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age
41-50,
anonymous
writes: I am a male and take on the role of the woman in my relationships with other men. I am a crossdresser and dress like a woman and love wearing lingerie. I give blowjobs and want to recieve anal. I have not yet but my bf wants to do me anally . Any advice on what to do to make it a great experience and to make him happy. Also should i wear black or white lingerie to impress and any suggestions on sexy attire.
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male
reader, anonymous, writes (4 June 2009): yes wear black for him .and tell him that you want spanking first .that will take the sting out of your bottom when he enters you from behind
A
reader, anonymous, writes (26 May 2009): This is verified as being by the original poster of the questioni went out and bought some red lingerie and i am going to wear it for my boyfriend tonight . wish me luck and tonight is going to be the night i lose my virginity by recieving anal from my bf tonight . this will be my first experience in recieving anal i am so excited i cant stand it. thanks again for the good advice that you all gave to me.
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reader, anonymous, writes (26 May 2009): This is verified as being by the original poster of the questionArmy wife this is a real question.And yes i am serious. I have been a crossdresser since i was really little and have always felt like a woman trapped in a mans body. Up until 1 year ago i was married to a female and we divorced because she did not like my crossdressing and plus she caught me giving her brother a blowjob. i have given blowjobs alot and never recieved anal because i wasn't reaDY. I give blowjobs, not recieve them , i want to recieve anal not give it because i view myself as a woman. one day when i get the money i plan on have the sex change operation to become a woman.
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A
male
reader, anonymous, writes (26 May 2009): im a 15 yr old male and i am what you call "bottom gay" when i first started with my bf i let im LUBE his fingers, and insert 1, then 2, etc until 4 close together which is about his girth.
after he finished fingering he didnt let my hole close b4 he inseted himself, which makes it so there is no 'pop'. have fun but take it nice and slow the first couple of times
the reason LUBE is in caps is its the most imporant thing. use proper lube specialy designed for anal. i.e. gun oil, ky, or easyglide.
p.s. if you bleed dont worry unless its an alarming amount, or if it is bright red, with nothing mixed in. in that case go to the nearest A&E/ER immediatly. i know it will be embarrasing but you gotta if youve done damage
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A
female
reader, Karlin24  +, writes (26 May 2009):
 And by he way, color of lingerie? RED!!!!
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A
female
reader, Karlin24 +, writes (26 May 2009):
Well "Girlfriend", as a woman that enjoys anal on occasion, I can give you tips from my experience. After all, an ass is an ass whether it's male or female. I learned all my best anal sex tips from my ex-boyfriend who had to have some type of anal stimulation everytime we had sex. Not sure if he really wanted to be with a woman, which could explain why he's my ex.
These are tips based on my experience and may not be best for you, but it works for me.
First, I usually have a couple drinks. Not to the point of drunk, but just enough to let my inhibitions down a little and relax.
Second. I want to be clean. You know, freshly showered and empty my bowels if possible.
Third. You should be incredibly turned on to do this. Anal licking is extremely erotic, as the anus has alot more nerve endings than other parts of your body (which elaborates on the "clean" point. No one wants to lick a "not so fresh" anus).
Fourth. Lube, Lube, and, oh yeah, more lube! Enough said about that.
Fifth. Talk to your partner about "slow and easy" which is the two main words he needs to remember if you're going to do this. Any other way can cause damage immediately and permanent damage down the road.
As much as this seems like a lot of steps, it's not. Have some wine, take a shower together, have lube handy, and whisper "easy baby" and it's all taken care of.
Good luck. Let me know how it goes.
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reader, anonymous, writes (26 May 2009): Are you serious?
"I give blowjobs and want to recieve anal"
If this were a real question, i don't believe the above line would be necessary.
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