TS Dating Gude

America's Foremost Transgender Woman


stand up and take it like a wo-man

Most people find it surprising that one of the easiest ways to accommodate a large lover is standing up. 

First, stretch the muscles before hand. Just like loosening your legs up before running, you will need to stretch your behind to prepare it for any rigorous activity - and allow you to focus on the pleasure of your experience.

You can do this with your own fingers or some sort of artificial penis - I think you know what I'm talking about. Try to do this once every couple of days and reach a point where the initial pain from penetration is minimal.
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Second, try to stay clear of a John Holmes types your first time out. You might find a very large penis intoxicating sexually, but the term rip you a new ass hole will take on a vibrant meaning if you make this sort of person your first lover.

The key to achieving pleasure from being the recipient of anal sex is relaxation. If it's your first time with your legs in the air, this might be a little tough. The excitement over finally getting laid is usually a little overwhelming. No muscle stretches easily while you're tense. You might find a stiff drink helps shakes off some of the stress.
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Here's a helpful tip you can practice during your stretching exercises: First try to step away from the intensity of the moment and take your mind to a relaxing place - or memory. As you feel your body going limp, take a deep breath and slowly - exhale fully. It is at this moment, with proper stretching, you can accept almost any sized lover. Don't be concerned you're not being a hot little vixen - you'll have plenty of time to enjoy your little ride, as you get accustomed to the size and length of your lover.

Finally, get in the right state of mind. As I mentioned before, your anal muscles are controlled by your mind. The entrance stays shut because your mind tells it to do so. Opening this area is all in your head. There are two factors involved in letting go. The first has to do with your mental imagery of your ass. As adults, most of us are taught that it is a dirty place to be and we naturally tend to keep it clammed up. In reality, it is one of the most sexually sensitive loins on your body - second only to the female clitoris in terms of the number of nerve endings. 

Second, the method of cleaning for both health concerns and your own sense of confidence.

Third, is the physical aspect of stretching.

You can numb the pain with alcohol. Some people will even use poppers to get them past the first pain from penetration.

the ride of a lifetime

Okay, he's inside, now what? Hopefully your lover will take things slow enough for you to get used to his size and length. In case you, or he - is not aware - different positions can cause a lot of new found pain - as you get "stretched" in different ways - both inside and out. If not, remind him of this if you experience any such pain.
shemale.

First thing to remember is your hole is situated lower than a vagina thus your legs will need to be higher in the air than your female counterpart. 
 
Use every tool available for your pleasure and his. Most girls will not be able to orgasm from penetration alone.  

As a final note, most people agree the best position for a first timer, is lying face down on their stomach - with a pillow under their hips. This position is usually the least painless to be penetrated. Once you have loosened up a bit, you can contort your body any which way you like.

Cheerleading - Talk up a storm. I find I can get a lot of guys off (and sometimes myself) with just the words that flow from my lips during sex.

Let me begin by saying that anal sex is dangerous in a lot of ways. It's a very easy means to spread diseases. Some people assume it's just like vaginal sex. It is not: an anus is not a vagina. I know everybody knows that, but some people don't really "understand" it. Exactly how easy or difficult this process will be, depends on the size and length of your penis - and her prior experience with anal sex.
crossdresser
If you're a first timer in the role as a top, I can only offer one bit of advice: be gentle. When you're with a GG, you usually have to wait until she is well lubricated, before you start gearing to knock the bottom out of it. With a t-girl, it's a little more complicated.

The entrance to her backside is controlled by muscles. Just like the muscles in her legs, you must stretch them out, before any vigorous activity - or run the risk of tearing them horribly. Lubrication is important - but remaining calm and patient - is the best remedy for a girl who doesn't spend a great deal of time on her knees.

You first need to give her a moment to clean herself in the bathroom. Some girls prefer to stretch and lubricate themselves with their fingers, others enjoy their lovers to do this for them. Don't be afraid to ask.
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When you first mount her, don't forget she might need to adjust her equipment to stay clear of your movements. I think you already know how unsexy" a smashed ball feels. Take your time sliding inside her - and I mean SLOWLY. You may have to stop and start several times - in order for you both to get comfortable.

As she adjusts to your size and you are able to gain full penetration, don't get in a hurry to pound away. Sometimes, her insides require getting used to your endowment, in order for her to most enjoy your thrusts. Some girls are not able to remain erect while receiving anal sex. Don't take this as a sign she is not enjoying you being inside her - it's an individual thing. You might encourage her to touch herself as you have intercourse.

As both of you get accustomed to the pleasure, you can rearrange your bodies as you see fit. If you want to cum from being inside her, I'd suggest you position her on her knees, with you behind her. This will allow for the most controlled pleasure on your part by grabbing her hips and gaining better leverage. Just take it easy initially. Unless she is lying on her belly, this position will cause you to feel larger in her behind, and may require a bit of getting used to.

Of course, after you've had your big moment - don't forget to return the favor. Remember, she knows all about blue balls. LOL

it's all in the head

The size of a cock offers a variety of differences. If you are into anal sex, the size . 

Physical versus mental lovers. The opposite in the GG/Male sexual relationship. Those that tend to be very physical versus mental in sex.
 
masturbation

handy ideas 

In my opinion, masturbation is one of the most underrated forms of sexual intimacy amongst heterosexuals. Most gays I know - both male & female - use it extensively for sexual satisfaction. For some strange reason, it's never caught on as well amongst hetero lovers other than as a means of foreplay.

There are obviously two basic ways to enjoy this means of sexual gratification. One, is where you perform masturbation on your partner. The other, is where you touch yourself.

