How it started
Introduction:
This is a part 1, Let me know if it is worth posting part 2
I was 34 and had just had a hysterectomy after my third daughter had birthing complications. She was a whoops anyway, I already had a 14 year old son and a 12 year old daughter. I had a great life even if I was not feeling sexy after the baby. The baby was almost two months old when my son, Dylan, brought his friend Zach over. Zach was a nice kid, 14 about 5’8 and athletic. His sea blue eyes and light blond hair I thought for sure he was a girl magnet.
When he was there he kept staring at my chest, it took me awhile to realize why. My normally 36C tits were swollen since I was breast feeding and the tight t-shirt I was wearing were showing it. Other than my tits I was fairly unremarkable, 5’6 with dirty blond hair and blue eyes and the wide hips of a mother. While he was staring my son asked if Zach could stay the night. I told them no problem and went about my business not thinking anything of it.
That night the baby was having a hard time sleeping and my husband had worked late and was sleeping hard. That meant I did not get much sleep. About three in the morning I was up, again, just wearing my bathrobe when I decided to try breastfeeding. About when the baby started sucking Zach comes upstairs, woken up by the crying. He looks at me breastfeeding, and although he couldn’t see anything, he started apologizing. This startled the baby and then Zach did get a good look at my left tit.
I settled them both down and the baby started sucking again. Zach started asking questions, all innocent, he was just curious. Finally the baby was asleep and when I stood up to put him in his crib my robe came open just a little. I fixed it and sat back down next to Zach, keeping him company. He stutters a bit on his next question, he asked about my C-section scar. I explain it and he blushes again for his next question, if he could see it again. I’m normally very self-conscious about it, but whether from lack of sleep or just an appreciation at being noticed, I told him sure.
Leaving the top closed and making sure my crotch was covered opened my robe and let him see my belly. He was in awe. Without thinking he reached over and touched my scar. That touch sent tingles through my body to all the right spots, or wrong spots depending on your point of view. I let him rub and feel my belly as by body responded, it had been a long time since I had been touched like that. As I enjoyed his touch I lost track of the flap of robe covering my crotch as it slid off, exposing me more. My legs were crossed so he did not get a full view, but he saw enough to tell I had shaved.
I probably would not have noticed if Zach had not asked me if I always shaved. I was startled but tried not to show it, I knew I should cover up but did not want the touch to end. I told him yes, that my husband preferred that I did. With an earnest look on his face, but the hardon showing in his shorts giving him away, he asked if he could see. He blushed and explained he was a virgin and had never seen a pussy in real life.
I was flattered in one sense, but hesitant in another more obvious way. He tells me it’s ok if I don’t let him, he understands. Zach then pulls his hand off my belly and that is the breaking point. I tell him he can look, but subconsciously omit the cant touch portion. I uncross my legs and spread them slightly so he can see my pussy, already swelling from his touch.
He reaches over and touches my thigh, again sending tingles through my body. I bite my lip to avoid making a noise. Not a noise to stop him, but a noise of pleasure that might encourage him. Not that he needed encouragement; his hand quickly rubbed up my thigh and felt my pussy lips. He then looks at me, and with a devilish grin, pushes a finger into me.
This time biting my lip didn’t help a light moan of pleasure escapes. I was suddenly horny to the point I didn’t care it was wrong, I just didn’t want it to end. Zach pushes his finger in deeper as I roll my hips to make it easier. He has a huge grin on his face as my robe is completely open and he can see my full naked body. I grab his hand and guide it, showing him how to find my clit and where it feels best.
Before I can cum, he stops and rubs his hand up my body to feel my tits. I’m not sure if he realized that by stopping he made sure I would let him keep playing, I needed release. Zach gropes my tits, which are still sore from being full of milk, before leaning in to suck them. Another groan escapes as he starts licking my nipples. I whisper to him that if he is truly a virgin, then he is a natural. He gives me a slight grin and sucks a bit harder.
Suddenly Zach sits up. My right tit, the one he had been sucking, had started to lactate. With wide eyes he asked if they always did that. I laughed and told him it was only because I was breastfeeding. He leans back and sucks a little more, fascinated. As he gets more into it he is slowly getting more on top of me. Next thing we know he is completely on me, between my spread legs.
