One day I was surfing around the dating site Plenty Of Fish (POF) when I came upon the profile of a skinny woman in her late 40’s. Under the intent section it listed that she “isn’t seeking a relationship or any kind of commitment” which more often than not means she’s looking for hook ups. Based on her profile it looked like she was likely uneducated and lower class. I shot her a message asking how things were going in her world.

I pretty quickly got a reply. It consisted of a ramble about how none of the guys on the site would help her. Her life was falling apart, was badly in need of some help and the guys wanted sex in return for helping her. “so you need help, for what” I asked. She tells me she and her 14 year old daughter got kicked out of the weekly motel they were staying in because she ran out of money. Worse still, the motel kept all of their stuff and it would cost $150 to get it back. They only had the clothes on their backs. She had no way of getting to work, her daughter was staying with a friend for now and she was on the street. She asked if I could help? I got her number and we started to text instead of messaging on POF.

She was about 30 minutes away from me on the other side of town. She hadn’t eaten in 2 days, was on the street and her daughter could only stay at her friends for another night or two and would then be on the street with her. I said I couldn’t do much and only had about 2 hours before I had to get to work but I could meet her and give her a few bucks so she could eat. She was thrilled and told me to meet her at a McDonalds.

About 45 minutes later I walk into McDonalds and see her sitting in a quiet corner. She was happy and relieved I actually showed up. She gets up to greet me and I discreetly check her out. She’s plain but certainly not ugly. Dark hair, what look to be C-cup breasts, a slender body with skinny legs. I sat down across from her and she begins to tell me how desperate things are looking for her and her daughter, but for now would simply be thankful if she had enough to get something to eat. I was originally going to give her $20 but was feeling generous and gave her $40. She was thrilled. I told her I had to get to work but perhaps I could help her more in a day or two if she didn’t have any luck finding help. She hugged me and I left. The entire time simply being a benevolent guy willing to help.

The next day she sends me a text. She’s still on the street, hasn’t found anyone to help and could I please do something to help her. I asked how much she needed and she said at least $200 to get the room back for a week because tonight would be the last night her daughter could stay with at her friend and they would both be on the street the next day. And to make things worse for her the next day was the girls birthday. She was hoping for a little extra from me to get the girl a present. I told her I could possibly do that, but, I would want her to do something for me in return. She said she understood and expected that and asked what I wanted.

I told her I wanted a full 2 hours of her sucking me, fucking her and anal and cuming as many times as I could in the 2 hours. Without any reluctance she agreed. I told her I’d contact her in the morning and arrange to pick her up.
The next morning she hits me up around 8:30 asking if I was still going to meet her. I assured her I would pick her up around 11. She mentions that the $200 will get her the room back for week but she still won’t be able to get her stuff back or be able to eat. “So now you’d like almost $500 between everything?” “If you could, we need our clothes and to be able to eat”. I told her I’d see what we can work out.

“Also, my daughter is with me, she has no place to go can I bring her with me?” I ask “And what will she do while we are alone?” “She’ll behave and be fine on the couch watching TV.” I’m not so convinced saying “Are you sure? For a full 2 hours?” She tries to sound convincing saying “she’ll do what I say, especially if it means not being on the street”.

I pull up to pick her up and see this adorable young girl with her. Sweet face, glasses, skinny and her short shorts and tiny tee show that she is just beginning to bud. They hop in and I wish the girl a happy birthday. She thanks me for being nice and helping them. We get to my place and I ask if they’d like the chance to shower. Mom says yes since she’s been on the street and they go to the bathroom together. The idea of them naked and showering together gets my mind going.

When they’re finished we hang out on the couch for a bit and I whisper to her Mom if she’s ready. She tells me to hang on a minute. I got to the kitchen and here them talking. Mom comes over and asks if I’m going to be able to give her the full $500 she needs. “It depends, can you still give me what I want, and maybe more since it’s more than twice what we agreed on?” She hesitates and says the girl isn’t comfortable being left alone for 2 hours. “Well, that means I don’t even get what we agreed on for $200 and you want $500?” She said she would, but it’s her birthday and she wants to be nice to her. “Please, can you help me anyway? I’m desperate, you’re my last chance to keep us from being on the street!”

