Crossdresser Asshole
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Crossdresser Asshole
What’s the nastiest cross-dressing experience you ever had?
Former Retired Peace Officer and Husband · Author has 155 answers and 105K answer views · Jul 23 ·
Did crossdressing ever lead you to any gay acts or vice versa?
What has been your proudest crossdressing experiences ever?
Have you ever been forced to crossdress by your wife/girlfriend and shown off to her friends?
Has a woman ever approached you while you cross-dressed, and what happened?
Masters Degree in Chemistry and Biology , University of Massachusetts System ( Graduated 1982 ) · Author has 696 answers and 1.4M answer views · 2 y ·
Did crossdressing ever lead you to any gay acts or vice versa?
What has been your proudest crossdressing experiences ever?
Have you ever been forced to crossdress by your wife/girlfriend and shown off to her friends?
Has a woman ever approached you while you cross-dressed, and what happened?
What has been your best crossdressing experience?
What was the worst or most embarrassing experience for you as a crossdresser?
Have you ever cross-dressed with another male?
As a crossdresser, has a guy ever hit on you while you were out dressed up?
As a cross-dressing man, did your son ever hit on you?
How many people have you told about your cross-dressing?
As a cross-dressing man, have you ever been caught and punished by a woman for wearing her clothes?
When was the very first time you cross-dressed, and did you like it?
Have you ever bummed a crossdresser, how was it?
Have you ever caught someone else crossdressing?
Did crossdressing ever lead you to any gay acts or vice versa?
What has been your proudest crossdressing experiences ever?
Have you ever been forced to crossdress by your wife/girlfriend and shown off to her friends?
Has a woman ever approached you while you cross-dressed, and what happened?
What has been your best crossdressing experience?
What was the worst or most embarrassing experience for you as a crossdresser?
Have you ever cross-dressed with another male?
As a crossdresser, has a guy ever hit on you while you were out dressed up?
As a cross-dressing man, did your son ever hit on you?
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Sandy’s Hubby again. As stated supra., I was forced into my female partner’s clothes by gang bangers 40 years ago. Horrible at first, Nasty for three days. Things I seduced and coerced women into doing sexually in the past, came back to haunt me. I have gynecomastia, and I was even tit fucked. My female partner enjoyed seeing me debased. Giving head and being screwed at the same time while in a dress flipped over my back, with panties rolled down in back but not in front, made me feel like a woman. Anytime I ejaculated in the panties, they were stuffed into my mouth. I also had to lick my fema
Sandy’s Hubby again. As stated supra., I was forced into my female partner’s clothes by gang bangers 40 years ago. Horrible at first, Nasty for three days. Things I seduced and coerced women into doing sexually in the past, came back to haunt me. I have gynecomastia, and I was even tit fucked. My female partner enjoyed seeing me debased. Giving head and being screwed at the same time while in a dress flipped over my back, with panties rolled down in back but not in front, made me feel like a woman. Anytime I ejaculated in the panties, they were stuffed into my mouth. I also had to lick my female partner clean after she was screwed by them. She is now my wife of many years. We still recall, and fantasize about those three NASTY days! Any time we want to relive them, we role play and keep it filthy, kinky and Monogamous. I cross dress sometimes and she pegs me. Other times we play as two Lesbians.
Nasty in what way? Once when I was crossdressing and the woman I was with requested that I wear a skirt with thigh highs and no panties. We were walking on the sidewalk one evening at twilight and she lifted the front of my skirt and tucked it into the waist band and would not let me pull it down. So I was now exposing my fleshly shaved clitty to anyone that happened to walk by us or look out the windows of the shops we passed. I told her that I would not enjoy getting arrested and she just laughed at me. Occasionally she would reach over and stroke me and try to make me hard. I eventually sta
Nasty in what way? Once when I was crossdressing and the woman I was with requested that I wear a skirt with thigh highs and no panties. We were walking on the sidewalk one evening at twilight and she lifted the front of my skirt and tucked it into the waist band and would not let me pull it down. So I was now exposing my fleshly shaved clitty to anyone that happened to walk by us or look out the windows of the shops we passed. I told her that I would not enjoy getting arrested and she just laughed at me. Occasionally she would reach over and stroke me and try to make me hard. I eventually started to get hard and I just in time pulled down my skirt before encountering a mother and her kids. Fortunately, for me I looked feminine enough so that the mom and her kids thought that we were just to girls out for the night. This was very exciting but very scary at the same time.
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im having first date as a woman, i need to know is there something i can use to ease the pain of first anal intercorse
7:24AM, 20 May 2011 PDT
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Try using a dildo for a few days prior to you date so, you stretch yourself. Then have her enter you slowly until all the way in. Once all the way in she can pound away 'till she cums. You'll love the feeling of her exploding inside you and filling you up with hot cum. Good luck.
ages ago
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Have your male lover lick your asshole for a while and then tongue fuck you deep. He'll be lubricating you and then he'll insert a finger, then two, stretching you butthole for his cock. Spread your asshole with both hands and make sure he uses a lot of lube. You'll feel his head push past your anal opening and he'll give you deep thrusts, making you his whore. I would finish missionary, that way he slams his balls against your sissy ass cheeks and you can squeeze your hole making it real tight for his cock. You'll want him to cum in your ass and then lick his cock clean like a good bitch.
ages ago
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Babes, I dont wish to sound like Im putting you off, but in general what gurls describe as their first time anal experience is often not what it really is.
As Lilly says ideally you need to get your "pussy" accustomed to anything going in, your pussy is built to let things out. It does get better through practice and experience, but dont think that on your first try, you will be fully pentrated and enjoy it, all takes time, but what I can assure you of that when your pussy becomes accustomed to being entered then it is a fab feeling.....
