by Wyn Mallory
“Don’t stand up until you’re ready,” I tell her. “I don’t want you to go until you feel strong enough.”
“I feel okay,” she says. “But I want to make you feel good too. It’s not fair if it’s just me.”
She’s a sweetheart, but I’m not going to let myself get carried away any more.
Chapter 5
Lindsay
I can’t believe that just happened. Not one, but four orgasms. And I wanted a fifth. I wanted him to give it to me with his penis and to take his pleasure at the same time. To come inside my pussy and experience just a fraction of what I’ve been experiencing. Sitting down, I reach out for him and feel his tight balls and cock pressing against the fabric of his trousers. He was groaning and desperate for it a moment ago. I know he needs release, and I want to give it to him. If he won’t take my pussy, maybe I can suck him off instead. Thinking about taking him into my mouth and sucking on a dick for the first time gets me feeling hot again. I start to unzip his trousers, but he backs away.
“It’s not that I don’t want it, because I do. Badly,” he says. “I want to come in your hands, in your mouth, and in your pussy. But I’m not taking advantage of you.”
“It wouldn’t be taking advantage because I want it too,” I protest. Hell, I’m starting to need it. I’ve never felt anything like this and can’t stop longing for more.
“Not now,” he insists. “Maybe some time, in different circumstances, but right now I have responsibilities toward you, and I’ve already broken all the rules. I never break rules.”
“Me neither,” I say. “I shouldn’t have tempted you.”
He laughs. “You couldn’t have prevented that. It was always going to happen. I was tempted the first second I saw you.”
“So was I,” I blurt out in more honesty than I intended. I can’t seem to stop myself from telling him things.
“You’ve really never been with a guy? Have you had a boyfriend?”
“A few, but nothing ever happened with any of them. I didn’t want to rush into anything. My last boyfriend, the one I had when I was arrested, tried to touch me a few times, but it didn’t feel right. He wasn’t the guy for me, and I was thinking that I really should break up with him and let him go out with somebody else.”
“He didn’t touch you? Not even stroking your breasts?”
“No.”
“But you just let me touch and see everything?”
“It just felt right,” I say. “I wanted you to touch and look at me.
“And put my hands and mouth on you?”
I remember begging him to lick me and feel myself blushing again. “I liked everything you did, but it’s kind of embarrassing that I asked for it.”
“You shouldn’t be embarrassed about pleasure,” he says. “I’d like to help you get over that and teach you to tell me exactly what you want and how you like to be touched. This is crazy though. I shouldn’t have started this, or taken it so far, but I wanted you so badly. I still do. I don’t just mean sex. I want to be with you, but there’s this little situation where I’m your probation officer.”
I’m thrilled to hear him say he wants me. “I want you too. I know it’s wrong, but I can’t stop feeling it. Do you have to be my probation officer?”
“Maybe not, but you’ll still be coming to this office. What I did was totally out of line, and I should never have done it here. I liked doing those things to you as well, but I’m feeling guilty about how it happened. I want you to know that I’ve never done anything like this before, and believe me, I’ve had plenty of opportunities. I could probably fuck half the women who come though my office, but I’ve never even been tempted. This was different. I felt something special about you straight away.”
“I felt something for you as well,” I admit.
“This isn’t over by any means,” he says. “Somewhere down the road, I’d like to be with you, but it can’t be now.”
My heart is soaring. “I can wait. It’s worth waiting for.”
“I just wish you didn’t have to go to a shelter. I want to take you home with me, but you’d end up in my bed, and things would be more complicated than they already are.”
“I wouldn’t mind being in your bed. In fact, I think I’d like it, but I don’t want to get you in trouble. I’m okay with going to a shelter. And tomorrow I’ll start looking for a job, so that I can afford to find a place to live. Somewhere really cheap, I guess. There’s a lot I’ll have to learn in the next while, but I will be able to take care of myself.”
“Starting right now, if you feel up to standing. There’s some stuff I have to do, so I need to get going much as I hate to leave you. Just promise me you’ll take care.”
“I will. I’ll stay in groups and keep safe like you told me.”
“Then I’ll see you tomorrow at 5, at which time we’re both going to behave ourselves, right?”
“Sure,” I say. “I promise to be good. For now.”
I’m pretty sure I hear him muffle another groan.
Chapter 6
Riley
After leaving the office, I make a couple of calls. They’re both surprise visits, to check on a couple of guys I’ve been having some doubts about. We do that a lot, and what we find out is often a big disappointment. Too many people just can’t get away from a criminal lifestyle. I’m used to it, and what I do helps to keep innocent people safe, but I kind of hate being the guy who sends someone back to prison. Sure enough, the first call reveals a situation I have to deal with.
On the second call, however, the surprise is all mine. He’s playing a guitar, drinking pop, and hanging with some friends, who don’t seem too bad. A couple of them are drinking beer, but they’re a sober crowd having a good time making music. I don’t see any signs of drugs or other trouble. When he tells me that he’s celebrating getting a job and he starts tomorrow, my face breaks into a smile. I’ll be making sure it’s legit, and watching closely for a while, but I think I might be notching this one up as a success. I shake his hand and wish him luck with the new job.
