The Trans Ultra Collection Vol 3

by Ursula Lovelace

  In fact, Jake was rather handsome. I knew he was a football star in his youth and a stud at that. The man wasn’t in championship shape but his body was very healthy for his age. He didn’t have the beer gut that plagued most men of his age. I could also understand his sexual urges after becoming a widower.

  “Well, do you agree, Seth?” Jake asked, folding his arms. “Or should I start buying ad space in the classified section of the newspaper?”

  I knew a threat when I heard one. On one hand, Jake was being merciful by providing me a way out. However, he was asking me to fuck him. The most intimate I had ever been with another guy was during my days as a wrestler on the high school team. I knew my landlord was expecting something more affectionate than a headlock.

  I didn’t know why I hadn’t stormed out of the room already. You would think my apartment wasn’t worth the price of losing my dignity. However, there was something appealing about the offer. Jake wasn’t an unattractive man. Hopefully, he was a man of his word as well.

  I exhaled in defeat and said. “Okay… if it means I can still live in my apartment.”

  Jake smiled. “Any second thoughts? I want someone who doesn’t have any doubts about what is required from him.”

  Indeed, sucking cock was asking a lot out of me. Nonetheless, I shook my head. “I’ll do whatever you want.”

  I figured that Jake was old and wouldn’t last long. The whole encounter would probably be over in minutes. I just had to endure a brief moment of humiliation. It was a small price to pay compared to getting kicked out.

  “Good,” Jake said, clasping his hands together. The man stood up from his chair. “Are you ready, Seth?”

  I raised any eyebrow. “Right now?”

  It didn’t look like I could postpone it. It was too late to change my mind. I wondered that was his plan when he said. “I’m too excited to wait. What better time than the present?”

  I figured it was better if we got this strange encounter out of the way. “Let’s get it over with…”

  Chapter 3

  I followed Jake into his late wife’s bedroom. Even after her passing, Jake had kept it in pristine condition. In comparison, the rest of his suite was in need of a good dusting. I had heard from the other tenants that he had kept her room spotless out of love.

  Now, his motives seemed more sinister.

  The bedroom housed a large queen sized bed. It was large enough the both of us. I knew that its heavy oaken frame could withstand whatever Jake had in mind.

  “Let’s give you a new name first,” he said, walking towards the closet. “Something like Seth won’t do for a girl.”

  This was getting stranger by the minute. “A new name?”

  Jake snapped his fingers. “I know. How about Sarah?”

  I thought the whole idea was stupid. It made it seem like we were children playing a game of house. However, I didn’t want to argue the point. “Okay… Sarah it is.”

  I watched as he rummaged through the closest and said. “I wish I had a wig. Then again, your haircut could pass for that of a woman.”

  While I didn’t like to admit it, Jake was right. Along with my facial features, my hair was just the right length to let me pass as a woman. With my money problems, I had allowed it grow and avoided going to the barber for a quick snip.

  For that matter, I didn’t have much body hair. I had shaved my armpits and my facial hair. Even then, I couldn’t grow a moustache for the life of me.

  I watched as Jake brought out clothes and cosmetic products out of the closet. As a red-blooded man, I didn’t have the slightest clue on what to do with makeup. I worked a boring desk job where I didn’t have much human contact. I didn’t have to worry about my appearance.

  Now, Jake filled the bed with clothes and cosmetic products. There was even a padded bra. I imagined that it would billow out my chest so I resembled a woman. He handed me a pair of bra and panties and said. “Strip out of your clothes and put these on.”

  “Seriously?”

  He glared at me. “I wasn’t asking, Sarah.”

  That’s when it struck me.

  He didn’t want me to just dress up as a woman.

  Jake wanted to transform me.

  With the threat of losing my home looming over my head, I obediently undressed and picked up the lingerie. The cool air kissed my skin as I stripped down but I didn’t feel humiliated. The whole scenario was strangely invigorating.

  In any case, I didn’t have any trouble putting on the lingerie. It was surprisingly second nature to me. The panties fit the curves of my ass and hips as if they had been custom tailored. As for the bra, I found its fabric to be smooth. The padding was form fitting and gave me the illusion of a bust line.

  I couldn’t help but be impressed. “Hey, this actually fits…”

  Jake chuckled and took out a roll of lipstick. “Good, I knew that you were her size. Now, it’s my turn. Sit on the bed, Sarah.”

  It turned out that my landlord was handy with women’s makeup. That begged the question about how much experience he had having men dress up as women for him. I knew I wasn’t the first and I certainly wouldn’t be the last.

  Regardless, Jake knew his way around women’s cosmetics. I couldn’t tell the difference between lip gloss and eyeshadow. Sometimes, I put on a coat of Chap Stick before a date but that was it. Thankfully, my landlord made up for my deficiency with women’s makeup.

  He knew just knew what to apply and the right amount to use. Glancing into the closet door’s body mirror, I slowly saw myself transform into a woman. I had never been the manly type to begin with. Now, I could pass for the fairer sex.