Take Care
Lucy
xxxx
ages ago
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It's definitely good to play with dildos, smaller butt plugs etc. before your first penetration to stretch your pussy a bit. But my first time was wonderful. Make sure his cock is not too big. Doggy style is a great first position. Make sure you're well-lubed. When he starts to slowly penetrate, relax you muscles and push back against his cock gently. Then squeeze and relax your muscles, and he should slowly go right in. Once in you, he can pump your pussy faster and faster until you both cum.
ages ago
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tell us. how did your date go thanks
ages ago
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I am glad someone asked this Question. I hope to need the advise soon Myself.
ages ago
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Beth's advice is right on.
ages ago
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First time I had anal sex I was a bit durnk (very drunk?) All I can recall is that it was great. I screamed because it was painful. I screamed because it felt so good.
Do not be afraid to tell him it is your first time. The best sex I ever had was with a man who knew he had to prepare my ass for his big cock. He spent the better part of an hour getting me fully ready using both his fingers and his cock. And when he gave it to me it was still painful as he was so big and when so deep. INCREDIBLE!!!!! (If only it could always be so good.)
Oddly enough check out youtube with keywords 'anal sex/' there are some great videos on positions and lubrications etc.
Veronica
ages ago
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JaymiCDSweety,
You are an Very Sexy Rocker Chic, Good Luck on your Quest for First Time Anal, I hope you suceed
Rose
ages ago
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I had been using toys, plugs for some time loving the feel and the way I felt inside
but still needing to know if it was a part of my life missing that I needed then the first time meeting him and deciding this would be the night, nervous scared, knowing how this would be life changing for me a doorway that would lead me on a different path and one of no return giving me a label by society that I would have for the rest of my life.
When the moment became reality it was wonderful giving me more of a complete life emotionally and sexually
95 months ago
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At 14, though not ready to make my debut on the street, I was discovered by one of my teachers wearing a bra and panties. "Not to worry", he said and then began getting very friendly with me.
One day he invited me to his flat to take some pictures of me dressed. I arrived completely underdressed and took only a short while to finish, do my hair and put on some makeup. He was surprised I could walk so well in heels and was very impressed with the femme me.
He shot a roll of film with me in some ho-hum poses and then asked to see some leg and then to open my blouse. This was followed with some lingerie shots, for which he provided some of he lingerie. As normally happened I got a hard-on and he said we'd have to "do something about that". Soon his hand was under my slip and he was grasping my cock in his hand. It felt good and I told him so. This prompted him to take out his cock and without a word push it into my mouth.
He held off cumming and had me remove my panties and rolled me over on my stomach and in what seemed like two seconds I felt his cock pushing itself inside of me. It hurt but I knew it had to happen sooner or later and so I just accepted it. He was well lubed and once his length was all in me and his stroking became more rhythmic the pain wasn't so bad. Soon he was cumming and though I felt no physical satisfaction, knowing I had satisfied a man like that made me feel more like a girl than I could describe. After cumming he stayed in me and when he was somewhat soft he removed himself and began kissing me. While I was laying there he took me into his mouth and gave me what he said I "definitely deserved". And it was good.
In school the following Monday he was very cordial and said he'd have the pictures in a couple of days. And he did give them to me including the negatives. They were simply a ruse to get me to his flat for the seduction, which was to be one of many.
When I began going out dressed he was my escort a few times, once referring to me as his "daughter" and another time as his "niece". He was in his late 40s and I loved it. We went to movies and for walks; took the Staten Island Ferry and even went to a couple of Broadway matinees.
Our affair continued until I graduated which coincided with his getting a new job requiring a move away.
During our time together there were others, men and boys, and it soon became quite pleasurable, as it remains today, in my autumn years.
61 months ago
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To ease the pain of anal intercourse use any product with Lidocaine.
61 months ago
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ricki4678 :
Oh God, yes! Lidocaine mixed with vasoline.
61 months ago
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the first time i had anal sex was just a week ago. i started playing with a small toy and after a while, i could not cum hands free, however, i played again with a bigger toy a few days later and was able to orgasm hands free. it felt incredible and honestly i have never cum so much or hard before
60 months ago
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if you a complete anal virgin, i wouldnt even recommend starting with dildos - so far as i am concerned, the best way to prep to receive is to start with a finger. Make sure nails are smooth and not too long ... or use surgical gloves.
When it starts to feel uncomfortable, stop and do same again next day.
When you comfortable with a finger, progress to two.
Then you you have become accustomed to insertion you can move on to dildos.
You can of course dive straight in - but it probably will hurt
60 months ago
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i had been fingering myself before i tried the small toy and enjoyed it, but wanted to feel something bigger inside of me. fingers do help, but soon you will outgrow them
60 months ago
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I did not prepare I wanted to feel like a virgin and have the pain turn i8nto pleasure
38 months ago
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new to the site
never had it
38 months ago
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Still waiting for my first time
37 months ago
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Relax use lube insert a little at a time then once your feeling comfortable sit back and enjoy the ride after its all over you will be saying DO IT AGAIN
37 months ago
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Never but think I want to
37 months ago
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Thanx for advice xdresserrandi
37 months ago
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first time hurts but well worth it
37 months ago
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I so looking forward to having my cherry popped.
37 months ago
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My wife introduced me to anal sex. She was slow, patient, used plenty of lube and didn't push me more than I was comfortable. She made sure that she pushed all of the right buttons so it was very pleasurable for me. With-in a m
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