Chapter 2

One Saturday morning in February I got a call and sleepily answered. “Uh, hullo?”

A gravely man’s voice said, “I can do something special for you. I need money to get my car fixed.”

On my alarm clock I saw it was 6:04 in the morning and I had stayed up late the last night.

I asked, “What do you mean? Who is this?”

“It’s Glenda. I hate to ask you for anything, but without a car...”

I’d been paying Glen / Glenda for blowjobs at a gloryhole occasionally for about half a year.

He continued, “I wouldn’t ask, but I need six hundred by Monday.”

I was nervous about discussing it over the phone. “How about I meet you for lunch at that pizza place down the block from your apartment? Noon?”

“Sure. See you then.”

I was happy I could get a few more hours of sleep. At mid-day, we ate our pizza at a table in a corner, quietly discussing things. I asked, “You need six hundred? What were you thinking of doing for that much?”

He whispered, “If you use condoms and lube, I’ll let you do my butt. Two hundred each time?”

I had never even fantasized about doing anal with a woman, much less a man as unattractive as Glenda. Still, I wondered what it would feel like. I figured that since he had given me a lot of happiness with his mouth, it would be worth a try.

“Okay. I’ll go to a pharmacy quick and meet you at your place.”

He said, “Cindy’s at a friend’s house. I don’t mind if you think about somebody else while we do it. Thanks again.” He shook my hand with his much larger one.

I bought lube and condoms at a drugstore and walked up the stairs to his little apartment. He laid on his belly on the mattress and I lubed us up. I tried slowly inserting my dick in his ass, but it would only go in a couple of inches without hurting him too much.

He said, “I think the angle’s wrong. Let’s try it leaning over the couch.”

I put some more lube on us and tried it. I still had to go slowly and carefully, but was able to fit most of my cock in his ass.

“Ungh! That’s not so bad, James. Go slow, but you can try fucking. Slow, okay?”

“Sure. This feels really great! So tight!”

I slowly slid in and out, over and over. I picked up the pace as I got closer to a climax. I closed my eyes and imagined I was doing it with a beautiful redheaded woman.

“It only hurts a little bit. Keep going.”

I thrust into his butt faster and faster, more and more, until I was there. “URRR! SO GOOD!”

Cindy opened the door and shrieked in shock. “EEEEH! WHAT ARE YOU DOING?”

I ran to the bedroom and shut the door. I dressed quickly and stared at the floor as I started to leave in shame.

Cindy said, “No, wait. Please? Let’s talk.”

I sat in their tattered recliner to discuss things with them.

Glenda said, “We still need the money, but I don’t think I can do anal again. That hurt a lot. What are we going to do?”

Cindy said, “I saw a news story that a girl sold her virginity online for a lot of money. How much will you pay for mine?”

At the same time, Glenda and I said, “No!”

Glenda said, “You should save it for a boy you really love.”

I told her, “You’re too young.”

“But you hurt dad’s butt. I heard sex only hurts girls the first time.”

Glenda said, “I’m not letting you do that! Not for money!”

She worriedly asked, “But then what are we going to do?”

I had an idea. “At Christmas time, she was in the men’s room and wanted to do what you usually do. Are both of you okay with her sucking me off?”

They looked at each other. Cindy was smiling and apparently eager. Glenda reluctantly said, “Okay.”

“So how about I pay for the car tomorrow, and visit your apartment instead of the gas station? Four blowjobs from Cindy over the next couple weeks, for the other four hundred you need?” They quickly agreed.

After four below-average blowjobs from the pretty brunette, we reached a deal that I could visit their apartment for a blowjob as many times as I wanted for three hundred a week. Glenda was much more skilled and felt better on me. On the other hand, Cindy was cute and I could watch her do it, instead of imagining somebody else. One of the father / daughter suck team made my cock happy nearly every night, sometimes twice.

