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In her free time, she can be found reading self-help books and romance novels, bench pressing, or pole dancing. Follow her on Instagram.

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Medically reviewed by Carolyn Kay, M. And 9 Other FAQs. 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.

If only it could always be so good. Veronica months ago permalink. 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 72 months ago permalink.

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. 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.

To ease the pain of anal intercourse use any product with Lidocaine. Lidocaine mixed with vasoline. Make sure nails are smooth and not too long 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 37 months ago permalink.

I did not prepare I wanted to feel like a virgin and have the pain turn i8nto pleasure 15 months ago permalink.

Still waiting for my first time 14 months ago permalink. 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 14 months ago permalink.

Never but think I want to 14 months ago permalink. Thanx for advice xdresserrandi 14 months ago permalink. I so looking forward to having my cherry popped.

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 month, I was addicted.

Yes it takes some prep, to keep things clean, but it is well worth it. After a few years, she introduced me to a man. In some ways it was the same as a dildo but, in other ways better.

I loved the warm feeling of having him inside me and and cumming inside me. While being with a man was pleasurable, I love being with my wife so much more.

I have had anal sex but first time with a guy with a monster cock any advise 4 months ago permalink. Yeah don't do it!!

It's best if you're guy eats your gurl pussy this will relax you then use plenty of lube and go slow 3 months ago permalink.

You gotta practice with toys on a regular basis with a ton of lube before you give it up for the first time.

I often work my boi-pussy a bit with a medium-size dildo before my guy and I connect; sometimes I'll pop in a small plug to keep things wet.

Lots of practice with toys; milady managed a bit of it with me using a strap-on, but by the time it actually came up with our guy, I had primed myself while we attended to her, and when I presented my wet bottom to him, he slid in easily even though he's quite a bit larger than my pink dildo.

My First Time with a Man… I had been chatting with a guy who was in town for training from Las Vegas, he was staying at a hotel near the airport.

Anyway after chatting online with him for a week I finally agreed to meet with him. So the day and time came, I was going to meet him at his hotel room about 4 pm, this was in late August, so still full daylight at that time.

Since I was going to be out in public, I really wanted to blend in and not call attention to myself in case I had to go through the lobby… He said that he would go and prop open the side door so that I could just walk in and down the hall to his room.

He would have a drink ready for me as he had picked up a bottle of Seagram 7 and some 7 Up. Anyway, I had dressed in a light weight skirt that went just below the knee in light blue and a peasant top in white with little flowers, suntan pantyhose and a 3 inch heels, lastly a pair of sunglasses with a white frame.

In my bag, I carried a black garter belt, black stockings with back seams, black thong and bra and a sheer black nighty, and a pair of black pumps… The plan was to change into this if things felt right after chatting and sharing a drink.

So I arrived on time, and true to his word, the side door was propped open, and his room was about 5 doors down. I got to the room and knocked, Jim opened the door and much to my surprise he was exactly as he looked in his picture that he had sent me.

He invited me in and he was dressed in the hotel robe and had showered before I got there like I had requested. The room was nice and it had a small table and a couple of chairs, so he made us drinks and we sat across from each other and chatted about many things and we eventually got to why he was attracted to me and why I agreed to meet with him, especially given my concerns about him never being with a CD before.

Half way into our second drink, I excused myself to use the restroom, I grabbed my bag and closed the door behind me. I quickly changed and popped a couple of breath mints and walked out….

At this point I think is when I actually stopped being just a Crossdresser and actually began my path to being a Transvestite.

He lead me over to the bed and we stretched out on it and continued making out like a couple of teenagers, his hands were all over me, caressing me and pulling me closer.

I was also holding and caressing him as well, running my fingers through his chest hair and through his hair on his head… Finally opening his robe and feeling the heat between his legs.

Half stood up on the bed and removed his robe and as he laid back down next to me and kissed me some more, I began kissing him from his lips down to his cock.

He was only partially hard, so I took him into my mouth and began to suck and lick him… I was overjoyed as he began to grow in my mouth, the more I sucked the harder he got, soon he was pumping away and I was enjoying receiving him like this, he stopped and pulled me back up to face me and kissed me again and asked if I would like for him to enter me and in what position would I like it….