  With a bit of mascara, I stopped passing for a woman and started looking like a real beauty. Before my eyes looked dull and pallid. Now, they were awash with color. A dab of blush brought out the fullness of my cheeks. It was all starting to come together.

  Jake then brought out a dress. It felt unnecessary since I’d have to undress for the main act. However, I didn’t argue that point.

  In fact, I took an immediate liking to his wife’s old dress. It was a tasteful one-piece silk dress. Its fabric was soft and felt form-fitting. It made me feel like I was still wearing only lingerie.

  My landlord added some sex appeal to my look by handing me a pair of stockings. The jet black material highlighted my calves when I put them on. They were tight but not enough to be uncomfortable.

  Finally, Jake handed me his late wife’s jewelry collection. “Are you sure? They belonged to your wife.”

  He gave me a pair of earrings. “It’s not like anyone is using them.”

  As luck would have it, my ears were pierced. My wild days at college were finally paying dividends. I didn’t have any trouble putting the earrings on. A nice pearl necklace soon followed. It made my neck look elegant like that of a waterfowl.

  Finally, it came time for the shoes. Jake picked out a set of high heels that looked to be my size. I wasn’t a particularly tall man so they added to my height. It was strange strutting around in them but I got used to them over time.

  I nearly gasped when I saw my reflection in the mirror. I looked like a Goddess. “Wow…”

  Looking proud of his handiwork, Jake agreed. “Believe me when I say that you’re wearing it better than the woman that came before you, Sarah.”

  The man wasn’t exaggerating. I looked like a supermodel with my soft curves and plump lips. When you came down to it, I really didn’t look all the different. Instead, the makeup and clothes had brought out my feminine side. It was shocking what a bit of blush and lipstick could do to my face.

  As a man, I wasn’t exactly an oil painting. Guys thought I didn’t look manly. Women thought my feminine looks were interesting but they never dated me. As Sarah, I was a real showstopper.

  Everything about my body was perfect for being a woman. My slender build went perfectly with my dress. The padded bra gave me a respectable bust line. Makeup highlighted my soft face and bee-stung lips.
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br />   Jake chuckled as I twirled myself before the mirror. “I think it’s time for the main course.”

  I gulped as he led me onto the bed. I sat on it and watched as the man undressed. His chest came into view as he unbuttoned his shirt. I wanted to turn away as he took his clothes off. However, something compelled me to watch him strip down.

  As I saw before, Jake was an attractive man. Sure, he didn’t have the body of a star athlete but there was a certain appeal to the middle-aged man. When he took off his boxers, I saw that his cock was just as long and hard as that of a younger man.

  The sight of his erection aroused me. It was much thicker and longer than mine. Its bulbous tip looked like the head of a battering ram. Underneath were a thick set of balls. I eyed the entire length of his shaft.

  Somehow, I needed to get that monstrosity inside of my ass. In comparison, my cock was rather modest in size. Even when it was fully erect, my shaft wasn’t going to even land me as an extra in a porn movie.

  That’s when I realized that I still wore my new clothing. Jake cleared his throat and said. “If you’re done enjoying my wife’s clothing, then take it off.”

  From the look of impatience on his face, it sounded more like a command than a request. “Of course…”

  I began by stepping out of my dress. The cool air of the room immediately hit my bare skin. I felt my erection stir within my panties. Then, I took off my shoes. When I began to take off my stockings, Jake stopped me. “Leave those on. The rest can go.”

  I nodded and took off my panties. I lifted the elastic of the band and slid them down to my ankles. Then, I stepped out of them.

  It was a blessing in disguise since my cock felt trapped in there. My erection rose up and nearly touched my abdomen. I couldn’t help but feel a bit embarrassed. I had given Jake a clear signal that I was enjoying this.

  I didn’t know I felt this way. Jake had dressed me up as a woman and made me strip back down. Yet, I didn’t feel humiliated. The whole scenario felt casual as if we were undressing some locker room.

  My landlord certainly enjoyed the situation. His eyes drank in the sight of my prick. I felt a shiver down my spine. I didn’t know whether it was fear or anticipation.

  Jake began to stroke his cock and work it to a larger size. His shaft’s girth was large. It emerged from a thick patch of pubic hair. The whole thing looked like a pillar erupting from a dark forest.

  I wondered what it would be like to have him inside of my ass. I had never put so much as finger inside my asshole. I knew I would be tight as a teenage virgin.

  My landlord sat on the bed and patted it. “Let’s begin.”

  Chapter 4

  Hopefully, it would be over quickly and I could go home. Of course, I wasn’t sure where this could lead. Jake was making me have sex with him in exchange for voiding my missing rent payments. He could try to make this into a regular arrangement. In any case, I’d just have to take it one step at a time.

  When I sat on the mattress, Jake reached out to caress my face. “I knew you would be perfect. You had the perfect face. I just had to put you in the perfect dress.”