Over time I learned Glen / Glenda’s story. He was brought up very religious and felt terrible guilt that he was attracted to men. He met with another boy in a restroom and discovered he loved performing oral on males. He fought his desires and married a young woman he kind of liked, and they had their daughter Cindy. When Cindy was only five, his wife caught him in bed with another man and left. She didn’t take Cindy, and rarely even asked about her during the divorce, but Glenda took good care of her.

Glenda thought that it was too shameful to be gay and have gay sex, and decided to get a sex change operation. He said he didn’t really care much whether he had a penis or vagina, he mostly wanted to suck dick and be accepted.

He saved for years, but couldn’t come close to enough money to have the surgery in the US. He went to a surgeon in South America to have it done cheaply, but the operation was badly botched. Glenda now had a mass of flesh the size of half a grapefruit protruding from his crotch area with a hole through it for his urethra. No penis, no testicles, no vagina, just a large, leathery lump. An American doctor told him that the scar tissue would make surgery to build a vagina or a new penis impossible. Glenda would never enjoy sex or feel an orgasm again. I felt very sad for him.

The incompetently done surgery also made it hard for him to stand or walk much. He could manage a couple of blocks if he took his time, but standing more than a ten minutes or walking quickly were too painful. Since he couldn’t be a construction foreman anymore, he had been getting by doing blowjobs at the glory hole and made much less than he used to.

He tried dressing like a woman but most people had very negative reactions, since his face and most of his body looked like a larger-than-average man. He switched back to dressing like a man and was happy doing several blowjobs a day for money, but craved acceptance.

He used the name “Glenda” for everything online, and in other situations where people wouldn’t see him. He wanted to be a woman because then it would be ok for him to love doing blowjobs. I thought it was quite sad and gave him a hug. He didn’t feel comfortable hugging because we were two men. It seemed wrong to him, even though he had sucked me off half an hour earlier. I at least partly understood, and kept calling him Glenda. In March when we were alone, Cindy offered to give me all the blowjobs I wanted for a day, so she could get a nice gift for her father’s birthday. She held my cock in her mouth nearly an hour, licking and sucking me off three times. It was Heavenly!

We had a small birthday party for Glenda and felt almost like a family. We sat on the sofa with Cindy between us, eating cake and ice cream. At 8pm there was a knock at the door. Cindy and Glenda were overjoyed when some movers took their old mattress and couch away, and replaced them with a new fold-out sofa and an actual queen-sized bed. Now they had comfortable places to sleep.

The size and shape made Cindy’s gift to her father obvious, but he was still very happy to get a flatscreen tv, to replace their small and very old tube-style one. I helped him hang it on the living room wall. We laid on the new bed together, and they took turns giving me blowjobs. I fell asleep holding Cindy to my chest, with her father’s arm wrapped over her holding my dick.

One night I got a surprise when I went to visit. I hadn’t seen them in three days. I was horny and eager for a blowjob. It was after 9, so Glenda was at the gas station. I parked a block away like usual, and saw Cindy standing near the door to their apartment building with a blonde girl. The two of them were smoking cigarettes! I stood and watched them suck on the cigarettes and blow out white smoke, nearly the color of jism. She wasn’t even 19 yet, much less 21. I knew it was bad for health reasons too, but seeing their faces as they smoked reminded me of blowjobs. It was wrong but arousing. I felt myself start to stiffen and willed my dick to deflate.

As I walked over, Cindy saw me and said, “Please don’t tell dad.” As I got closer she quietly said, “If you keep it a secret, Sherry will suck you too. Right Sherry?”

The cute blonde girl nodded. I made the right decision about Cindy for a change and grabbed the cigarettes away. “Smoking is terrible for you, and you’re too young. And I don’t know what you mean about sucking. Go home, Sherry. I’m going to wait with Cindy until her father gets home.”

Sherry walked off and Cindy objected, “But all kids try it. It’s not a big deal.”

“Smoking stinks, it’s expensive, and it’s terrible for your health.”