, damn. It hurts, oh, it hurts! "

Walt looked panicked and started to push me off.

"No, Walt!" I cried. Don't stop! Oh, please, don't stop! Make me take it all! I won't break, I promise!"

He looked doubtful, but pulled me down on his massive cock. I rested a moment before I started riding him. After several minutes the pain started receding. I placed his hands on my breasts. He fondled and squeezed them as I rode and rocked. I was loosening some and able to take a little more into my stretched channel.

"Oh, Walt, you feel soooo good inside me! I could ride you all night!

He relaxed when he saw I was able to take him. I was going to make it last as long as possible. I leaned over to kiss him. He held me close, then rolled us over so he was on top. I wrapped my legs around him as he slowly thrust deep in to my ass.

He filled me so fully that he was rubbing every part of my channel wall. I was soon coming against his hairy stomach. He flinched at little at this but I encouraged him to keep fucking. I managed to come again. His hairy body felt unusual against my skin, but I didn't want him to stop. I heard my clock chime several times before he emptied into me. We snuggled with him still in me.

"Walt, you can stay the night, if you like."

He smiled then snuggled next to my back, his arm over me. He fell asleep, but I luxuriated in the feel of his arm draped over me and of his body next to mine.

Having someone next to me an entire night was something I was growing to like. Maybe, it was a feeling of security. Maybe, it was the post-coitus intimacy. Maybe, I just felt nice having someone wanting to be next to me after the sex was over. Whatever the reason, having someone holding me throughout the night felt right.

Early the next morning, I could feel his cock stiffening against my bottom. I rolled onto my stomach, legs spread wide, and reached behind me spreading my cheeks.

"I don't have classes till noon," I purred. "Think you could be late?"

He entered me and fucked me hard for nearly an hour! I came couple of times before he rolled off. He took a quick shower before he left for work.

Walt ended up staying with me until the renovations were complete. I sucked him many times. We didn't fuck twice a night, or even every night. It was pleasant having someone share my bed. He quit fucking me a couple of weeks before Miguel returned so I could be tight for him.

That brief time with Walt filled an emptiness inside me I wasn't aware I had. We'd both been missing something and seemed to find it with each other. I just didn't know exactly what, yet, only that the emptiness returned when he had to leave.