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Introduction:

I was shy but helped out my stepmother Jill

First story...more to cum

I am quite young and already I have had lots of trauma in my life. My mom died six years ago from breast cancer. After a few months of grief counseling I was ready to try to move on. My dad had moved on quicker only because his job and dealing with me required it. Then a couple years ago he married a very nice looking younger woman. All was going great until last month when dad got hurt badly on the job. After a week in ICU we lost him. My previous grief counseling helped me along but this was harder, especially for my step mom Jill. Dad was 36 and Jill was several years younger but I really don’t know exactly how old she was. I had school and a part time job that helped me get by but Jill only had a 3 day a week job. Lucky for us Dad had a big life insurance policy and there was a big settlement from work to avoid a lawsuit so Jill could continue working only 3 days a week.

After dad’s funeral it was hard hearing Jill crying herself to sleep night after night. Soon I noticed she would fix herself a drink or two before bedtime. This began to worry me when the number of drinks kept increasing. On the positive side she was sleeping much better.

One night I got home around 8pm after my part time job. Jill was passed out on the couch in only her robe. This was not normal behavior however today would have been their 3rd anniversary. Poor Jill was drowning her sorrows and I did feel bad for her. I also noticed her robe was parted enough to see some leg and part of her boob. At my age hormones began to flow and I walked over to see if she was really passed out. I spoke to her and gently tapped her are but no response. This of course put ideas in my head as I have wondered what Jill would look like nude. I carefully lifted her robe to expose her full boob. I could feel the excitement and my dick growing. I then carefully lifted her robe at the waist and could see most of her white silk panties. I carefully put the robe back down and went to my room for my camera. This was going to be great pictures to jack off with. I turned off the flash, lifted her robe and got pictures of her full boob and her panties. I then got brave and separated her robe to see her crotch. I wanted to touch her but was afraid she would wake up so I just snapped a few more pictures. I got a good close up of her panty covered crotch then closed her robe.

I then gently shook Jill to see if she would respond. I ask if she wanted help getting to bed but she was too passed out to move so I got more brave and horny. I moved one of her legs to the edge of the couch so they were more apart and parted her robe again. I knelt by the couch and I could see her panty covered crotch. I very lightly ran my finger up and down her crotch but still no movement at all. I continued to lightly probe her and could feel her pussy lips and slit. By now my dick was aching for release. I unzipped, pulled out my dick and began jacking off while lightly touching Jill’s pussy. I then put my nose right in her crotch to see how she smelled.

I was in heaven and getting ready to shoot my load. I backed up a little and my load shot all over. Cum landed on Jill’s bare leg and on her robe which freaked me out. I went and got a towel to wipe it off but this caused Jill to stir. She opened her eyes and likely wondered why I was wiping her leg with a towel. I just hoped she would not remember however she pointed at my crotch. I looked down to see I never zipped up and the end of my dick was showing because I was going to use the towel on my dick also. F**k was all I could say and I quickly zipped up. Jill got up and staggered up stairs to bed.

I went to my room to look at my pictures. They were pretty good even with no flash and I had another good jack off thinking about her pussy lips and slit before falling asleep. The next morning I was off to school and Jill was home. When I got home Jill was very apologetic about the night before and promised to cut back on the booze. I went up to my room and found Jill had washed my clothes and put them on my bed. This freaked me out because my tee shirt was full of cum from my late night jack off and her pictures were on my laptop. I looked at my laptop and it had been moved. I opened the lid and there was the picture of Jill’s panty covered pussy. I was so tired and in a hurry to shoot my load last night I had just closed the laptop lid. No password either as I told Jill she could use it if she wanted. Was I busted? Time would tell.

After dinner Jill headed upstairs but came back down in her robe. She then made a drink for herself and turned on the TV. After a couple more drinks she called me in the room to see if I wanted to watch TV with her. I sat with her on the couch and she started asking me about my day at school. I could tell she had drank a few too many. Then the conversation turned personal asking me if I had a girlfriend or not. I told her NO and that I was shy around girls. She turned towards me and continued talking but now I could see up her robe and she did not have panties on. I could see her slit and my dick was growing quickly. She asked if I had any experience with girls so I said none at all but I was very curious. Jill said maybe she could answer any of my questions. I was thinking that I wanted to ask about a blow job, fingering her or sucking her tits as I had heard about all three at school but I was too shy to ask.

