Anal sex includes the insertion of both toys and real cocks into the sissy’s ass. Buttplugs can be used as part of sissy bondage as well as preparation for the sissy to be ass fucked by either strap-on dildo or a real penis. Anal probes can be pumped in and out of a sissy’s butt. A wife or mistress can fuck the sissy up the ass with a wide variety of strap-ons. Some strap-ons come as prepared units, with built in belt or panty and built-in dildo, often with vibrations and some kind of stimulation for the woman. The ultimate in sissification is having the sissy take it up the ass from a real man, especially while in bondage as part of cuckolding.
Anal play can include analingus (ass licking), butt plugs, anal probes, anal beads, strap-on dildoes, and anal copulation.
Please learn more about bondage safety before actually engaging in bondage.
Anal kits combine multiple anal toys into a convenient package and are a good way for beginners to start experiencing anal toys.
Anal probes and butt plugs are designed for use in the anus. These come in a wide variety of shapes, colors, and materials, as well as with and without vibrators.
Anal probes are toys that are inserted into the anus. Some are vibrators, while others are sleeves or attachments that go onto an already existing vibrator.
The sissy gang-bang challenge is both a fantasy and a potential reality. The real-life version should involve the use of condoms for safety. Nobody should be forced against his or her will to participate in a sissy gang-bang challenge. The fantasy version is often more extreme than a real version.
picture courtesy of femminilizzazioneforzata
There are far more sissies who want to serve a genuine girl mistress than there are potential biological female mistresses who want and can support a personal sissy.
In a sissy gang-bang challenge, two or more sissies bidding to serve a particular mistress spend one to four hours being gang-banged. The mistress sets the rules and scoring and has final approval of the sissies allowed to compete in the sissy gang-baang challenge and final determination of the winner(s). The mistress may at her sole option dismiss an existing sissy as a result of a sissy gang-bang challenge.
The costumes worn by the sissies may be identical, similar, or different. In some cases the skill and creativity at dressing is part of the competition and points may be awarded for best costume, best makeup, and other categories. Points may be deducted for imperfections in costume, make-up, demeanor, and other categories.
Some common costume choices include: sissy maid, adult baby, belly dancer, cheerleader, nurse, pony girl, school girl, secretary, stripper, or whore.
The participating sissies are almost always in severe bondage, in any position that allows easy access to both the sissy’s (sissy pussy) ass hole and the sissy’s mouth hole. Panties may be pulled down or have access holes. Usually two sissies are placed in identical bondage. Usually grousp of sissies are placed in different bondage positions, especially if the respective masters and/or mistresses of the participating sissies want to show off their skill and creativity.
Bondage furniture may include: post bondage and bondage horse.
Participating sisies may be positioned so that their sissy cocks (or sissy clits) are inside the hole of a doll (normally a latex or strong vinyl inflatable doll, but a foam or silicone doll for wealthier players). Sissies may be penalized for any unauthorized ejaculations. Sissies may be penalized for failure to ejaculate on command. Penalties may take the form of loss of points, physical punishment (whippings, spankings, etc.), or both.
Participating sissies may be paddled, spanked, whipped, etc. as part of the sissy gang-bang challenge, usually as the beginning of the sissy gang bang challenge. Not all sissies like or are willing to participate in ass beatings. Sissies vary in how strong an ass beating is acceptable. Real-life versions should respect limits. Fantasy versions have no limits.
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The central activity of the sissy gangbang challenge is the gang bang.
Often participating sissies will get points for the number of times that a macho man cums in the sissy’s ass. Usually ass fucking that doesn’t result in the macho man cumming does not count for points. Macho men may freely tease and torment the sissies with extra ass fuck strokes that don’t count for points. Macho men are free to switch to any available hole on any participating sissy at any time, including in order to cum. Macho men are often free to pull out and cum on the sissy’s body and/or costume. Some mistresses or sissies do not want particular costumes and/or wigs and/or shoes ruined. Normally pulling out does not count for points.
Macho men may normally jerk off and cum on any sissy’s body and/or costume at any time. Some mistresses or sissies do not want particular costumes and/or wigs and/or shoes ruined.
Often participating sissies will get points for the number of times that a macho man cums in the sissy’s mouth. Usually blow jobs that don’t result in the macho man cumming don’t count for points. Macho men may freely tease and torment the sissies with extra mouth fuck strokes that don’t count for points. Macho men are free to switch to any available hole on any participating sissy at any time, including in order to cum. Macho men are often free to pull out and cum on the sissy’s body and/or costume. Some mistresses or sissies do not want particular costumes and/or wigs and/or shoes ruined. Normally pulling out does not count for points. Sometimes deep throat earns the participating sissy with additional points (sometimes fractional points).
Often participating sissies will get points for the number of times that a genetic woman cums while using a strap-on to fuck either the sissy’s mouth or ass. Usually any strap-on use that doesn’t result in the genetic woman cumming don’t count for points. Real women may freely tease and torment the sissies with extra mouth and/or ass fuck strokes that don’t count for points. Genetic women are free to switch to any available hole on any participating sissy at any time, including in order to orgasm. Genetic women are often free to pull out and stop at any time. Sometimes deep throat earns the participating sissy with additional points (sometimes fractional points). Sometimes a woman may grant bonus points for better quality experiences. Sometimes a woman may deduct points for lower quality experiences.