  I couldn’t remember the last time I received such a compliment. Usually, women ignored me and men teased me. I never considered myself to be attractive until now. However, I didn’t have time to dwell on it since Jake leaned forward and kissed me.

  His lips were warm and inviting. The kiss was sensual as if we had been lovers for years and years. Soon, I stopped being a passive participant and took a more active role in exploring the depths of his mouth.

  Jake demonstrated his skills by suckling my lips and rubbing my cock. In the back of my mind, I knew that he had done this many times before. His lips and fingers were too talented for him to be green at this. I shuddered when I felt his hand brush against the sensitive skin of my erection.

  He played with my cock for what felt like hours. He drew out every motion to tease me more and more. His fingers ran all the way down to the base of my balls before tracing a path back to the tip of my shaft. I knew he was going to milk this arrangement for all that it was worth.

  My landlord took my hand and guided it between his legs. I felt my knuckles brush against his massive erection. My fingers gravitated towards his prick. I instinctively began to stroke the entire length of his shaft.

  What I lacked in experience, I made up with giddiness. Jake was uncircumcised and I loved watching the flap of skin cover and uncover the bulbous head of his cock. He even vocalized his appreciation for my innate talent. “Yes that’s it… you’re doing great!”

  It wasn’t long before Jake was hard as a rock. To show his gratitude, he brought his hand under my bra and pinched my nipples. They were nearly hard as my erection.

  I decided to return the favor by licking his nipples. I was careful not to stop stroking him as I suckled his chest. The muscles in his torso were hard like padded leather. Jake had kept in great shape for a man in his age. He had the experience of an older man and the body of a young man. There was something attractive about the combination.

  I continued to stroke him faster and harder. Jake’s breathing grew louder and ragged. His body heaved from side to side. I knew he wasn’t too far from an orgasm. I needed to get him off before I could go home. A few more strokes and I would be out here…

  Suddenly, Jake pulled my hand away.

  “No, not yet,” he said, gasping for air. From the look on his face, the man had plenty of gas in the tank. “We’ve got other things to do first.”

  I knew he wanted to draw out this encounter. At the same time, I was a little curious about the things he had planned for me. As eager as I was to settle my debts, I hadn’t felt this aroused in years. For now, I just had to play my part.

  Jake stepped off the bed and knelled beside it. He made his way between my legs and pushed my thighs apart. From the look on his face, I knew he wanted to suck my cock.

  My landlord began by rubbing my cock until it was thick as a pillar. Then, he brought his mouth to it and ran his tongue on the underbelly of my shaft. The feel of his tongue against the delicate flesh was absolutely sensational. It was positively electrifying.

  I was no stranger to blowjobs. Of course, a woman was usually giving them to me. None of them could compare to Jake. His mouth was utterly spellbinding. He must have been very experienced because he was sucking me off like a champ.

  His skill made me feel envious for some reason. I had never sucked a cock before but Jake’s innate talent made me wonder if I could ever give such pleasure to another man. Regardless, I loved the feel of his lips around my rock hard shaft. It was much better than being with a college girl who didn’t know what she was doing.

  Jake’s dexterity with his tongue had me shivering with delight. His mouth was big enough to swallow my entire length of my cock. I wasn’t a particularly well-endowed man but I knew that I was hitting the back of his throat. His hand cupped my balls and massaged me. I repressed a shudder when I felt his fingers touch the sensitive sack. Thankfully, the man was gentle enough so as not to hurt me as he fondled my balls.

  I moaned like an unrepentant blasphemer. “Oh my fucking God!”

  I didn’t think I would be on the receiving end of an earth-shattering blowjob when I came to Jake’s apartment. In fact, I didn’t expect this encounter to be so enjoyable. I had come hat in hand to my landlord’s door. I had gone on my knees to beg for a reprieve. In turn, Jake had made me dress up as a woman before giving me a world class round of fellatio.

  Now, I believed that I was getting the better part of the deal.

  Jake was giving me a world class education in sex. Before, I had feared that he would make our sexual encounter into a regular event. Now, I wanted to extend our deal indefinitely.

  Whatever dread I felt about the encounter was gone. Jake knew exactly what he was doing. More importantly, he loved having sex with me. I never thought my cock would get this hard, especially in the mouth of another man.

  Of co
urse, there was the issue of shoving Jake’s cock up my asshole.

  I couldn’t dwell on that thought since my balls grew stiff. There was an unbearable tightness down there as my cock grew unbelievable rigid. I was at the point of no return. I needed to unleash my load. Jake got the message as he brought his hand to the base of my shaft and began to stroke me. He expertly stroked and suckled me in tandem. Whenever my cock emerged from his mouth, he rubbed it with his hand.

  That was just what I needed to light the powder keg. My eyes saw a flash of light before pleasure coursed throughout my body. I started to climax deep into Jake’s throat. The fruits of my passion gushed out of my cock and coated his mouth with my semen. My landlord was completely unaffected by the power of my orgasm as he happily swallowed my load.