“Why would I do that? Almost seems you are trying to play me. Bait and switch and not give me much. You are the one that needs this, not me!” She starts to tear up and says “I’m begging you, I can’t let us end up on the street!” I tell her “sometimes desperate times call for desperate measures. I guess it’s time for you to decide if you are willing to do what it takes to stay off the street. You said she’d do what you say, that you would give me two hours, but now you are begging but not willing to do any of that. Seems you either must not be that desperate or not be afraid of you and your girl living and sleeping on the street with only skimpy clothes on!” “Noooooo PLEASE! I can’t let that happen!” “Well, since you backed out of what you said you would do here is your choice……… I either take you back to your side of town and drop you off to survive on the street, or, you can’t get the $500 plus $250 more which will totally fix your situation. You get the room, your shit back, money to eat for a while and a present for her, IF you do what I want which includes proving to me that she will do what you say.” With tears in her eye she asks “what do you want?”

“I want you to give me everything we agreed upon, and, tell her that she does not have to be alone…… she will join us!” With wide eyes and tears in her eyes she asks “what do you mean she joins us?” I look her firmly in the eye and say “It means I get to do what we agreed on with both of you!” She freaks and says “I can’t make her do that! PLEASE!” I tell her “no problem, that’s your choice. Time to get in the car and I’ll take you to the streets.” “Noooooo PLEASE!!!”

“YES! Either we go into the bedroom or we get in the car, NOW!” She starts to tremble and cry. “I mean it, decision time. I’m not wasting anymore time!” With tears in her eyes she goes to the other room. I hear her say something to the girl. The girl shouts “NO!” and starts to cry. I hear them talking back and forth, both crying and after a few minutes Mom comes back over to me and says “OK we will do what you want” and breaks down crying. I remind her “For the full 2 hours” and she nods in agreement.

I go to my room, quickly pop a 100mg little purple pill to ensure quick recovery and consistent hard ons for the full 2 hours and tell them to follow. Slowly and hesitantly they do. I walk to the girl and gently stroke her hair. Trembling and with tears in her eyes she flinches as I do so. I lean in and kiss her cheek and whisper to her “it’s ok, be a big girl. You’re gonna help save you and your Mom from being on the street. You will become a woman today.” I move and stand behind the girl and with us both facing Mom tell Mom to take off her clothes. They both start to cry and Mom slowly removes her top and bra. She’s thin and pretty shapely but once released her tits hang down and sag show how they’ve lost their firmness. As she starts unbuttoning her shorts I reach around placing my arms around her belly and pull the girl tight up against me. I feel her trembling as I start to caress her belly. My pants start to bulge and she can feel my hard cock pressing against her. She just sort of freezes.

Mom is out of her shorts and slowly takes off her panties. As she stands there she watches as I reach up under the girls shirt and slowly rub on her tiny breast. She has firm little mound and tiny nipples. She whimpers as my finger gently rubs her nipple in a circular motion. Whispering in her ear I ask “have you ever let a boy touch you like this?”. “No, I’ve never done anything with a boy before.” By this time Mom is naked in front of us. She’s no hard body but she’s slender with a pretty flat stomach with a closely trimmed triangle of dark pussy hair.

I tell Mom to come stand next to the girl. I step behind them and reach around and start rubbing on Moms tits. I move my hands and gently rub her bare ass. I whisper in her ear that I am going to enjoy this and hope she does too. She simply lowers her head in silence and whimpers. I move a hand to the girl’s ass and start exploring it over her shorts. She’s trembling and this makes me hard as a rock. She squirms when I reach between her little ass cheeks and move my hand to her pussy. I ask her “do you know what I’m going to do with this?” She can barely get out a reply of “I think so” as she totally busts out crying. “Don’t worry” I console her, not right now, we have other games to play.

