More Kinky Masturbation Ideas, So Things Don’t Get Boring

The Pantyhose Mermaid and Silicone Dildo accessory

So there you are all dolled up in that skimpy dress, favorite pantyhose and super tall heels and you can’t resist what is looking back at you in the mirror. It gets just a tad boring though with the hand to penis thing that you’ve done for, oh, the 10,000th time in your life. You’re a crossdresser for God’s sake so you are use to an alternative sexual lifestyle.

Why not explore this further? I’ll even let you have a look at my little bag of tricks. Here’s one of them if you haven’t seen it yet but I’m sure you’ll have some fun with these others.

Silicone Dildo

Yes, just like in the image above (though I don’t know if they are around anymore). These seem a little weird at first and, yes, it does hurt the first time if your back door cherry hasn’t been popped yet. Yet, after each successive session a dildo actually becomes very enjoyable leaving you with that satisfying “naughty” feeling, like your parents caught you crossdressing or you just had sex with a transvestite.

The real fun with the dildo, though, is the challenge of seeing if you can get it all the way in. Yes, I was able to get the one you see above (about 8 inches) all the way up my love tunnel after a few tries (and lots of lube). I was elated when it did and now I’m possibly ready for my ass to take on hot tranny dick… oh the possibilities! Just remember, use a lot of lube.

There is of course a downside to using one of these monsters… getting cookie dough on it. No, it’s not fun to clean up and you are guaranteed to be turned off by it. So to prevent the doughy mess, use an anal douche prior to your dildo-to-ass play. Actually the douche is quite pleasurable in itself, a little ass foreplay if you will, so it isn’t a waste of time at all.

Butt Plugs

I use to laugh at these thinking they were some kind of fem-dom thing. That is until I tried and now absolutely love them.

These usually come in a set of three or so of graduating widths. The object is to start with the most narrow width and work your way up to the largest width. While the butt plug isn’t exactly for masturbation, per say, their use can’t be any simpler. Just put on a bit of lube, insert just past the sphincter and go about your day, even in public.

The pleasure comes from just your everyday movements. For example, sitting down or bending over stimulates the prostate leaving you with a light tingly feeling. As well, movements in your hips can also trigger feel-good moments. You won’t always realize that it is there, yet it is those moments that you do when it becomes pure joy to have on.

For maximum effect, wear pantyhose underneath your jeans or pants. The silky feeling on your legs combined with the pleasuring butt plug is a combination made in heaven. The best part is you can pass by everyone at the office and no one will even have a clue.

The Mermaid

I’ve seen pantyhose worn a million ways but one in particular actually is quite erotic for yours truly. Also demonstrated in the image above.

So while in your pantyhose (important), take another pair and put both your nyloned legs through just one of its legs. Then pull it all the way up to the bottom of your butt. With the other unused leg, tie that tightly around the bottom of your butt securing it into place. Don’t worry, this won’t ruin the pantyhose so try it with a high quality pair (e.g. Wolford Neon 40 highly recommended). The more smooth and silky, the better.

What you have now are your legs feeling somewhat bound, as if it were rope, but more so a feeling of completely trapped in silk. After squirming around trying to “free yourselfย ” you’ll notice the all around sexy feel of your legs tightly pressed and rubbing together along with the silky outer covering keeping them in place. Basically, if you’ve never tried this, do so because the silky tight feeling is irresistible.

This also works infinitely better when combined with one of the other two toys from above (like I did just after snapping the pic).

* * *

Hopefully you’ll enjoy one of these but if you have another technique, don’t be afraid to let me know below ๐Ÿ˜‰

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Posted in Erotic Thoughts
30 comments on “More Kinky Masturbation Ideas, So Things Don’t Get Boring
  1. Gezza says:

    this is my kinky masturbation fantasy:
    what I’ll be wearing:
    auburn face framed wig
    white lacy all in one bodysuit
    tartan micro skirt (9 inches)
    white hold ups
    heels
    Set digital camera up in position (video mode)
    stick a slinky pink suction cup dildo (7 ot 8 inch) to the wall and set camera recording. Double check it’s the best angle/lighting/full view shot.
    Playfully stroke dildo with hands, applying flavoured lube, (pretend to masturbate the cock)
    sink to knees, with back slightly to camera so skirt rides up to show off some bottom cheek, give the dildo a blowjob, slowly and deeply with lots of “sighing” noises. Put hand up skirt and rub your pretend female heaven.
    stand up, and rub cock between your legs, pretend it’s trying to enter you like a woman. apply more lube and turn to face away from dildo, ease aside the lacy lingerie and allow oneself to gently slide onto dildo and gently fuck the cock, rubbing yourself under your skirt until you cum in your lacy lingerie….
    lie back in the afterglow and watch yourself again on the camera.
    My other fantasy is to drive around in the countryside dressed as a girl, set up camera again in remote spot, and stick dildo to car bonnet and enjoy sex al fresco – in a safe secretive place of course.