Zack kisses up my chest until he finds my lips. After a brief kiss he realizes what happened and blushes, pulling back. I wrap my arms around him and tell him it’s OK. I then kiss him again. I feel his cock pressing against my leg through his shorts. Impulsively I run my hands down his back and push his shorts down. Once he understood what was happening he eagerly moved to assist.
With his shorts off Zach’s cock started poking between my legs. I had a brief moment of second thoughts as reality started to sink in. That ended when his cock found home and he plunged in me as deep as he could go. We both groaned as he did and paused as we got used to each other’s bodies. He whispers that it feels better than he imagined, and I told him to wait because it gets better.
After a couple uncoordinated thrusts we got in rhythm, with Zach sliding in and out of me. With all of the foreplay it did not take long and I was cumming. I never was quiet when I came, this was no exception. I kissed Zach hard trying to muffle my screams. I barely hear him try to say he was cumming too. I feel his cum filling me, making me cum harder. When we finally stopped we looked at each other, realizing what had just happened.
About then the baby started crying. Zack quickly pulls out and his cum started leaking out with him. He pulls his shorts up and I get my robe closed just in time. My husband stumbles into the room having been woken up by the baby. With cum running down my leg I tell him I got it and he can go back to sleep. With a nod he stumbles back to bed. Zach looks at me with a scared look then starts laughing. I pull my tit out, unembarrassed this time, and start breastfeeding again.
Zack blushes and says he should probably get back to bed. I tell him goodnight and asked him not to mention what happened to anyone. I didn’t catch how he replied as he was off, down the stairs. I get the baby to sleep and head off to bed, my thighs still sticky with cum.
The next morning I throw on some actual pajamas under my robe and go downstairs for breakfast. My son and Zach were already down there eating cereal. They stop eating as I walk in. I grab a bowl and sit down with them, they are obviously uncomfortable. It does not take long to find out why.
Dylan suddenly asked me if Zach got me pregnant again. I stared at him stunned while Zach started looking very hard for something in his cereal bowl. I collect myself and explain that I cannot get pregnant again. That seemed to relax them somewhat, but I was uptight. I then asked them what all was said.
Dylan told me all. Zach had spilled his guts and then some. I was about to tell them never speak of it again when they dropped another bombshell on me. They told me they had another friend who wanted to lose his virginity. They wanted to know if I would take it. Dylan pipes up that the kid would pay.
I emphatically tell them no. They respond by saying they guess they will talk to Dad then. That causes me to back down and ask details. They tell me his name is Brian and he is in their class. He was willing to pay five hundred to lose his virginity. Then Dylan looks at me and tells me that he and Zach would keep two hundred for their agents fee.
I was stunned, my son wanted to be my pimp. I reluctantly agree so that they will stay quiet. I tell them to set it up and let me know what the plan is. With that I go back to my room to take a shower and finally wash Zach’s cum from me. Dressed I went back downstairs and the boys greeted me, the plans were already set.
Zach and Dylan were going to watch the baby while at 3:00 I was to meet Brian at this sleazy motel. The boys would tell my husband and daughter that I went out shopping, so I should probably bring something back. That didn’t give me much time to think.
As the time got close I went to change into what I would wear for the “event.” If it was his first time I wanted it to be memorable, but at the same time if I looked more like a mom he might change his mind and I wouldn’t need to follow through. I finally settled in on my khaki skirt and a light green polo shirt. I did go with my sexiest black satin panties and black lace bra. A pair of running shoes finished the ensemble. Zach and Dylan approved of the outfit.
I went to the address they gave me. One look and I decided that if I ever did this again I would spring for better accommodations. It was a roach motel. I went to the room and Brian was already there. He was not a bad looking kid, about 5’3 with mousy hair and petite features. Not bad looking, but no secret why he didn’t have a girlfriend. He was so nervous I felt bad for him; suddenly I wanted to do this just to help the poor kid out.
We introduced ourselves and I asked him what he was hoping for. He blushed and told me he did not know, he just wanted to lose his virginity and know what it felt like. I asked him if he had ever seen a woman before, like walked in on his mom or anything. He mumbles no, just on the internet. I tell him we will need to fix that.