After that, I head to the hospital to visit Ed Willis. His wife is there, looking very tired and worried. Kind of pale too, which reminds me of Lindsay when she nearly fainted. Promising to keep the conversation light, I make her go and find something to eat while I sit with him. Of course, the first thing he does is ask how everything is in the office.
“Hey, no talking about work,” I chide him with a smile.
“As if I ever think about anything else. I guess that’s what got me in this hospital bed, but I’m not regretting it. We make a difference. But from now on, I’ll be making my contribution to the world by growing flowers for my neighbours to enjoy. They say I can garden as long as I get someone to do the heavy jobs. Thank goodness for that.”
Ed has always loved his garden. It’s probably helped to keep him on steady ground all these years. “I’ll come around and do some digging for you,” I promise.
“I just want to say one thing about this morning. It’s not really talking about work, but there’s somebody I’d like you to thank for me. She kept asking if I was okay and insisted on getting me a glass of water. I took the glass back after she left, and that’s why I collapsed up front instead of in my office. I might otherwise have gone without help for too long. They said it could’ve been worse if I hadn’t gotten attention so quickly. I can’t remember her name, but she was pretty.
“Lindsay,” I say at once.
“That’s it. Pretty name too. It was nice of her to care.”
“She is nice. To tell the truth, I’m worried about her. She doesn’t have anywhere to live. I gave her the shelter list, but I think she’s going to find things rough.”
Ed looked surprised. “She told me this morning that she was going home.”
“I guess that’s what she thought at the time, but her parents kicked her out.”
“I hate it when they do that. It’s so much easier for these kids to rehabilitate if they are
not lost and alone. I wasn’t too worried about her because it seemed like she was going to be in a good place, but now it’s going to be a lot harder for her. Keep a good eye on her for me. I liked her, even aside from being grateful that she helped me.”
I’ll be keeping an eye on her alright, but I can’t tell him yet what she means to me. “I intend to,” I promise him. “I don’t think she’ll make it on her own in a tough world. She doesn’t act like prison changed her much.”
“I doubt it did. As I understand, she spent most of her time reading in the prison library. Luckily for her, there was one.”
“I can imagine her doing that. She looks like the studious type. It’s hard to believe that she would shoplift. I heard her say she rushed to get to the office before we closed so that she could tell us promptly about the change in her circumstances. She’s the type who follows rules. She even told me so.”
I just realized that has been playing at the back of my mind since she said it. I start thinking that she really is clean and never stole anything.
“Probably a stupid dare,” Ed suggests. “We’ve known that to happen too often. Unfortunately, the consequences can be life-changing. In this case, she lost her scholarship. That’s something she might never recover from.”
“She didn’t mention that. We didn’t really have time to talk much, but I scheduled her in for tomorrow, and I want to see what I can do to help her get on her feet. I don’t consider her a risk to reoffend, so I’ll probably have to look up some training program or something for her on my own time. I’ll be spending most of my day focusing on some more serious cases, but I promise hers won’t just go on the backburner.”
Ed looked contrite. “I guess you’re all working extra hard because of me.”
“Hey, don’t go there. You know how we all thrive on overwork,” I joke. “Seriously, we’re doing fine. We’ll be putting in a little extra time for a few days, but it’s not like that’s anything new.”
“I bet Jack was still there when you left.”
I laugh. “Jack’s always there late. He’s even more dedicated than you were.”
“Were,” Ed repeats. “It just sounds weird knowing that I’m not going to be working anymore.”
“You’ll be living the dream,” I tell him
“I hope it doesn’t get boring. I’m used to being busy. Hell, I actually like my job. Liked. I mean. And I’m going to miss you guys.”
“What’s to miss. You’ll be by to have coffee with us all the time.”
He grins. “Herbal tea for me, according to my doctor.”
“We’ll get some,” I promise him, relieved to hear him accepting the state of affairs. No use fighting the doctor’s orders.
On the drive home, I’m thinking about Lindsay and wondering what kind of job she might be able to get. Minimum wage probably, and she’ll hardly be able to make enough money to get by, let alone save up. Her future would be looking bad right now, that I’m going to be taking care of her. Still, I get the feeling she’ll want to do something useful, so I still plan to do some research and hope it will turn up something. It’s been a long day, and I’m exhausted, but I spend a few minutes looking up some stuff on my laptop while I grab something to eat.
Lindsay is still on my mind as I start taking my clothes off to take a shower, but now I’m thinking about her soft curves. While unbuttoning my shirt, I remember those rosy, hard nipples and blood surges into my cock. It springs to attention as I take off my trousers, begging me to relieve the throbbing pressure. I grasp my cock with my hand and start stroking up and down. It feels so good. I think of Lindsay’s wet pussy, and it pushes me to the edge. I’m just about to cum when another image darts into my mind. Lindsay lying in a shelter bed, scared and lonely.
My hand lets go of my cock. It’s agony to stop at the last second, but I can’t get off to thoughts of her while she’s suffering. My cock’s enormous and pulsing, and I’m desperate for relief, but I’m going to suffer instead of taking my pleasure with that image on my mind.