  2. Sheery says:

    I’ll take the first one, thank you. Thanks for sharing Gezza and send me the video when done ๐Ÿ˜‰

  3. Pantyhose n' Poppers Queen says:

    Hi Sheery!

    Great review!

    As mentioned in a previous post, my personal favourite anal toy is the Aneros Syn Silicone prostrate massager. They are very expensive for what they are but the way they intensify an orgasm is awesome, plus they can be worn under pantyhose as the fit is very snug…I’ve also managed to have prostrate orgasms too which are fantastic!

    Absolutely right about doing an anal douche first, though sometimes I am just too lazy and do indeed end up with cookie dough on it afterwards. One time I was in bed with my wife and I’d put a butt plug in, just as we started to have sex the bloody thing shot out of my ass and there was a quite a dollop of cookie dough on it. Fortunately, she saw the funny side of it but it did rather kill the mood….:-((

    As for the Mermaid, have you ever heard of a body cocoon? It’s a 30 denier sheer body-sized stocking which is sealed at one end, you can get inside it fully and even bring it over your head, very erotic when you wear a pair of pantyhose too..:-))

    Link

    http://tights-for-men.com/index.php?main_page=product_info&products_id=110

    Thanks for your great website!

    Xx xx xxx

  4. Sheery says:

    Yes anal play is fun fun fun but you do have to keep it clean down there.

    I’ve seen the body cocoon online but never knew where you could get it so many thanks for the tip. Looks quite fun to use actually!

    Thanks for your comment PnP Queen.

  5. T says:

    Thank you so much for your post!It’s so refreshing to read about others who experience the same feelings and same lifestyle out there! Love it!

  6. Sheery says:

    That’s what I’m hoping for. Thank you for your kind words T. X

  7. Janice says:

    The mermaid is a particular favourite of mine. I love full body encasement too. That combined with a vibrator, as suggested, really does make the time fly by!

    Janice x

  8. Sheery says:

    Next time try them in your Wolfords ๐Ÿ˜‰

  9. Janice says:

    Wow, fully body encasement in Wolford Neon 40s is the stuff of dreams Sheery! No. 1 on the To Do List ๐Ÿ˜‰

  10. Lisa T says:

    Here is a fun little kinky thing you may want to try. One night on a whim I jumped into the shower with my pantyhose on. I was totally amazed at how fantastic my pantyhose felt soaking wet! They had an incredible cling as they totally molded themselves to my lower body. Taking my shower massage and directing it right on my crotch was all I needed to put me over the top. Since then I’ve showered and taken baths in my pantyhose often and never fail to enjoy it. Of course there are other, kinkier, variations which I will be happy to tell about if anyone is interested.
    Lisa

  11. Sheery says:

    Actually I like pantyhose in the shower too. The thick dancer tights are a little more fun when wet I think ๐Ÿ˜‰

  12. silkytights says:

    Oh lisa t please tell us more about your kinkier variations. I also wear my tights (pantyhose) in the shower it is really erotic. X

  13. Silksatin38 says:

    I tryed the mermaid as discribed above with some gypsy satin sheen pantyhose,but to make it even more amazing i wore a full slinky satin slip over the pantyhose, OMG!! i was in absolute heaven gave me best orgasm i have ever had exploded within in minutes without even touching my penis just slided the satin up and down the silky pantyhose whilst wriggling in them.Will try it with a butt plug next time around wow. X

  14. Sheery says:

    @Silksatin38 (high five)

  15. cari says:

    This is a fun one as like many of you love to jack-off while crossdressed or just wearing pantyhose.

    I learned this from a woman actually who has a pantyhose fetish herself. She would blow a guy and save the cum in a little cup and freeze it. So the next time she would masturbate, she would take the cup with cum and pot it in here mouth. When I first tried it, it was with my own cum. I saved up about 5 loads so I had plenty.

