“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.
–
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.”
–
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.”
–
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. Cindy lit a cigarette as I drove off.
–
One night I returned after being out of town two weeks on business trips. I stopped at their apartment, but the door was locked. I knocked but nobody answered. I thought that was odd, since Glenda’s car was in the driveway.
I went to the gas station and saw a guy walk out of the men’s room with a big smile on his face. I thought, “Glenda’s here. Good, getting rid of some sperm will feel great.” When I walked in the men’s room, I smelled cigarette smoke. I went in the usual stall, and some small red fingernails reached through the hole for my money, instead of Glenda’s usual large purple ones.
I asked, “What’s wrong, Cindy? Is your dad sick again?”
I could hear the pain and anger in her voice. “Dad’s in the hospital and I need money. Do you want a blowjob?”
Her fingers sticking through the hole motioned for me to pay.
“I… I’m so sorry. I’ll help again if I can.”
“If you’re not gonna pay, get in here. I need to make as much as I can to help dad. You’ll scare the other guys away.” I heard the other stall door unlatch.
I walked into the other stall slowly. She was sitting on the toilet, and moved so I could sit there, while she sat on a towel by the glory hole.
I said, “I’m sorry I hurt your feelings. I want what’s best for you. You shouldn’t be falling in love until you’re older. I think …”
We heard the restroom door open, and she held a finger to my lips. “Shhh…”
We heard a few footsteps, but they paused before whoever it was entered the other stall. She said, “It’s ok, I’m teaching a friend tonight. Come on in.”
A deep man’s voice asked, “You’re not cops, right? If you’re cops, you have to tell me.” Not true, but apparently he didn’t know that.
She reassured him, “We’re not cops. And I’m not saying anything about sex or money if you’re not.”
“Okay then.”
She held her fingers through the hole and took his money. A moment later a very large black penis stuck through the hole. She squatted down to lick and suck it, and I watched from two feet away. I was surprised she could get several inches in her mouth. The head was nearly the size of a baseball!
Watching her lick and suck it quickly got me hard. Nobody was touching my crotch, but by the time she squirted the guy’s cum onto the floor between her knees, I was halfway to climax too.
He complimented her, “Mmmm, babygirl! That’s some fine suckin’! You want to go again?”
I saw a folded fifty sticking through the hole. Cindy looked at me as I shook my head.
She took the money, saying, “Sure”. She used a baby wipe from her purse to clean him, before she started sucking again. She rested a hand on my crotch as she sucked, but didn’t squeeze or rub me.
I watched her take her mouth off him just in time, and she caught his second load with another baby wipe. My cock was as hard as the wall, and I wanted to cum desperately. I pulled a fifty from my wallet. As the other guy left and the door closed, I held out the cash and begged, “Me too! Please!”
She asked, “Do you love me? Am I your girlfriend?”
“No, but I have money…”
“I don’t want your money. I’ll suck you when you love me. I’ll even fuck you too. So, do you really love me?”
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