She finally said that she had some idea what happened last night. She had seen me with my zipper down and she also had cum on her robe and leg and when she did my wash my tee shirt was pretty crusty. She seemed fine with me jacking off. She also said she used my laptop to check her Facebook page and was surprised at my photography skills. I was in shock and didn’t know how to respond. She said that it was better to get off at home then worry about getting some girl pregnant. She then reached down and touched my leg saying it looked like I needed some release right now. I knew this was the booze talking but I didn’t care. I said ‘Yes’, then sat on the couch next to her and unzipped my pants. She pulled out my dick and began jacking me off. It was great and I shot my load quickly because when she turned toward me, I could still see all the way up her robe to her bare slit. After a quick tissue cleanup she then asked if I have ever touched a girl. I told her I was too afraid but wanted to. She said that the past couple of months had been hard and she also needed some release from time to time. She also said that if this is weird we can stop right now, but of course I said NO and that I wanted to learn all about girls.

Jill had me sit on one end of the couch and then she lay down with her head on my lap. She then opened the top of her robe to uncover both of her perky boobs. She told me to go ahead and rub them because girls liked that. I very carefully put my hand on one of her boobs. It was very soft and warm. After a minute or two Jill told me I needed to be a little firmer. So I began to squeeze them both and rub a little harder and I could tell she liked it. Next she had me play with her hard nipples while rubbing. We were both getting into this and I could hear her soft moans. My dick was beginning to come to life again also. After several minuets Jill reached down and opened the lower part of her robe showing me her pussy. She spread her legs and then took my hand and moved it down and had me rub her pussy. It was soft, very warm and wet. After another couple of minutes she took my middle finger and rubbed it up and down her slit. She had me explore her slit, find her vagina and stick my finger in, she then had me find her clit which took me a little time. When I did find her clit she had me just lightly rub circles around it. It was just a little hard bump at the top of her slit but I could tell she really liked it when I rubbed it. By now I had a bad hard on again. I could not believe I had my fingers in a girl’s pussy. After just a few minutes Jill arched her back, moaned and put her hand on mine and just pushed it tight too her pussy. I could feel her pussy pulse several times and then Jill just relaxed.

She said that I was a natural and it was a great orgasm, much better then fingering herself. When she sat up my dick stuck up like a flag pole. Jill looked at it and joked saying ‘Houston we have a problem’. With that she lay back on the couch but on her stomach this time. I got to see her nice round ass which was great. She took my dick and slid her mouth over the top half. I almost shot my load right then but held back the best I could. It felt so great having my dick in her warm mouth. I reach down and rubbed my hand over her ass cheeks. She had a really nice firm round ass. A few more bobs on my dick and I could feel it building. I moaned out load and kept feeling her ass with her mouth on my dick. I unloaded again and Jill kind of spit out my cum and it ran down my dick. I didn’t care because it had to be the biggest load I have ever shot…rope after rope shot out until I was fully drained.

She got up, took her robe and wiped up cum, and headed upstairs. I could hear the shower going and I wondered how awkward dinner was going to be. I went in the downstairs bathroom and also cleaned up. She came back down in a pair of tight jeans and top and started cooking dinner. Soon she called me to come and eat. I hated being so shy because I just did not know what to say. When we sat down Jill smiled and said that she had a very nice time earlier. I told her that it was the best day of my entire life. She just grinned and said good. We chatted about school and her job some and I headed up to work on an essay for school.

The next couple days were busy for both of us. I jerked off each night looking at the pictures I took of Jill’s pussy and thinking about that blowjob. On Saturday night after dinner Jill said she had an idea I would like. I said great hoping it involved her mouth and my dick. She said that she stopped at the mall and got some new sexy underwear and wanted to know if I wanted to see it. I quickly said yes and asked if this was going to be a Victoria Secrets fashion show. Jill just grinned and said ‘Yes I guess it kind of is’. I asked if I could bring my camera and she said sure, I must need some new pictures anyway.