    First, get dolled up or put on your pantyhose up to several pairs at once. And fantasize about what most turns you on being getting laid, giving head or whatever it is.

    Then go to your freezer and get the cup of frozen cum and put it in your mouth. ( It melts pretty fast ). Lube up your ass with is ( I cut a hole in my pantyhose for dildo and butt-plug use. )

    Then put some of the melted cum on the dildo, finder, butt-plug etc. Meanwhile enjoy the cum that is still in your mouth. ( If you enjoy water-sport ) piss into a cup. Stand in the shower or lay in your bathtub. Pour the piss on you and get your pantyhose covered with the piss. Meanwhile keep swirling the cum in your mouth. Slide the dildo or butt-plug in your ass. Let your sexual imagination run wild.

    Drip some cum onto your cock ( awesome lube ). and one of two things can happen, your pantyhosed cock might cum without even touching it or start jacking off the way you know you enjoy it best.

    Have fun with it. ๐Ÿ™‚

  16. Cindy says:

    I have gone out all dressed up met someone who just rubbed my panties till I came. Most amazing orgasm I’ve ever had felt.. No toys or stroking needed. Felt so much like a woman in my wet panties

  17. Nylon Fet says:

    Here’s how I masturbate in pantyhose. I put on two pairs, the first pair has a hole cut out for my penis which has a nylon stretched tightly over it. I then put on my favorite vintage double nightgown which helps add to the silky slip and slide friction. Pull a nylon over my head, put on a ball gag, and hog tie myself in self bondage. The friction of my nylon covered penis encased by the second pair of pantyhose drives me to organsm as I struggle against the bonds.

  18. Darling2 says:

    Yes it’s fun to read the different masturbation, some are similar to other…depending what excits one another. As for me, i also wear two pairs, most of the time I would say, some have holes (in the gusset area) for my penis in case I feel like strocking my cock. The first pair usually skin coloured and the second black, coffee, purple, etc and finally a nice and sexy bodysuit on top…if reall y feel horny…and i masturbate the hole day. I play with diffent accessories I wait the ultimate moment for ejaculation…;) mmm sooo good.

  19. ronco jones says:

    I must say I have a pleasant african life. Im european birth but black chicks make me hot instantly. After an enjoyable phase I have found my wife give me the usual sex life which is boring to me…I feel I need more sexy stuff in my life right now,…so…Im happy to meet you. Please let me know what are your thoughts, preferably black women who I can make squirt online…or not…;)

  20. Kim says:

    Life is so short, enjoy your sensuousness. Lingerie and high heels look sexy! Wear them! The only problem might be that you look better than your girlfriend. She could resent that. But if she loves you, chances are she will not only let you bht will assist you in achieving the feminine look you desire.

  21. Kim says:

    I wear very expensive pantyhose. I prefer not to get them too gooey with persperation or cum. At 50.00 per pair, I wear them to look nice, not to get runs or have to launder them excessively.

  22. Sheery says:

    @Kim I know what you mean… I almost never wear my expensive pantyhose. A shame!

  23. Kim Cummings says:

    I spend a extrordinary amount of money on my Wolford’s pantyhose. I usually don’t bother to launder them. I usually just replace them. I know that it’s really expensive but they will get snagged before they get to soiled. Snags are going to happen. As careful as one is. Gloves and pedicures and lotions help.

  24. Sheery says:

    @Kim I don’t know what is more fun… wearing Wolford pantyhose or buying them at the botique.

  25. Kevin...also known as "Cynthia" says:

    Strange how my comments never seem to post here, but…here we go again…
    I am a big fan, Sheery. When I first saw your Confessions in Pantyhose site, I felt like I had finally seen a kindred spirit.
    My favorite thing to do while wearing pantyhose is sucking myself off.
    Been able to do it since I was a teenager and I used to suck myself and wear my sheer-to-waist black pantyhose for hours.
    When I was in high school, I got almost nothing else done but slurping away on my meat and wearing pantyhose. =)

  26. Sheery says:

    @Cynthia Thank you… of course us CDs are kindred spirits!

    You must be very flexible as well. I take it you never have to leave the house.

  27. Kim Cummings says:

    I’m not a contortionist. I am flexible, but not that flexible. I prefer a nice quality vibrator with multi -speed. The pantyhose and panties including any other slips, lingerie, and even a small device inserted into your “pussy” is really good and can be used for the pleasuring of a “naughty” Mommy and her family and friends. We have a nice little fetish for her wet panties and pantyhose together with high heels! Come tell Mama what you think of our lovely experience with this new forbidden taboo relationship.

