A very understanding mother.
A few weeks after I got home from the Army in 1965 I was living with my mom and two of my sisters. One sister moved out about two weeks after I got there. One day home alone I got the idea to check out my mothers clothes. She had a very nice assortment of skirts and lingerie even nylons and garter belt. So I decided to strip off my clothes and try her stuff on.
I had got all of the stuff on, a pair of her panties, half slip, a red skirt and a black sweater and the garter and nylons. The sweater was a little small for me but it did the job. The skirt was a sheave one with a zipper and button in the back, so I put it on and fastened the button and zipped it up slid it around my waist and it fitted perfectly. The skirt came just above my knees and I was ecstatic!
I was having a grand time feeling very feminine and didn't have an erection and looked in the mirror and then sat down crossing my legs which I had seen her do for my whole life. I was at this for about forty five minutes when I heard my mother's car door slam and then the kitchen door open and close. I had no time to get out of her clothes so I just decided to sit on her bed, nervous as hell and take my medicine.
Her feet were clomping along the wood floor and she said as she was walking towards her bedroom, 'Mike are you here?' I said that I was, waiting for her to see me dressed in her clothes. She takes a surprised look at me! She giggles and says, 'Stand up and let me look at you!' So I did with my legs nearly giving out from under me. She smiles at me and says, 'If your hair was longer you would look just like a girl!' She puts her purse down and clucks to herself.
I then asked her if I could sit back down and she says, 'By all means! She says. 'Are you mad at me mom?' 'No I'm not mad just surprised. I'm more intrigued by this more than anything.' She is checking me out and starts giggling again. 'Should I get out of these things right now?' I said. 'No you don't have too you can stay like that for a little while.' I started to relax and crossed my legs. 'Don't forget to keep your knees together when you're in a skirt ok?' She says with a little smile. 'Do you have on a pair of my panties too?' I nodded. 'Well ok, do you like being in a skirt?' I said that I did and it felt great. 'Is this something that you want to really do?' She says without smiling. Yes I do I said. 'Well ok then.' She says. She goes to her closet and searched around on the floor and comes out with a pair of red high heels. 'Here try these on!' The pumps were a little tight and she had me stand up and walk around. It was a little awkward at first but then I got the hang of it and she said 'You're going to need a pair of heels that are a size bigger than mine.'
'I'm ok with this Mike but make sure you don't go outside or get caught by Connie.' I told her that I would be careful. She steps towards me and puts a finger in the waist band of the skirt. 'That's good the skirt fits you perfectly and I have to admit Mike that it looks good on you. All of my skirts are the same size so I have some others you can wear too!' We're going to have to do something else about your blouses and sweaters but I'll leave that up to another time. I'll take you shopping with me!' She then goes to her jewelry box and gets out a pendant and puts it over my head. 'You want to try on my earrings while you're at it?' I did but the earrings hurt after a bit so I took them off.
She looked at her watch and said it was time to get out of her clothes. It surprised me to no end that she just stood right there. So I took off the skirt and she sees the slip of hers, a beige half slip with lace on the bottom. 'That looks real sexy on you Mike!' 'I know it feels sexy on me too mom!' I was starting to get hard and was shy about her seeing my erection. So I hesitated and she looks at me and smiles. There was no way she couldn't have seen the bulge under the slip. 'Well Mike you have to take off my slip too I want to see what pair of panties you have of mine.' I was wearing a very sheer nylon white pair with lace on the leg openings.
'Ok mom! I said taking the slip down and stepping out of it she puts her hand out and I hand her the slip. Then she starts turning nearly beet red seeing me with an erection! She gasps and says, 'Well we're a little bit excited now aren't we?' 'I couldn't help it mom!' My voice sounding like a frog. For sure I thought that she would turn and walk out of the room. The head of my dick was clearly showing through the sheer nylon. She puts her hands in front of her standing there normally still holding the slip. She seemed to be mesmerized by my cock. She looks at it then up to my eyes than back down to it then back to my eyes. She says with a teeny smile, 'Well I have lots of that kind so you keep those with you ok?' I said I would.
It felt great to have an erection and her checking it out. She folds the slip and steps over to her dresser. She turns around and leans back against the dresser. 'Well the garter belt fits too I see!' 'Yes it does but the nylons seem kind of itchy.' 'Yes they itch a little on me too!' She says looking down on them. 'Did you roll them up you've seen me do that remember?' I said that I did and it was something I never got tired of watching her do. My dick was now starting to throb and to pulse against the panties. She looks at it takes in a deep breath of air and says, 'Just try and relax Mike ok I understand! Take off the sweater for me I want to hang that up!' I took off the sweater and handed that to her and she takes out a hanger and puts it back into the closet.
I was beside myself thinking how she was just going about her chore without being upset with me. 'So mom you seem to be ok seeing that I have an erection!' She smiles at me and says, 'Yes I'm ok with it!' She checks it out again. 'Should I get out of the panties now?' 'Yes you should, Connie may be here anytime!' 'Aren't you going to leave the room?' I said. 'Do you want me too Mike?' No I said. 'It's not the first time I have seen an erection!' She says again looking at my cock. 'First you need to unclasp the nylons and role them down so you won't get a run in them!'
So I sat back down on the bed and did the front ones first and I had to reach behind me for the back ones and it made my dick thrust out even more than it was. When I did that my cock started spewing out my jizz. My mother lets out this tremendous gasp and blushes again and puts her hand over her mouth saying, 'Oh dear me now that is a surprise!' 'I couldn't help it mom!' Her eyes were riveted to my cock shooting the cum out of it. Some of it came through the panties and made a huge wet spot. I got real embarrassed and said I was sorry and it just happened with all of the excitement. She then says, 'Don't tell anyone that this happened, it's just between you and I Mike get yourself dressed and help me with the groceries ok?'
While I helped her with the bags she was looking at me and smiling. I was still feeling the after effects of me cumming in front of her. She says, 'I guess you're not my little boy any more Mike!' I said, 'Mom I'm sorry that happened!' She says very calmly, 'It's ok Mike it really is. It happened and I can deal with it.' 'What does that mean mom?' I said wondering. 'Well Mike.' as she sets a bag down, 'I don't know what it means but rest assured it wasn't a bad thing for me to see you climax that's all.' She gives me this funny smirk and says, 'After all I've seen them cum before too and as long as you don't wave that big horny thing of yours in front of me we can continue ok, now here help me put this stuff away ok?'