I told him I wanted him to take me as a woman, face to face with him on top and me on my back with my legs on his shoulders. He agreed and got out a condom, which I opened up and rolled down his fabulously hard, full, eight inches of manhood.

He slid his cock into me, oh so slowly, I could feel every wonderful inch, every contour, every vein…. He reached over and pulled me face to face and started kissing me all over again, saying that I was so wonderful, and he really, really enjoyed our love making.

I pulled myself up and rested against the head board and spread my legs, he slid down and began sucking me off, his head bobbing up and down in between my legs.

Soon I was about to cum myself, and I told him so, but he just kept sucking, more and more… and then I did, to which he drank down every bit of my cum….

He got up, made up to fresh drinks and I laid in his arms until we finished those drinks. I got up and went to the bathroom to redo my makeup and change.

Lube will also prevent painful tugging and tearing of the skin. Put lube directly on the asshole itself, and onto the penis or condom.

Use a lot. Trust us. Dictating the pace and depth of penetration will minimize pain and ease any lingering nerves. One of the best positions for first-time anal is doggystyle.

It allows the catcher to be in control of the movement, and go as slowly as possible. Plus, doggystyle helps open up that whole area back there.

The receiver should focus on keeping their muscles relaxed. You may feel yourself instinctively tensing up, so keep taking deep breaths and trying to release that tension.

Keep working your way down the shaft of the penis slowly. You want to avoid pulling all the way out and pushing back in this can lead to pain , so try to limit thrusts to a small range of motion.

Doggystyle and side-by-side are easy positions to do this. Having something that girthy exiting your anus can feel a little strange, but slowing it down will make it feel much better.

Wipe yourself off with tissues, then take a trip to the bathroom to clean up more thoroughly. I got to the room and knocked, Jim opened the door and much to my surprise he was exactly as he looked in his picture that he had sent me.

He invited me in and he was dressed in the hotel robe and had showered before I got there like I had requested. The room was nice and it had a small table and a couple of chairs, so he made us drinks and we sat across from each other and chatted about many things and we eventually got to why he was attracted to me and why I agreed to meet with him, especially given my concerns about him never being with a CD before.

Half way into our second drink, I excused myself to use the restroom, I grabbed my bag and closed the door behind me.

I quickly changed and popped a couple of breath mints and walked out…. At this point I think is when I actually stopped being just a Crossdresser and actually began my path to being a Transvestite.

He lead me over to the bed and we stretched out on it and continued making out like a couple of teenagers, his hands were all over me, caressing me and pulling me closer.

I was also holding and caressing him as well, running my fingers through his chest hair and through his hair on his head… Finally opening his robe and feeling the heat between his legs.

Half stood up on the bed and removed his robe and as he laid back down next to me and kissed me some more, I began kissing him from his lips down to his cock.

He was only partially hard, so I took him into my mouth and began to suck and lick him… I was overjoyed as he began to grow in my mouth, the more I sucked the harder he got, soon he was pumping away and I was enjoying receiving him like this, he stopped and pulled me back up to face me and kissed me again and asked if I would like for him to enter me and in what position would I like it….

I told him I wanted him to take me as a woman, face to face with him on top and me on my back with my legs on his shoulders. He agreed and got out a condom, which I opened up and rolled down his fabulously hard, full, eight inches of manhood.

He slid his cock into me, oh so slowly, I could feel every wonderful inch, every contour, every vein…. He reached over and pulled me face to face and started kissing me all over again, saying that I was so wonderful, and he really, really enjoyed our love making.

I pulled myself up and rested against the head board and spread my legs, he slid down and began sucking me off, his head bobbing up and down in between my legs.

Soon I was about to cum myself, and I told him so, but he just kept sucking, more and more… and then I did, to which he drank down every bit of my cum….

He got up, made up to fresh drinks and I laid in his arms until we finished those drinks. I got up and went to the bathroom to redo my makeup and change.

This experience opened my eyes to what I had been missing out on all that time, what a fool I had been. Since then, any chance I get to connect with a man who can be that passionate about making love with, I jump at it!