I move in front of them and tell Mom to get on her knees. The girl turns her head away as I slip of my shorts. I place my hand on her cheek and tell her to look down at my cock. “Have you ever seen one of these?” She slowly responds “Noooooo” as her eyes get wide. I’m only average sized, about 6 ½” but to this little thing I probably looked huge. “Now watch what Momma can do to it” as I look down at Mom and give her a wink as her que. The girl is mesmerized as Mom opens her mouth and takes the tip of my cock into her mouth. “Now show your baby how it’s done.” She lets out a short cry and begins to slowly take my cock deeper into her mouth, slowly comes back up and then begins a slow rhythmical blow job.

I whisper to the girl “now you keep watching how she is making me feel soooooo good.” With Mom sucking my cock I lean over and begin to kiss the girl on the neck. Her skin is so soft and she smells so sweet. I run my hand under her shirt and gently rub her titties. After a bit I grab the bottom of her shirt and lift it up and off exposing her sweet little mounds. She tries to cross her arms to cover them and I pull her arms to the side, look her in the eye and firmly tell her to behave. I bend in and start to suck on her tiny pink nipple. She jumps a bit and I reach one arm behind her and pull her into me firmly embedding her breast in my mouth. She begins to relax and I move to the other breast, gently lick the nipple, sucking it into my mouth and circling my tongue around while enjoying Moms mouth riding up and down on my cock.

I lean back and tell her to watch some more. I reach down placing one hand on the back of Moms head and begin to slowly thrust into her mouth. I say “it’s time for the good stuff girls” as I hold her head in place and slowly push deeper into her mouth. She tries to push back but I apply more force and push my cock deeper until it touches the entrance to her throat. She gags a little and I back off, remove my hand, and let her resume her dutiful rhythm. I then reach over and begin to rub the front of the girls shorts. She trembles again as I place my hand fully on her crotch.

I can feel the warmth of her virgin pussy through her shorts almost causing me to blow in her Moms mouth. Not wanting that yet I pull out of her mouth and tell her to lick my balls. I reach for the button on her shorts and the girl again begins to cry. I slowly undo her shorts and push them down until they slid down her legs to the floor. I tell her to “get them all the way off”, she steps out of them and I kick them away. I now start to rub her pussy over her soft cotton girly panties. She trembles more than she has yet before as I slip my hand down the front of her panties. My fingers quickly find her peach fuzz covered labia. I gently rub her virgin pussy before beginning to slide my finger up and down her slit opening her up lips allowing my finger to eventually find her tiny little clit. As I begin to rub it she shudders. I lean in a whisper in her ear “that is what it feels like to be a woman.” I continue to rub her clit and begin a gentle circular motion. When I slid my finger down her slit I discover the slightest bit of wetness. I guess no female can avoid the natural reaction of being stimulated. I smile, grab the elastic band of her panties and pull them down. When they fall she steps out of them without being told.

I put my cock back in Moms mouth and she resumes her slow rhythm. I bend in and again start sucking those precious little titties and rubbing that lovely virgin clit. I slide my finger up and down her slit and as she and she is getting wetter. Placing my finger at the entrance to her little hole I begin to push it in a little. She shudders, trembles and begins to cry one again. She is soooooo tight but I push in a little further feeling her warm wetness tightly gripping my finger. I begin to ease it in and out and as I get deeper I realize I do not feel her hymen. Slowly probing my middle finger all the way in it is apparent that while she is clearly an untouched virgin, her cherry has been popped by some other experience. I understand this can happen horseback riding and other ways and decide it’s a very good thing. There will be no blood and pain from popping her cherry but I still get to enjoy taking her tight, tiny virginity.

