Saving Sucky Cindy Ch. 01

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Author's note: To fully understand the characters and situations, you should read the story 'Christmas Eve with Gloryhole Glenda' before this one.

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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.

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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 the two of them took turns sucking me off. I fell asleep holding Cindy to my chest, with her father's arm wrapped over her holding my dick.

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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."

She looked away in shame. "You're right."

I told her, "How about this? We'll talk with your dad and if he says it's ok, I'll let you smoke."

"But... but..."

"And you're lucky I'm not your dad, or you'd be getting a spanking right now."

We went inside and watched a basketball game until Glenda returned. I was happy Cindy was one of the uncommon girls who liked sports.

I reminded her, "Smoking makes it hard to breathe. You won't be able to play basketball much longer if you smoke."

She sighed, "I know."

I woke up with Cindy leaning on me asleep on the couch. Glenda was pushing on my shoulder. I woke Cindy, and we had the discussion about smoking. Glenda thought she should get a spanking too, but didn't want to do it. I couldn't bring myself to actually spank her either. I had an idea and whispered to Glenda. He nodded.

I said, "I've wondered what it would be like to give Cindy some oral too, instead of her sucking me all the time. Would that be okay with you, Glenda?"

"Uh... if she wants you to, I guess."

"So, would you like me to lick you between your legs, Cindy?"

"REALLY!"

I nodded and led her to the bedroom. She sat on the edge of the bed and I closed the door. "Cindy, I want to remind you, we're not in love. I'm not your boyfriend. I'm a friend, and we're doing this to feel good. That's all. Okay?"

"Okay. So how do we do this? What do I do?"

"You take your pants and underwear off and lay on the bed. I'll do the rest."

I had a good time licking and sucking her little pussy until she had her first three orgasms with another person.

"Did you like that, Cindy?"

"YES! OOOH! That was SO GREAT! THANK YOU!"

"I'm glad you liked it. I'll do that for you every weekend, as long as you don't smoke."

"THANK YOU! Thank you so much!"

Before long I gave in. Instead of just giving Cindy cunnilingus once each weekend, I did 69 with her four or five times a week. Each time, I came in her mouth and was happy to lick her to an orgasm or two. I still paid her father three hundred a week. It was a sixth of my salary, but I thought it was worth it. I also returned to the restroom glory hole for one of Glenda's wonderful blowjobs at least once a week, imagining he was a beautiful woman instead.

Cindy started becoming very affectionate and clingy. I reminded her several times, we weren't boyfriend / girlfriend. I didn't love her, I was just a friend doing it to feel good. She said she understood, but I could tell she wanted more.

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On one visit, Glenda was at the apartment alone. He said, "I have some medical problems, and need a few expensive tests done. I'm terribly ashamed to even think about this. If I didn't need the money so bad..."

I put a hand on his shoulder. "It's okay. Considering all I've done with you and your daughter, I think you can tell me anything, right?"

He smiled sadly a moment. "You're a good friend. A long time ago, we talked a little about Cindy selling her virginity. I don't really like the idea, and I wouldn't trust anybody else with her. I didn't say anything about being sick or needing the money, but Cindy told me she wants to make love to you." He let out a big sigh in resignation.

"I know it's a lot, but I need seven thousand. Is there any way you can..."

I took out my checkbook and started writing.

I said, "I know you're worried about her safety. I'll do it with her while you're in the other room, so you can know she's safe. You know that losing their virginity always hurts girls the first time they make love? I'll try to make it as easy as I can for her. She's pretty and I want to have sex with her, but I want to know my friends are both okay too."

I patted his shoulder and Glenda hugged me as he cried. "Thank you."

After a long hug he said, "Screw her, but don't make love to her. I don't want her getting the wrong idea. Don't let her think you love her unless you really do. And..." He hesitated a long time.

"And I don't have any family but Cindy, and not a lot of friends. Just in case, could you sign something?"

He brought out a will. "If anything happens to me, I want to know Cindy will be taken care of. Would you please?"

"I... uh... I don't know anything about raising kids. I don't think I can take care of a kid!"