Although I thought she was drinking less the last few days I could tell she had mixed a few tonight. I didn’t know if the drinks made her horny, lowered her inhibitions, or both but I didn’t really care. I went up to my room and put on a pair of sweatpants I had cut off to make shorts and a clean tee shirt. I also removed my boxers and quickly washed up. I then headed back to the couch with my camera. Jill soon called down saying the show was starting. She came down in a matching bra and panties carrying a Victoria Secrets bag. She come over in front of the couch and twisted and twirled around while I clicked away. She was so sexy in just a bra and panties and I was rock hard by the 2nd outfit. She had such a cute round bubble ass. After three or four showings Jill comes out topless saying she had gotten more panties then bras. My camera and my eyeballs were getting a real work out. After only fifteen minutes the show was over. The last trip out Jill was completely nude. I clapped and whistled and she just grinned. I noticed she had made another drink a bit ago and at the end was getting a little tipsy.

She came over to the couch knelt down and stuck her hand up my shorts and found my hard dick. It did not take long for me to shoot my first load. Jill told me to just take off my wet shorts. She said it was now her time and plopped down on the couch next to me. I asked what do you want and she said how about 69. I knew what 69 was but I didn’t really know how to get in a good position. Jill had me lay on the carpet and then got on top of me facing the other way. This put her pussy and ass right in my face. She told me to find her clit with my tongue. She then put my dick back in her mouth. That felt so good I did my very best to find her clit. It took a little exploring but I guess she was liking it and I sure was. It took longer to blow my second load but when I did I felt Jill tense up, her clit got harder and her pussy started pulsing and leaking juice. My face was all wet as was Jill’s. She just rolled off me and moaned. I told her that I liked 69. She just smiled and lay on the floor for a moment just breathing and saying nothing.

We got up, got changed and she began cooking dinner again. As the food and time began sobering her up she started apologizing for her behavior. I quickly stopped her saying how much I appreciated her and the lessons about what girls want and like. I told her she was greatly helping my shyness and fear of talking to and being around girls at school. She just smiled and we chatted while finishing dinner.

I have to admit this was getting to the point where all I thought about was putting my dick in her pussy. Fortunately I had a couple dozen new pictures to jack off to. I would rather have Jill jack me off but for now the pictures worked just fine. I just wished I had a good close-up of her bare pussy. It is so sexy all puffy and wet and I just wanted to, as we say in school, lick it and stick it. I assumed if I had a chance to really fuck her it would be when she is pretty drunk. I guess I did not care at this point, as for me it would still be great.

I did think it was odd she showed no interest in getting to know other men. When I asked her about it she just said it was too soon and changed the topic to me and girls at school. I told her they were a pain and even mean at times. She just laughed and said she remembered what high school girls were like.

We had a very uneventful week but on Sunday Jill was again in a very sad mood. It would have been Dad’s 37th birthday. I still didn’t know how old Jill was and when I asked she just said ‘old enough’. She looked ten years younger than Dad but I think she was getting close to thirty and just looked younger.

It had now been four months since Dad’s funeral and both Jill and I were doing much better with the loss but Jill would still have these bad days from time to time. I saw the booze come out around noon and I decided to finish some homework. She would make me sad as well if I hung around her today. After a couple hours I went downstairs to find Jill looking at photo albums of her and Dad. The bottle of gin was almost gone. She looked so sad I went over and sat next to her. She was pretty drunk but happy to see me saying I have been a big help to her the past few months. I told her she was the same for me.

Jill slouched over and put her head on my shoulder. We both had on sweat suits, the normal for a Sunday afternoon to just relax. After a few minutes I put my hand on Jill’s leg and started to rub it moving my hand higher and higher to see if Jill was in the mood to fool around. She responded by going right for my crouch and finding a mostly hard dick. I moved my hand higher and she parted her legs letting me rub up and down her pussy. I could hear her breathing pick up and hoped I would get lucky today but she was drunker then I had seen in a long while and quickly seemed to pass out.