I remove my finger and raise it to my nose. She smells wonderful. I push Moms face off my cock and stick my finger to her lips. “Suck this!” As she does I ask “how do you like the taste of virgin pussy?” She looks at me with tears in her eyes. I tell the girl “it’s your turn, get on your knees next to your mother.” She hesitates. I put my hand on her shoulder and push her down. She relents and now I have both of them on their knees in from of me. I put my cock to her lips and tell her to open her mouth. She tears up and trembles again as she opens her mouth. I place the head of my cock in her mouth and tell her to lick on it. She moves her tongue over the head as I push just a bit more into her mouth. “Now suck on it like your mother showed you.” She looks up with a pleading in her eyes. “Tell her to do it Mom!” Mom tells her it will be ok and gently pushes on the back of her head. She follows her Mom’s instruction and takes a little more of my cock into her mouth. I tell her “up and down baby” and she begins to give her first blow job slowly taking more of me into her mouth until she is handling about half of my length in her mouth. I place my hand behind her head and gently push her head further onto my cock allowing her to get into a rhythm.

I tell her to look up at me, hold her head still and start to fuck her pretty little face. I’m on fire as I look into her eyes and begin to thrust faster and deeper into her mouth. Then I slow down and take slow methodical thrusts, each one testing how much deeper she can take it. I hit her throat causing her to start to gag and I back off. Then, I take one last thrust shoving my cock deep into her mouth and holding her head there for a moment while she gagged before backing off and removing my cock from her mouth. She’s drooling and crying as I tell her “I promise not to do that again.”

I tell Mom to lay on her back on the bed and I have the girl sit next to her telling her to scoot up and sit about even with her Moms breast facing her feet. I spread Moms legs and position myself between them with my cock hard and pointing toward her pussy. I instruct the girl “now lean forward and watch as I put my cock in your Moms pussy.” Her eyes go wide as I begin to rub my cock up and down between her Moms pussy lips. “Here we go” I announce as I push my head in. I pull out and push back in a bit deeper allowing her pussy to open and accept my cock. Then I begin to fuck her going deeper and deeper until I’m balls deep with every thrust. Her pussy is warm and wet and quite tight and I pick up my pace. I push her knees back and begin to fuck the hell out of her. By now she’s wet as hell and moaning in pleasure. The girl’s eyes are still locked on watching my cock disappear with each thrust. “See how much your Mom likes getting fucked?” I ask her. She shakes her head yes keeping her eyes glued on the action.

Mom can’t help herself as she moans louder and louder and starts to fuck back like crazy. Before I know it she starts to scream “Oh God” and I feel her pussy tighten around my cock as she let’s go with a massive orgasm. I tell the girl to look at her Moms face. “You see how much she enjoyed that? That’s called an orgasm.” Mom turns away embarrassed. Then I say “But I haven’t had my orgasm yet. And I plan on having more than one today!”

I decide the little one needs to get her first taste of cum. I push her down onto her back, straddle her face and place my cock to her lips. I tell her to lick it. As she does I tell her “That’s your Moms pussy you’re tasting. I hope you like it” and then put my cock into her mouth and begin to fuck her face. I thrust deep and fast but back off from the temptation of ramming my cock totally down her throat. It doesn’t take long before I feel the pressure starting to build in my balls. I tell her “I am going to cum in your mouth and you are going to swallow every drop!” Her eyes open and she gives me a tearful pleading look. Her hopes are dashed when I respond with a deep thrust. I continue to fuck the hell out of her mouth until I knew I couldn’t last much longer. I tell her “Here it comes baby!” and I push into her mouth, hold her head in place and explode like I haven’t in a long time. Waves of intensity pulse though my entire body each culminating in a huge burst of man fluid pouring into her mouth. She freaks out but with my grip in place has no option but to swallow it all. I hold my cock in her mouth as the spasms slowly reduce in intensity until I am fully spent. I pull out and she’s crying and gasping for breath, With the tip of my cock at her lips I tell her to lick to last remaining drop of cum.

I get off the girl, sit at the edge of the bed and check the time. The girl has cuddled into her mother’s arms for comfort. As Mom is holding the whimpering little bundle of sexy sweetness, stroking her hair and telling her it’s ok I look at them and say “Wow, that was only 35 minutes, we have a lot of time left. The fun has only just begun!”

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