I stand us both up and pull him close. I put his hands on the bottom of my shirt and have him help me pull it over my head. After we toss my shirt to the side I unzip my skirt and let it fall to the floor. I tell Brian to step back and look at me in my underwear. He does and I see the hard-on growing in his jeans. Now a take his hands again and wrap them around me. I tell him to undo my bra.
Like most guys he struggled at first, but I let him learn. When it finally came off he didn’t know what to do. I place his hands on my tits and told him to feel. He did and uttered oh yeas as he did it. He finally leaned in to suck, my turn for oh yeas. Brian was surprisingly gentle for his first time. Again when my tits started milking he stepped back. I explained it to him and he suddenly wanted more. I guided us back to the bed and sat us down.
I pried him off my tit long enough to get his shirt off, then he was grabbing them again. I let him play as I worked on his jeans. Eventually I got them undone and Brian suddenly blushes as I pull his cock out. His cock was shaped almost like a soda can. It was as fat as any I had ever seen, but short, only about five inches. I briefly wondered how it would feel inside me as I gushed and made him feel like it was the perfect cock.
I pushed him back on the bed and pulled his pants completely off. I lick his shaft then try to wrap my mouth around him. I almost couldn’t do it, but once I did I tried to take him all. He was groaning as I bobbed my head up and down. My mouth was stretched so far I did not taste his pre-cum, and much sooner than I expected he was squirting hot stick semen down my throat. I gagged, and then pulled back still stroking him to make sure he came good.
With cum running down my chin and over my hand I look up at Brian, he is almost in tears. I asked what was wrong and he tells me he really wanted to have sex but he came from a blowjob. I smiled and told him it was ok, by cumming now he would last longer when he did have sex. I licked his softening cock clean before excusing myself to clean up. With a quick trip to the bathroom I wiped my chin and tits clean from cum, then washed my hands.
When I came back out, Brian was under the blankets. I smiled at him and asked if he was ready. He shook his head yes so hard I thought it might fall off. I pulled the blanket off and saw he was already getting hard again. I crawled on the bed next to him and stroked him lightly. I pulled my panties off and let him see his first real pussy. I took his hand and guided it between my legs. I moved his fingers up my slit until, moaning lightly, his finger found my clit. I helped him lightly massage it as I explained to him what it was.
After a couple second of that I told him to push a finger inside me. I was soaking wet and he started finger fucking me with ease. I told him how good it felt and to imagine his cock in there. I watched his cock grow as he fingered me. I helped him until I had a small orgasm, then asked him if he was ready to be a man. He muttered a yes but said he didn’t know what to do. I told him not to worry, I knew.
I rolled over and straddled him and sat up so he could see my whole body. I grabbed his cock and aimed it up, then slowly lowered my hips to it. I groaned loudly as he entered me, he was so thick he stretched my pussy. I took a deep breath once he was all in, adjusting to his girth, wishing he was deeper. I moaned to him asking how it felt to no longer be a virgin. He responds better than he imagined while at the same time trying to push deeper.
I started to ride him, feeling this young man slip in and out of me. My tits bouncing as I fucked him faster until Brian grabbed them. He was not long, but he was hitting the right spots, I was screaming as my orgasm built. Then he squeezed my tits hard and I feel him tense up as he shoots a load inside me. The feeling of his man seed shooting to where my womb used to be sends me over the edge, I came hard and loud.
I rode him until we were both spent. Brian was all smiles muttering it was worth every penny. With that I climbed off and started the search for my clothes. The boy must have put a lot in me because it felt like a river coming out. I have everything thrown on the bed before I get dressed and am still looking for my panties. Brian suddenly slaps my ass and when I look at him he is holding my panties and his wallet. He gives me the five hundred then asks if he can keep the panties. I smile, taking the money and tell him sure.
I get dressed sans panties and open the door to leave. As I walk back to my car with cum running down my thigh a young girl, maybe 15, opens the door next to our room. She asks what all the noise was about. I smile at her and tell her to knock on the door, I’m sure he will tell you. Then I leave.
When I get home Dylan and Zach are all grins. As I hand them their cut and head for the shower they tell me that word spreads fast. They already have a waiting list for my services and the price is going up. I sigh and shake my ass at them while wondering what I got myself into.