He chuckled to himself. "It's not like she needs bottles and diapers, she graduated a few months ago! If you can fuck her can you at least let her stay with you, and give her what she needs?"

I chuckled too. "Yeah. I guess I can do that."

He had a serious look in his eyes as he said, "But don't tell her you love her unless you really mean it. Don't break my baby's heart!"

I had a lump in my throat. "No. Never."

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The virginity removal was almost clinical. The three of us sat in their living room talking.

I handed Cindy two pills. "This one will reduce the pain a lot and the other will slow the bleeding, so that won't be bad either."

She swallowed them and washed them down with some water.

I said, "Both of you know the first time I enter her, it'll hurt. She might yell from the pain, but don't worry. It only hurts a lot the first minute or so. Everything will be okay."

Glenda held Cindy's hand. "I'm so scared for her. Would it be too weird if I watch?"

Cindy said, "Really weird! But... if James is okay with it, I guess?"

The two of them looked at me. "Uh... I don't know if I can do it with your dad watching. Uh..."

Glenda suggested, "How about if I suck you right before? Then you can just do what you need to, without taking a long time to get ready?"

"Uh... I guess."

Cindy stood up as she asked, "How long until the pill starts to... WOOHOO! I'm swimming!" She flailed her arms around and I caught her as she started to fall over.

I laughed. "I'm pretty sure it's working." I carried her to the bed and helped her undress, then took my pants off.

Cindy asked, "How can I help?" She tried to get up and failed.

Glenda told her, "Just lay still, sweetie. Everything's fine."

For the first time, I watched Glenda lick and suck my penis. I wasn't attracted to his face or body at all, but I could tell he loved me, and loved his daughter dearly.

The thought that he loved me and trusted me to take his daughter's virginity touched my heart. Imagining how great it would be to fuck a tight, pretty virgin made me hard enough to drive nails with my penis. I pulled out of his mouth and he quickly rolled a condom on me. As I crawled on top of Cindy, he held one of her legs to make it easy for me to get myself lined up.

I kissed her lips and Cindy groggily said, "This is nice, but I thought sex would feel better."

I looked into her dilated and glassy eyes. "I didn't start yet. I'm sorry, but this will hurt for a little while, then it should feel good."

Glenda smeared some extra lube on the condom and stroked me a few times, then I thrust into Cindy.

I expected a scream, but instead she just said, "Uhhh!"

I felt her hot, wet snatch squeezing my cock tightly. Even with the condom, it was excellent!

I held still inside her and nervously asked, "Are you okay, Cindy?"

She made her father and I laugh with, "I thought it was supposed to hurt. That felt like a big, backwards fart."

Glenda and I laughed, and Cindy wondered aloud, "What's so funny?"

Glenda said, "We'll tell you later. I'm so glad you're okay! I was really worried!"

I said, "Thanks for the help, but I think we're all right now. Would you mind leaving?"

He chuckled, "Sure. Sure."

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We had agreed that after Cindy's first time, I wouldn't see her again for two weeks to avoid her getting overly attached to me, and I would only have sex with her again if Glenda agreed.

For the two weeks, I returned to getting anonymous blowjobs at the gloryhole, paying Glenda each time, until I went back to mostly 69 with Cindy.

She seemed even more clingy than before, and several times she started to say, "I love you" and stopped herself. I didn't want her getting too attached, so I went back to the glory hole and only visited their place when Glenda was there. One night Cindy was standing in the parking lot by the gas station men's room, a few steps from where her father had sucked me off hundreds of times.

She started to cry as she asked, "What did I do wrong? Why are you mad at me?"

"I'm not mad. I still like you, but I don't want you getting hurt. We make each other feel good and I help your family out, but that's all. I want you to be happy, but I can't be more than your friend."

She nearly screamed, loudly saying, "FINE! Then have fun FUCKING MY DAD'S FACE! Bye!" She kept crying and walked away.

I wasn't horny anymore. I felt guilty and decided to go home. I saw Cindy light a cigarette as I drove off.

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