Often participating sissies will get points for the number of times that a genetic woman cums in the sissy’s mouth. Usually any cunnilingus that doesn’t result in the genetic woman cumming doesn’t count for points. Real women may freely tease and torment the sissies with extra cunnilingus that doesn’t count for points. Genetic women are free to switch to any available sissy at any time, including in order to orgasm. Genetic women are often free to pull away and stop at any time.. Sometimes a woman may grant bonus points for better quality experiences. Sometimes a woman may deduct points for lower quality experiences.
The most common pattern is for the participating sissies to all be furiously double fucked by different combinations of men and women, followed by a slowing of frequency and ellapsed time of fucking. It is in this later part of the sissy gang bang challenge that the superior sissy typically starts to get more and more of the points.
Sometimes the winner is determined by which participating sissy is chosen for the last strap-on fuck or cunnilingus of the sissy gangbang challenge. Sometimes the mistress will orchestrate a final double fuck and then announce the winner of the sissy gang-bang challenge. Sometimes a mistress will delay the announcing of the winner of the sissy gang bang challenge.
At the mistress’s option, the winner may be added as an additional personal sissy. At the mistress’s option the winner of the sissy gangbang challenge may replace the (or an) existing personal sissy. At the mistress’s option, the winner may be turned down for the position of personal sissy. Any existing personal sissies may be kept or dropped at the option of the mistress.
picture courtesy of femminilizzazioneforzata
Being fucked like a girl (“womaned”) and filled to brimming with fresh semen from a real cock is perhaps the most feminine of experiences any sissy will ever experience. It’s also one of those things where practice makes perfect, so to say. The best thing a sissy can do for herself prior to any anal sex experience is to train herself for it with progressively thicker vibrators and dildoes; and to get used to douching (no explanation needed) and using feminine lubricants and vaginal cremes. Proper feminine hygiene (including the wearing of a feminine napkin afterwards), besides being common-sense mandatory, also will serve to further emasculate any sissy. Then when the magic moment finally comes (when he slips it inside) … it won’’t hurt and will slide in and piston easily in and out, in and out, in and out … Ooooo! And there is absolutely no greater feeling of femininity than to feel that stiff male sausage and then that spritz and splash of semen going up inside—and then afterwards. . . sensing the creamy sperm inside as a sissy continues her day in her panties. It gives the sissy a sense of “belonging”—sort of a message to her that she “belongs” in panties and skirts, so to say, and a justification as to why she wears skirts or was put into them in the first place. ’Sissy Nancy; e-mail
“The way I break in a new pair of CFM heels is to get laid in them.”—hi-heeled tv; e-mail
“I love my ass played with! Been fucked once. So good!”—bi-tex; e-mail
“Never been fucked by a real dick, just a nice big dildo that I take balls deep. Drives me insane.”—tv in midwest; e-mail
“You want to be my bitch don’lt you, you like pleasing your mistress don’t you…taking it up the ass & sucking off all the neighborhood men, especially Big, Black John, bet you love having a BIG, BLACK COCK up your ass!!, while you are dressed in those little black lace panties & bra. I WILL spread your ass cheeks wide & ram this thick strap-on cock up your assholemaking you scream with pleasure!!!
“Come on you little sissy bitch, I know you can take this whole cock.
“I love watching you while you get fucked deep up the ass & seeing your mouth wrapped around a nice hard cock, especially while your derssed in those little black panties & bra, I WILL spread your cheeks NICE & WIDE while I make you my sissy whore!!!
“Cum on & bend over, spread them ass cheeks for me!”—Strap-On-Vixen; e-mail
Share anal sex suggestions at contact00@RealSissySchool.com
picture courtesy of femminilizzazioneforzata
Men’s Open Rear Lycra Bikini Pouch Lingerie Sissy Pantie Cross Dresser Man Panty
Brazilian Butt cut. A cheekier look. Regular lace is now used in these panties. UNLESS picot elastic is requested.
available at ebay sold by jlizzyapparelandlingerie
Another idea that is good for any sissy is to have her sew her own little lace trimmed access hole in the back of some of her panties. The hole can be heart shaped, elliptical, or round. Lace trim is a nice little touch. Besides being a good project for any sissy (sewing her own panties), the access hole can also become very practical whenever her man may desire a “quicky” by simply bending her over, raising her skirts and petticoats and slipping her the quick cock from behind—“taking her from behind” as it is known.
One other humiliating experience that is good for any sissy, concerning her “access” panties is when, for instance, she is changing her dress and petticoat in front of other women … when they notice the “curious little hole in back” and start quizzing the sissy what the little lace trimmed hole is for. Then to hear them figure it out for themselves and start giggling with glee and cooing and clucking with approval.
e-mail from Sissy Nancy; 18 January 2005
zip-access botttom
Crossdressing, feminization and bondage are my passions. Femdom and humiliation are the spices... :-)
Alex
picture courtesy of femminilizzazioneforzata
Copyright © 2004, 2005, 2006, 2020 RealSissySchool.com
Last Updated: May 12, 2020
Created: June 13, 2004
Based on material previously at AdultToyReviews.com
Author of this sissy lesson page: contact00@RealSissySchool.com
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