  28. Kim Cummings says:

    As a Mother myself, and alone, I have been a naughty mommy and I will confess that I have been wearing my pretty sexy lingerie and high heels around the house. I have a daughter and a son that is drawn to the new feminine looking “daughter” Mommy needs her sweet “girl” to be. The feminized “girl” is quite a bit in touch with our feminine ways. The introduction to this transformation of my own “daughter” was just a few stimulating items of interest in the world of the sensuous feeling of our own hot and sexy fetishes and the other ways of the sensuous persuasive nature of our own families requirements. I didn’t have to do anything to get “her” to immediately understand that this was necessary and eventually the only way to go. “Oh, yes, Mommy, it is so right.” I always wanted this and the spirit of sanctity we share in this case is so important to us.” I’m ready for us again to be as one”! We were all very excited to announce the love and care for each other and the impending years of experience in the world of incestuous intimate and carefully indoctrination we were all very excited about. The mother and her “daughter were involved in this requirement of the hot and sexy knowledge of this kinky sexual world. The mother was obviously using the fetishes the hot “daughter” intensity of the sensuous feeling of the smooth and satiny pantyhose together against each other’s pretty legs had on the seductive Mommy and her “sissy ” daughter’s clit. Her legs opened up as the mother’s demand for the daughter was insisted upon the itinerary of the incestuous transvestite group of the hot “daughter”. Her mother and her naughty little girly bitch started to embrace the once again that special feeling that the two of them knew so well. Mom’s cunt was soaking as the lust and the smooth pantyhose against her “daughter” made it clear to the mother that the cock -Clitty through the pantyhose was working in the mother’s cunt deeply. The incestuous transvestite delved deeply into the wet and ready cunny as the lust and the Mommy’s lonely desire for the hard cock in her pussy through the pantyhose struck home. “Good girl, now reach out and stroke my pantyhose as I caress your pretty legs”! “Mommy, are you sure that I am doing it right”? The brazen woman told the truth as she encouraged the hot “daughter” to slowly and sensuously drive her Cock in her pussy through the pantyhose! She squealed as did the bitch screaming at the mother to tell the hot bitch how much she loves to Fuck her “daughter ” The mother started to get involved in a frenzy of the most encouraging language that the “daughter’s” never heard before. It was a heated incestuous detailed description of what the mother would know would have the desired effect on the powerless and now unafraid lust driven “bitch” was seeking . “Mommy, you are so hot looking and you are making me feel like a good girl for you “! The mom knew that the girl who was a little more than ready for the next step in the mother’s demand for the daughter to be involved in this situation of a new experience in this situation of the incestuous lust and how much that it would be better to be a naughty mommy and tell her that she had to do” certain things ” to the mother.

  29. Kim Cummings says:

    My mom was adamant about her little girly Boi earlier in my life. Mama’s Gurl was a little bit of a naughty girl for the Mother. She had a explicitly detailed description of what I was to be dressed in. It was mandatory for me to let mother pick out the most feminine outfits for her sweet and loving now feminized girl. She was thrilled with the new intimate apparel and high heels she provided for her new sweetie. I bought a few items with mommy at the lingerie boutique. The sales girl was helpful in getting a new look for her customer. We went into the dressing room and she said :” Let me suck you off just like your mommy does”! I squealed as the girl sucked my cock through my silky-smooth pantyhose. “Mom watched as well. I soon was inside Mama’s pussy. The sales girl also took care of mommy. Mommy said:” Let us know if you want to be a good little Bitch for your customers. The girl nodded and approved of the sensuous idea. I fucked both of them. They were usually always wearing pantyhose and high heels. I was also wearing my pantyhose and high heels. “Put it in my pussy slowly and carefully. ” I smoothly and carefully sliding in her pussy through our pantyhose gave the hot women all the pleasuring they were entitled to.

  30. Kim Cummings says:

    Working at a woman’s shoe store I was able to make the most of the experience. The dresses were short. Often the girls wore nylons or pantyhose. I often suggested that we had a great sale on high heels and nylons. The girls were giggling. ” I think I have your size in these new open toe 4 inch high heels ” I would bring out the high heels and the smooth feeling of the girls legs as I slipped the high heels on their feet was so much fun. The girls usually couldn’t make up their minds. So I offered to discount prices on them. I sometimes even got a phone number.

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