I got up and took a blanket that was over a nearby chair and spread it on the couch. I then laid Jill down on her back and told her I would give her a massage and she could sleep. I got her around on the couch and knelt on the floor next to her rubbing her legs. She just moaned thanks and seemed to again pass out. I was very bold this time and reached under her top to find those perky tits. After rubbing and feeling them with no response from her I raised her sweatshirt enough to suck on her nipples. I had wanted to do this but was afraid to ask. While I was sucking on her tits I slipped my hand down her sweat pants and found her pussy. I was so warm and soft I just felt all around checking it out. I began to have thoughts about fucking her again. I went behind and couch and got another blanket and put over Jill but while doing it I pulled off Jill’s sweatpants. She roused a little mumbled something and passed out again. I went and got my camera, came down and lifted up and bottom of the blanket. There was her pussy again. I spread her legs and took a couple close ups then licked my finger, stuck it in her pussy and took more pictures. I was getting really worked up and went back to her room. After looking in some drawers I found a dildo and some lube. I assumed she was using something and even heard her moaning once or twice late at night. I went back to the couch, lightly lubed the dildo and put it in her pussy just a little way. She again didn’t move and I got some really cool pictures. I carefully and slowly put it in almost halfway but was afraid to go more. Still she was out which I found hard to believe but I got more pictures.

I thought that this may be my only chance to fuck her even though I felt bad because she was so sad and mostly passed out. I convinced myself that she would want to fuck also but was holding back because I was her stepson. Finally I could not stand it any longer. I slipped off my pants, lifted the blanket and lay on top of Jill. She started to move a little and I thought I heard her say my dad’s name. I slowly began to slip my hard dick into her lubed pussy. She opened her eyes for a second then put her hands on my ass and pulled me mostly inside. She just said ‘It’s OK’ and opened her legs some more. I began to slowly pump away in that hot, wet pussy pushing my dick in as far as it would go. Jill moaned a little and seemed to be ok with it. After a few more deep thrust I could feel me getting ready to cum. I held off for as long as I could and then began pumping load after load of cum deep into Jill’s pussy while experiencing the strongest climax I have ever had. Jill opened her eyes again and again just said ‘It’s OK”. I got up, put the blanket back on her and turned on the TV. That was truly great; I just hope Jill was really OK with it. I began to feel a little nervous knowing I would find out how she felt in an hour or two when she woke up.

Three hours later I was out in the kitchen making a sandwich when I heard Jill say ‘Hey’. I turned around to see her standing in the doorway back in her sweatpants. I just said hi and braced myself for a lecture or worse. I suppose she could claim I raped her or at least took advantage of her if she remembered that I fucked her. She just point blank asked me if I fucked her. I was so taken back and emotional I just shook my head yes with tears forming in my eyes. I was sorry for how this happened even though I enjoyed it very much. To my surprise she mumbled something about being all her fault for messing with my hormones. I went over and hugged her saying I was very sorry I let this happen but I just couldn’t seem to stop myself. She just said ‘don’t worry about it’ turned and went to bed.

The next day was no school. Jill didn’t come downstairs until 10am and had a hangover to boot. I still felt bad and wanted to talk this out. Jill just said that she really started all this by just missing sex so much. She wanted me to forgive her. I was shocked and said it was me that needs to ask forgiveness. Needless to say neither of us blamed the other which worked out ok. I did however want to fuck her again sober and hoped she would want to.

That night I decided to talk to Jill again and see if she wanted to lay down some ground rules. She thought that ground rules were a good idea. First let’s keep fooling around to one night a week maybe Sunday. I was shocked but glad as I was afraid I was going to get cut off. I asked if I could get some lessons and try a few different things. Jill was OK with that after all we had already fucked. This began sex class every Sunday after dinner. Because we had already fucked Jill did not mind fucking again as long as she could teach and show me how to do it right. We were to continue lessons until one of us wanted to stop or began a serious relationship. I said ‘GREAT’. Well I learned a lot. I had many lessons on how to go down on a girl and lick her pussy. I learned about the doggy and missionary positions. When I asked about anal Jill said she had never tried because my dad’s cock was very thick and it looked painful. My dick was not very thick or long. I assumed it was average but after checking the internet I found it was just a little on the small side. I just let it go but Jill decided at one point to just try it. She did an enema first and I put on a condom and lots of lube. I thought fucking her nice round ass would be great and for me it was good. Jill however didn’t seem to like it as well as me and that was OK.

We fucked and sucked every Sunday night for over a year before I went off to college. When I came home for break I brought a girlfriend home only to find Jill had also met someone. We just hugged, smiled and had a very nice talk. When we were alone I again thanked Jill for how much I learned and how useful the information was. She just smiled and reminded me that it got both of us through a tough time in our lives.

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