Masturbation female solo? Yes! Of course! You should have seen the state this discussion had me in.
We had ‘experimented’ a little, I suppose. Once, while I was riding him, he unclipped my trainer bra and it fell across his chest. I suppose I realised at the time that this was important…had significance….because I felt him grow inside me, and he became, at least in his movements, softer, gentler, more…feminine. It wasn’t until after he got engaged to my sister that we recently had this discussion. The Lovely Chris (TLC and I still chat…still speak of sexual things…but we both know he’s a no-go area for me now. Don’t ask me why…it just feels like it’s the right thing to do. Maybe that will change, but for now, that’s the way of it.)
“So…when did you realise you liked dressing up in girls’ underwear?”
(Huh? Who said that? Shit…I did. Why? What the actual fuck? Thanks Miss Brain!)
He looks serious as his mind tracks backwards in time.
“I suppose from when my sisters became…umm private. Up until then, we goofed around, thinking nothing of skinny dipping, or being naked around one another, but then….then it felt like…oh, I don’t know..like Kat and Jess had joined some secret club that I wasn’t a part of…couldn’t be a part of.”
(Oh boy…what a weight of sadness there was in that!)
“Jess was 15, and Kat was 16. I was used to seeing them pad around the house in bra and panties, but suddenly…overnight, it seemed, that all stopped. Now they were….ummm…secretive. So… " (big sigh, and a bigger pause) "so one afternoon, when I had the place to myself I went into their bedroom. I remember it was a stiflingly hot afternoon…one of those days when even breathing deeply makes you tired and sweaty, you know? I don’t know…didn’t know…what I was expecting to find there, but….it felt….female…you know? There was a light, feminine smell to the room, and unlike my room, this one was spotless and tidy. Two beds…two Ali Baba washing baskets, a double dressing table, and their en-suite bathroom was also immaculate, but in the cupboard under the sink, I found sanitary pads s and tampons. I took one of each.”
(He pauses again…reflecting on that afternoon. Miss Brain clapped her hand over my mouth and hissed ‘Shut the fuck up’. Let him remember…let him think.)
"I mooched around. I remember, I sat on Kat’s bed….I think I might have lain down on it for a while. Then I opened Jess’s laundry hamper. I found myself looking at her bra…..I took it out and held it. Nothing special…just a soft, cotton trainer bra….a bra I’d seen a hundred times before, but this time….this time, it smelled…kinda sweaty, but a good sweaty, if you know what I mean. Then I opened Kat’s hamper. Right on the top, a pair of pale blue panties. And boy, we’re they wet. The crotch was heavily stained with this whiteish creamy looking stuff. I remember smelling it and it made me dizzy….really dizzy. I had to sit down back on Kat’s bed. I don’t remember having any overtly sexual thoughts though. I mean, I didn’t think of fucking either of them, but I did know this was part of their secret world…a world I really wanted to be a part of.”
(He pauses again, for much longer this time. I hoped he wasn’t editing his thoughts. I wanted pure, 100% honesty.)
“I don’t recall going back to my room, but I must have because the next thing I remember is being in there, sitting naked on my bed with that bra and those panties. I remember putting the bra on, and then, very slowly, pulling the panties up my legs. Of course I had to do something with my raging hard-on, so I just let it lie flat on my belly and pretended it wasn’t there. When I felt Kat’s wetness against me, a big glob of pre-cum came out of my cock. I think that’s when I joined the dots. Pre-cum….or maybe just cum. That’s what was on Kat’s panties which were now against my balls. I lay on my bed and spread my legs which only pulled them tighter against me. I really wanted to be them…be some amalgamation of both of them. All the time, my cock was leaking like crazy. I stroked my nipples through the bra, and more pre-cum flowed from me. Then I pulled Kat’s panties aside and imagined I was showing my pussy. I stroked my balls, but as if they were a cunt, you know? I…..I even pushed the tampon into my bum….just a little way. I touched my bum pretending it was a vagina. Sometimes, I’d put the sanitary pad in the panties and pretend I was on my period. Anyway, as soon as I touched the head of my cock, I came….really hard. I only did this a handful of times, but oh Anna…it drive me crazy.
He looks like someone who has just been to confession and rid himself of an awful sin…or, in this case…a secret. “I used to ‘borrow’ their underwear from time to time….not to be sexy with…I mean, not to smell either of them, but I just liked being in their club for a brief time.”
(Miss Brain sensed something.) “Honestly? Did you never smell either of them on their panties?”
“Well…a couple of times….yeah. Oh Anna…you’ve no idea how smelling a girl makes a teenage boy cum!”
(I do, actually!)
“The whole thing feels so…so….dirty.”
"Did they ever find out what you were doing?"
“No. I was very careful. Everything put back exactly as I found it.”
If the situation had been any different, I’d have had him in my bra and panties right there and then. As it is, when he left, I engaged my ‘role play’ button and masturbated, pretending I was him pretending to be me. With the exception of a distinct lack of semen, the orgasm was very, very satisfying.
There’s a lot to be said for role play, but his story about feeling shut out when his sisters reached what nuns call ‘the age of discretion’ was quite sad.
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