That worked out well part 1
Long story short I am a widower and my wife's mom lives with me to help look after my children, My mother in law works in an undustry where she is able to work flexible hours and if need be she can work from home as much as she wants and only goes into the office once or twice a week now.
When I married my wife her mom was 43 and right from the day I met her she could have easily passed for my wife's older sister so there is something to be said for getting knocked up at 17, A our wedding many guys my age were asking who she was and so on and a few tried to pick her up, Thankfully none succeeded. If they did their hair the same they looked VERY similar and often shared clothes. Three weeks after first meeting her I got to see how similar they actually are when she had a nip slip, Six or so months later I seen up the leg of her shorts while helping with yard work and seen that even though she doesn't shave their p****** are basically identical.
My wife never met her dad, Her mom would never tell her who he was or anything about him and I suspect from a couple very drunk conversations with her uncle that maybe her mom doesn't know exactly who it is (She got around in her teen years). After my wife's passing she went into a bit of depression which is understandable but she seems better now, We attended a christmas party with some family and walked home, The kids had stayed the night with their cousins so it was just us. We talked and walked home and when we got home she went downstairs to her room and I sat down to watch some tv.
I was sitting there and she came upstairs, We had both been drinking a fair amount and she NEVER goes braless in front of anyone, EVER, but she was wearing just sweat pants and a t-shirt and obviously no bra, I was...Tipsy and jumped at the chance and when she was in the kitchen getting a glass of water I walked up behind her and put my hands on her hips, I knoW for a fact she hasn't even dated let alone gotten f***** in 17 years, Whether or not she f***** any of the guys she dated before that I have no idea but when I put my hands on her hips she took a quick, Deep breath and I leaned in and kissed her neck and she swallowed hard and made a little noise.
I figured I had the upper hand and just went for it, I slid my hands up her shirt and cupped her b**** which was when I realized why she never goes braless, She gasped and tensed up and her body shook a little bit then she grabbed my hands and pulled them away saying "Whoa, Whoa, Whoa....Innapropriate" and grabbed her water and basically ran down the stairs. I stood there thinking "Well....I f***** that up". I went to my room and got undressed and got into bed, I was laying there thinking about how nice it felt to have a pair of t*** in my hands even if they were soft and saggy and was laying on my back stroking my d*** when I heard "Ahem..." I looked up and said "Oh s***...Sorry" She said "What was your train of thought there...Well...I guess I know what you were thinking" as she motioned to the bulge under the sheets, I said "I am so sorry, I just, You looked so good".
She was visibly uncomfortable with my comment and she stuttered and stumbled for words and she stood there with her nips showing through her t-shirt and then said "Soooo...You thought you would just what...Do me at the kitchen sink?", She came in and sat on the side of the bed and said "I think we should talk...I understand how it can be hard" then she paused and said "Difficult...For someone to go from sexually active to not just like that, But...I don't think you are thinking clearly right now and your...Advance was ill timed".
I wanted to say something but I couldn't even get one word out until she looked at me and said "What are your thoughts?", I took a deep breath and said "I just...I don't know, You are a beautiful woman, I know you haven't...Ya know...In a while and thought maybe we could help each other out a bit", She stared at the wall and pursed her lips, Thought for a second and said "I don't...Um...That sort of Help is not what I really need", I sat here staring at her nips and thn she looked at me and said "But...I'll tell you what, If you need that sort of help maybe I could do...Something to help you".
Ok, I'll be honest, I almost came right then and there and she sat staring at the wall possibly regretting her choice at that moment but I wasn't going to let it go to waste and said "Ok", She looked at me and was making some weird faces and was lost for words then she closed her eyes and reopened them and said "I don't know...What...To...Do". I pulled the blankets down and she looked at my d*** Took a deep breah and then nodded her head and said "Good gawd", I said "What?" and she said "I didn't realize...I mean, I had no idea you were" waving her hand at my c*** and I said "That I am????" and she said "Ahem...That big". Now not to toot my own horn but I am 8" long, Quite girthy and circumsized.
She said "I don't know, Um, I just, What do you want me to do", I said "Just stroke it and let's see where it goes", She gulped and reached for it nervously and pulled her hand back a couple times before grabbing my shaft and she sighed and said "Holy crap", She just kept shaking her head and basically inspecting it, Looking at it and moving it around to get different angles and then finally just started stroking it squeezing it pretty hard, I grabbed her hand and said "Slower", She was so tense and nervous and awkward and I was loving it. I put my hand on her leg and she stared at the wall, I started massaging her thigh and moaned a little, She was doing a terrible job but it felt so good to have someone elses hand on my d***.
She tried to switch hands and reach across with the other hand but it was all awkward and she stood up, Crawled over me and laid on the bed with her head about at my stomach and started stroking me again, I put my hand on her back and lifted my hips, She pulled away and I pushed her closer and she said "No" then she rolled on top of me and straddled my right leg and sat on it, She started stroking me with both hands and after a few minutes she stopped and said "Is this going to work?", I shrugged and said "Could you take off your top?", She squinted and looked at me then said "I don't think, You don't want to see that", She was still stroking me and leaning forward and I reached over and cupped her one b*** through her shirt and then grabbed her shirt and she took her hands off my d*** just long enough to let me pull her shirt off and toss it on the floor then went back to two handing it, I moaned "Oh god you have nice t***", She scrunched her face but kept going, I cupped her b**** and rolled her nips in my fingers and they got instantly hard, She was stroking me and she spread her knees sitting a bit harder on my leg and then as I watched her face I could feel my leg getting hot, She stroked a bit faster and scrunched her face up then she moaned and her groin twitched, Her stomach flexed every time she moaned and then I couldn't help it, I tried to hold it but I started c****** and her hands got slippery and I came more and she stared at my c***, Her body started shaking and I swear to god I felt her come on my leg, My leg got wet and she shivered and lifted her crotch and then sat downa nd ground her p**** on my leg and moaned "Hoooo fuuuck, Oh f*** yes, Yes, Yes" and moaned, I just kept coming and coming and my leg was wet from her and there was come all over her hands, Her saggy little b**** were jiggling and She clenched her thighs and slowed her stroke, She literally milked my d***, She squeezed at the base and squeeeezed out the last drops of come and then pulled her hands away and looked at them dripping in come.
I wiggled out from under her and grabbed a hand towel and gave it to her, She wiped her hands and laid down gasping for air and was panting hard, She spread her legs and her sweats were soaked like she peed her pants, She groaned and said "Oh god, Ooooohhh", She took her cummy hand towel and shoved it in her pants and wiped her self with my come and pulled it back out, I knew she was going to bolt and I quickly pulled the blankets out from under her and went to cover her and she said "No, Just, I just need a minute", I said "Here just, Let me get you something else" and I grabbed her sweats under the blankets and pulled them down, She crossed her ankles and said "Whoaaaaa, No, No" I uncrossed her ankles and pulled them off and said "I'll get you something else" and she looked panicked, She was now naked and couldn't bolt so I went into the bathroom and looked around for something to give her to wear while I looked at how wet her sweats were.