Are you that passionate? Could it be you??? I am always looking for my next partner to make 'love' to What a wonderful passionate experience.

Very nice 2 months ago permalink. Ready and willing, tired of using toys. Oh, that was lovely!! Sign up for a free account, or sign in if you're already a member.

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North Carolina 0 replies. Any one from North Carolina here? Would love to chat by camokuntry81 7 hours ago. Nashville Crossdresser Wanting to meet another Crossdresser 0 replies.

Do you wear panties to work? I love to wear my cute thong under my work clothes. Makes me feel so naughty and CDing regularly, and what do we gain from it?.

I wonder how many of us crossdress on an average of 2 or more times a week? Chatroom 5 replies. Anyone know of any crossdressing chat rooms?

Profiles 7 replies. Why is it that a lot of people on Flickr. Don't fill out their profiles. So that Do you like to have sex dressed as a lady? Bottom replies.

Does others like to get dressed up and have sex being the lady. I love it. Traveling with breast forms 10 replies. So have any of you ladies gone traveling on an airplane with breastforms?

Has an Where to buy extra large wig???? The quickest way to find happiness in life is to find out what's real.

You are not a God, or a machine; you are an animal trying to survive in this place. So you need to realize that your first task is to adapt to reality.

Once you recognize that, you are able to throw out all the irrelevant material and focus on that task. Next it's important to know what "adapt" means.

It does not mean be spineless. It means take care of business. You may level the trees and start a farm, but you're going to have to plant seed at the right time, or no food will occur.

In society, you may find yourself leaving a bad job for a better one, moving to get away from idiots, or taking action against people who are doing something illogical.

You will need to do all of the above. You know what to do by picking what you can change, and what you cannot. You cannot change the seasons; you can change what you plant, who you associate with, what you buy and how you spend your time.

These seem like paltry weapons, but they are not. As you improve your circumstances, you also give yourself a voice of reason and others will emulate you because they too want to succeed.

When you have learned this lesson, you will also learn a corollary. There are two types of people you will meet in life: those who adapt to reality, and those who want reality to adapt to them.

Those who adapt to reality consider their situation, make goals, and proceed systematically. Those who do not feel entitled to certain things they can demand from society, but those are never enough, and as their lives become more disorganized they become bitter.

No matter what fond notions people pitch to you of equality, and of being fine just the way you are, life is a struggle for adaptation. Those who rise are hated by those who are too delusional meaning: they want reality to adapt to them to rise.

Not everyone can rise and not everyone will. At some level, this rising is binary: have you reached a situation where you have what you need materially, are content and like what you're doing?

You will find that people who are not content have made themselves discontented by their own hands. The challenges of life were not fun enough or too hard, so they spent excessive time pursuing their vices -- distractions, intoxication, fornication, self-deception.

As a result, they never get anywhere, and have to find something on which to blame their failure. They hate government, they hate nature, they hate society and, if you are content, they hate you.

If you have more than them materially, are more content within, are smarter or better looking, they will try to smash you. The dumb ones do it with violence; the slightly smarter ones do it by forming social groups with which they can mock others.

They feel empowered when they say "But all of us don't see it that way! Remember, they're expecting reality to adapt to them. Time will of course prove them wrong, and they will end up looking over a life that wasn't what they wanted and will have to face at some level that it wasn't what they wanted because they did not organize themselves, adapt to reality and create what they really wanted.

In some cases, self-deception prevented them from seeing what they wanted. Still others were fooled by going along with social groups based on delusion.

But in the meantime, we are all ranked by our actions. Someone disorganized but given to pursuit of excessive pleasures stands below someone who took care of business first, and then was able to have time for pleasures.

We are ranked by wealth, but this becomes unimportant if you have enough to live on and like what you do for a career. We are also ranked socially, and as celebrities by the media, but it's unclear if this makes people happy.

As you ascend -- in wealth, in personal organization and discipline, in abilities, in social status -- you will find that anyone who did not do what you did resents you and will try to pull you down.

Mostly, they do this through passive sabotage: "You can't really like that new job, you're working all the time! Underneath their friendly demeanor however is a singular goal.