I turn on the shower, cold water only. Usually I like it steamy hot. It’s a great way to end the day and get relaxed for bed, but I won’t be relaxing tonight, and I need the icy water to chill my need and shrink my dick. When I get out of the shower, I’m shivering and the problem is under control for the moment, but it’s already stirring again as I get into bed. I can’t help thinking of Lindsay. Her trusting eyes, her gorgeous body and her smooth, slick pussy.
I’m groaning with desire and agony at the same time.
It’s going to be a long, hard night. Really hard, but I’m determined not to give in.
Chapter 7
Lindsay
I didn’t get into a shelter. The first one I went to couldn’t take me because I hadn’t spent the night on the street yet, so I wasn’t technically homeless by their policy. At another place, I stood in a line for a long time, but the person in front of me was the last one who got in for the night. Before she went inside, she looked at me and said, “Sorry.” I was already learning that this was a rough world, like Mr. Brent warned me, but there were moments of kindness as well.
At the next place, a man told me that there might be one bed left, but then he told me what I had to do to get that bed. I refused and ran out of there fast. After that, it was too late to get in anywhere, but a woman gave me a blanket. Another act of kindness, which helped to make up for the pervert. I wondered how many people had given him what he wanted so they could have a place to sleep, and I felt sorry for them. And angry. It was despicable that he got his rocks off by preying on vulnerable people.
I went to a park, and found an out of the way place where I hoped nobody would see me. I was feeling nervous about some of the guys on the streets.
So now I’m lying on the ground, wrapped in my blanket and looking at the stars in the sky. It’s like camping. Without a tent. Or friends.
But I still have people who care about me. I think of everybody who has been kind to me today. Especially Mr. Brent. His jacket is helping to keep me warm, and it reminds me that I’m not alone in the world. Things will be tough for a while, but I’m going to get through this. I’ll work two jobs if necessary, and I’ll make new friends. And there’s that wonderful prospect of being with him one day. It’s weird that I don’t even know his first name, but maybe better that way. He’ll tell me some time, when it’s okay for us to be together.
I pull his jacket close to my face and smell a lingering hint of his scent. It reminds me of how I felt when he touched me today, and my body fills with heat. Guess I don’t have to worry about being cold tonight.
I wish he had let me touch his cock. I wanted to make him feel good. And he was so hard. I bet it took a long time for that swelling to go down. If it did. Maybe he’s still hard. Maybe he’s lying in bed right now, stroking himself and finally getting the release he needs. I hope he is. I close my eyes and imagine his hands running down that muscular abdomen and grasping his cock.
In my mind, I see him jerking with the pleasure brought on by his own touch. A few gentle strokes to start, but then he speeds up, and soon he’s pumping vigorously. Thinking of me, I hope. Picturing his chest pressed against my breasts, and his cock inside my hot, wet pussy, gliding easily in and out. Imagining the walls of my cunt stroking his enormous manhood, flexing with their own pleasure and pulsing around his cock. Coaxing him to a blinding orgasm. His hips rise off the bed and start bucking into the air. He pounds his dick into his hand, and hot cum bursts out, splashing over his firm abs and chest. He milks every drop before collapsing back and savoring the satisfaction.
The heat and juices are welling up inside me again, and my pussy is longing to be stroked. I guess four orgasms weren’t enough. Now I need another. I wish he was here to take care of it, but this is a job I’ll have to do for myself. I undo my jeans and push them down a few inches. As I do so, the touch of my hands against my bare skin sets me aflame. I remember his hands on my body, and my abdomen aches with wantin
g him to touch me.
Both hands steal inside my panties and rub all around my pussy, squeezing and massaging the outside, prolonging the moment of pleasure and heightening my need. I imagine that it’s his hands touching me, still covered with warm cum that he’s rubbing into my pussy. When I slip a finger into my hot slit, moisture gushes out to meet it.
My clit is huge and pulsing. I’ve never felt it so large before. Still recalling his touch, I need three fingers to satisfy it. They glide easily over the hot flesh, and I rub every part of it, sliding my fingers into the slick folds like he did, thrusting them in and out of my pussy, and stroking circles around my clit. I’m burning with need but it’s still not enough. I rub faster and faster over the swollen nub, bringing myself vigorously to a climax. It’s not as good as anything I felt earlier today, but better than any orgasm I’ve ever given myself. Usually it’s one or two quick bursts and all over, but this time the pleasure lasts longer while I stifle moans of delight.
All the while, my probation officer is in my mind. He’s the one giving me the fifth best orgasm I’ve ever had. When I finally pull my hand away, I start to feel the desire building up again. This was only temporary relief. What I really need is his cock inside me, and my pussy won’t be fully satisfied until I get it.
At least I won’t be cold tonight. Thinking of him will keep me toasty warm all over. I’m drifting off to sleep on a cloud of hazy pleasure.
I don’t know if it’s the sun shining in my eyes or the cold, hard ground at my back that wakes me up. I look up at the sky and experience a brief moment of confusion before remembering that I am homeless. No comfortable bedroom that I was looking forward to, but also no bars, no locks, no guards. I’m free. Surrounded by grass and trees.
