I personally don’t mind having sex when I have my period, and most boyfriends I’ve had in the past don’t mind either, but my current one is a bit squeamish about it, so he prefers to just do anal when it’s that time of the month. I think he’s being ridiculous, but it is what it is. This past weekend we had some anal sex and I can’t say I don’t cum from it, he’s quite good at it, I think every girl he’s ever been with he’s said no to for regular sex when they have their period, so he’s had lots of experience with anal sex and knows how to at least make it pleasurable for both parties.
He likes me on all fours and I can rub my clit in that position or hold a toy on my clit when I’m like that and he eases the head of his dick right inside my tight ass and then eases it in all the way up to the balls. He likes a smooth ride, so uses lots of thick lube, the kind that’s specifically made just for anal sex and doesn’t usually need reapplication. He grabs my tits or even holds the vibe on my clit for me, which is usually plenty juicy, the way I buck my hips back and forth, the vibe hits my clit just right and I usually cum within a couple of minutes.
When we fuck the regular way he also enjoys doggy style, he always said that my ass was one of the things that first attracted him to me, and I know it’s a bootylicious one for sure. I don’t mind a good spanking when I get fucked either, so my ass has many purposes, lol. His cock isn’t that big, but it’s big enough, so it doesn’t hurt me when he does go to town for some backdoor fun. I can take it just fine.
This caller this week is into crossdressing, not an uncommon topic by any means, quite common, actually. He’s explained to me he’s different than other sissies in that he has no interest in forced bi, sucking cocks, or anything to do with men at all, he said if he could turn into a woman, this is what he wants. He’s still attracted to women though and wants relations with women, so he’d be a lesbian. Many men that want to be a woman are attracted to men, but he was clear he was not, he loves women and loves to service and lick their pussies. Something most true sissies I’ve talked to really don’t want to do at all.
Many sissies that have called are in fact intimidated by women and couldn’t fuck them even if they had the chance. Many have said they have no experience with women whatsoever and fantasize about rubbing their “willy” against another sissy until they squirt their sissy cream together. The thought of penetrating a woman and being in any way dominant is abhorrent to many of them. A few like both men and women and claim their girlfriends put makeup and wigs on them and paint their nails, but honestly, I’d think a girlfriend like that would be nearly impossible to find that was into that.
So sissies often suffer alone and have physical contact with no one other than their own hand, since they may not want a man, but only another sissy, or women are scary and demanding to them and they cannot handle that. Some have called to give elaborate descriptions of what they are wearing, things they got online, life since online shopping has made shopping a lot easier for the sissy or crossdresser. Imagine only a few decades ago the awkwardness of going into a physical store and having the clerk know what your plans were and judging you, yikes.
Recently I went to an Oktoberfest evening and everyone there was drinking, including me, and somewhere along the way someone must have slipped something in my drink, since things became foggy a while into the evening. There was several men sitting at the table that was that I didn’t know and when I got up to use the restroom, I’m sure that’s when one must have put something in my drink to lower my resistance. I was dancing with some people and parts of the evening I just don’t remember.
I was led into some room, I think it was the coat room, or maybe it was the room behind the stage the band changes in and keeps their instruments in, and there was a table back there and I recall being laid on the table and my clothes stripped off and someone getting on top of me, I tried to say no, but I just couldn’t fight them off, my limbs seemed to be made of lead. I said no, but I could feel someone’s cock penetrate me, it was all a blurry haze.
It wasn’t that it didn’t feel good, but I didn’t want to have sex with whoever it was that was doing it, but I had no say in the matter, I just felt my pussy getting used, getting fucked, getting filled. I was left there naked on the table, I had the strength to get dressed, and get a cab home, but it was all dreamlike. I don’t know who to blame or who did it or anything. It wasn’t what envisioned for the evening at all, but I guess if I’d not left my drink unattended it wouldn’t have happened. I’m sure I’m not the first woman something like this has happened to.
I know it’s not right to abuse one’s power they have over employees in the work place, but sometimes power just overtakes you, like a drug, and you cannot help yourself. I’m a CEO of a medium sized successful company, and I have contact with lots of different staff over the course of a day. One young man that was hired recently is quite handsome and I knew I shouldn’t show an interest in him since I’m his superior, but I couldn’t help myself and I asked him to stay after work and we had a meeting.
I told him he was in danger of being let go, not true, and that if he wanted to stay, he’d have to “go that extra mile” and show me how much he wanted to keep his job. I felt guilty doing it, but I did anyway and he was most eager to please me and keep his job, so he asked what he could do, and I said licking my pussy would be a good start. He looked a bit surprised, but not unwilling, so he crawled under my desk and adjusted my skirt and panties and went to town with his tongue on my pussy and he was pretty good at it as well. I told him I might need this sort of “help” a few days a week. He seemed ok with that arrangement.
This went on for months and I decided I wanted more and more of his attentions, and he was willing and able to meet every one of my orgasmic demands, and he proved to be a good lover, and I was asking him to stay late after work and having him come to my place on weekends. I’m sure how this will all turn out, but I’m certainly having fun in the meantime in any case.
Just when you think you have heard every weird thing out there, another guy tells you something new. This caller asked if I’d ever had those little green plastic solider G.I. Joe toys as a kid and I said there had been some floating around at one point. Then he said he likes to take those tiny army men and get this, go into public women’s bathrooms and dump some in the toilet and think of the women peeing on them. I really didn’t know what to say to that.
All I could think of was potential plumbing disaster from flushing something that would not break up and clog the pipes. He wanted to know what I’d do if I walked into a bathroom stall and saw them in the toilet, I said I’d go into another stall. Then he said he snuck in and dropped around 20 of them in a toilet at the mall, I couldn’t believe my ears thinking he imagined some women going in, seeing them and going pee as she’d expected to then they would get flushed. It was all quite bizarre.
He wouldn’t be witnessing it, or spying on them, just the idea of it happening was what got him going. He didn’t seem to care for my more practical concern of plumbing disasters and seemed to want me to say oh yes, I’d piss on those soldiers, alright. LOL. I’m not quite sure if he has a grudge against the military, or where this odd fixation comes from, but it certainly stands out among calls I’ve had. Men have mentioned Barbie dolls a few times and even stuffed toys they are rubbing themselves with, but little green army men is a first for sure.