They resent what they cannot have, cannot face the fact that they don't have it because of their own disorganization, and they want to destroy those who have anything so they feel better about having nothing.

This motivation underscores almost all human conflict. Probably the most controversial part of this lecture is the idea that happiness originates outside of the self.

People who are disorganized will tell you that happiness occurs when you have the right toys, intoxicants and social status; organized people will tell you that happiness consists in finding a place in life.

Place consists of career, family, friends, abstract goals and community. Career is easy: find something you like to do that is valuable to others, and you will get good at it and be rewarded.

Family is handled in a later lesson. Friends are those who want you to succeed because they are sure they will succeed as well.

They are comrades and equals in the oldest sense, which means they are of the same quality of mind, body and character as you are. Friends never sabotage you.

They are not there to help you do what you cannot do otherwise, but they as equals may trade back and forth information about how to live, in a playful struggle that makes you both better.

Abstract goals: this is the category for your music, writings, or technologies you develop that are not necessarily tangible.

These are areas in which you compete against yourself to make something great, and you do not expect reward in your lifetime.

These are gifts to all of humanity so it may learn from your experience and the wisdom you derived. Community: You may be sick of many of the people around you.

A community is made of individuals, but it is larger than any one individual. The people with whom you collaborate to keep society functional, and the people you enjoy, and the slice of civilization that is local to you comprise your community.

Community-building activities include reinforcing infrastructure, adding knowledge, helping those who are going somewhere to get there faster. If you try to live only for yourself, you will find your goal reduced to pleasures and comforts.

When these are achieved, you have nowhere to go. You become stagnant. Even more, you're isolated within yourself because others don't care and there's no lasting importance to what you're doing.

If you get over your fear of being proven wrong, looking stupid or being unpopular, and act to make constructive changes in your world, you create a feedback loop between the reward of seeing your work pay off and your own self-esteem.

You are no longer just an atom. You have a role, a place, and you do things that make other people you respect enjoy life more. Maybe we should use scare quotes and say: Ignore other people and their "ideas.

Hollow modern people try to find reasons to justify their actions or rationalize their failures. While real thinkers work forward in time, hollow people work backward by trying to explain why they did something in reasons entirely different from their original motivation.

Hollow modern people, who come from that group which is irresponsible and can't get itself organized so blames you for its failings, have "ideas" which are this type of justification.

They're not thinking forward, to a goal, but defensively, as if trying to make the bad decisions they've already made valid with some fancy "logic.

These people are controllers just as much as a bunch of dudes in fancy uniforms with machine guns and an iconic, enigmatic yet threatening symbol.

They are bullies. Their job is to belittle you, sabotage your confidence, and make you feel as if you owe them something or should pay attention to their ideas instead of your own.

If you doubt me, compare their ideas to the vast store of information that has withstood the centuries. You'll see quickly these hollow ideas fall short.

People who dislike life tend to be deconstructionists, and to embrace a liberal philosophy to make it sound good. Liberalism loves deconstruction, as the resulting chaos makes individuals feel they are hidden in a crowd.

As you go through life, people are going to ask you what you're up to, and some of them will then attack with their own "ideas" to destabilize you.

You might think you should carefully consider these ideas so you've got a balance of perspectives. Why do that, when all the classics of philosophy, literature, politics and economics are open to you?

Instead of staying in the social reality sphere, crack a book and learn from the true masters. The ultimate taboo in our society is pointing out that genetics, not wishing it so, make us what we are.

However, to really succeed you need more than genetics, and more than "hard work" -- which is rarely hard, but people reference it because they like the idea that putting in 70 hours a week at the office makes a moron rise above a born genius.

You need self-discipline. This means being organized, systematic, diligent and alert. Reams of paper and years of human-hours have been devoted to debunking the obvious truth, which is that intelligence is congenital.

You are born with a varying degree of it, and while you can refine this ability with education and diligence, you never get more than you were given.

It's like artistic ability. Someone born with a gift for music can choose to take up an instrument or not, and won't succeed unless they work hard, but they'll then be ahead of those without the gift.

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