If you are going to masturbate your partner to orgasm, you'll discover that pretty much every -body tends to move their hand a tad bit differently from the next person. Although not required, your best bet is to use a hand lotion to provide a lubricant for your hands to slide most deliberately over the stalk of your lover . If a hand job is simply a warm up for deeper subjects, you'll want to use a lubricant that is also safe for your "insides". There are a variety of branded products for such activity - my personal favorite is WET. I always warm the lotion in my hands before applying it to the penis. You'd be amazed how even minor temperature difference can chill the moment. *G*

As your lover begins to get more excited, you will likely notice the penis will start to emit its natural lubricant or "pre cum". This is natures way of helping lubricate the canal to the urethra so the semen can most easily swim to the womb - and it also acts as a lubricant. Use the juice to lubricate the shaft. 

Unless you are certain the lubricant is warm and 

Females, in general are not as adept at this skill as t-girls. I wonder why? LOL They tend to be much more apprehensive in handling a penis, lacking the type of grip and exuberance to achieve orgasm. They fail to apply adequate pressure, often tug and even scratch in manners that provide anything but pleasure.

First, take a look at the penis in front of you. Note its shape and size - or flow. If you can grip it's width with a single hand, you task will be much easier as it is far easier to squeeze all at once. If not, use two hands. 
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Next - take your time. Men (as we know) are quite proud of their penises and appreciate it when another admires it. Do so. *S* Let your lover know you like it and are not ashamed, afraid, or disgusted by it in any manner.

Start in a slow deliberate motion, sliding your hand fully up and down the penis, and giving a tiny squeeze each time you reach the head. Add more lotion to maintain the smoothness of your caress, as your partner begins to get excited. As with oral sex, the key to sending them over the edge is to focus your final friction on the head of the penis. Try to increase the pressure of your grip as orgasm nears and with the aid of the lotion, keep slowing tugging on the head in a circular manner. You're hand won't be empty for long. ::))

One of my favorite methods in this department is the fist over fist method - where you use both hands and alternate sliding first one and then the other from the base of the penis to the tip. In this manner, you can strike up a similar rhythm to the single handed method but with the added stimulation of a second palm. To add intensity, try occasionally moving one fist down - and the other up - stopping to squeeze when each reaches the end.

One of my favorite forms of sex is mutual masturbation - where each person touches themselves. Lying side-by-side or sitting face-to-face, this can be highly pleasurable. The free hand can explore your partner's anatomy, while your busy hand times release. Personally, I find pleasure is heightened with a little dirty talk and some hot kissing. This is certainly one of the only ways to achieve cumming together with t-sex.

oral sex

the perfect blowjob
shemale sex
I personally can't stand the taste of semen. I have a weak stomach - and there is something about it that just doesn't sit well with my tummy. Some guys seem to get obsessed with having a girl swallow. If you like it, drink up GF! However, if you're like me, here's a few ideas on making the "non consumption" process - more erotic.

First, remember that when a guy has just cum. Come on girls, you know what I'm talking about. You're not that damn feminine, sweetie! ::)) Play with the stuff. 

Most guys are under the impression that since they have a male sex organ - they will automatically know what feels good to another individual with the same equipment. Problem is, they might know the feeling - but they often know zilch about how to deliver the goods.

During their first time with a t-girl, most guys are fixated with touching and tasting her penis. The unique combination of smooth skin, hairless scrotum, silky garments and the sex of a male is sometimes enough to make the whole event pleasurable for the guy.

 It's nice that you can have so much fun doing so, but it often does little for her, after the first minute or so. Everyone likes to know they're desired, but when your focus is more of an obsession, it reduces the pleasure.

The million dollar question: Can you give a good blow job? Have you ever had a bad blow job? Not fun, was it? A lot of men don't really know the first thing about the make up of their manhood - and thus a great number of t-girls don't as well.

 Let's talk about the art of giving a great blow job. First take a look at your own friend. Notice the area where the "cone" of the penis head comes together? This is the most sensitive point on the male body - loaded with nerve endings. Collectively, the head of the penis has more nerve endings than any other area of the male body. Learning to manipulate them, will take you a long way in becoming an accomplished cock sucker. ::))

One mistake many "newcomers" (no pun intended) make, is focusing on the shaft of a penis. As much as you might think "sucking up and down on the shaft" will cause an explosion in your lips, it's really just for show in the porno movies. Take a moment and touch your own penis through your pants. The excitement you'll note - is the slight amount of friction your head feels against the fabric - not the shaft. Your shaft has very few nerve endings.

One area than can be of additional benefit is the balls - but just be careful. We all know the wrong "move" can spoil a mood in a moment. LOL. Light caresses with the tips of your fingers is often the perfect touch to a good blow job.

When I start, I always prefer my lover is flaccid. A lot of guys don't like pulling out their penis when it's not erect, but I find this to be its sexiest state. It also provides me with my best opportunity to learn its individual; hot spot's - it's harder to tell such things when it's erect.

I usually like to start by admiring its features, weighing it in my lips, and using my tongue to find the most sensitive nerves. Watching and listening to your lover's sounds and movements, will tell you a great deal about how to get them off once things reach a fiery level.

When you think they are ready to come, focus, your suction in a rapid motion at the head of the penis - and keep fresh saliva pouring from your mouth to enhance the speed. A big mistake a lot of newcomers make here, is sucking "too hard" early on - and getting very tired in the process. It's the friction at the head - not the deep throating or the vacuum - that will cause ejaculation.

One the cum starts flowing, it's time to turn on the Eureka, Hoover - whatever brand of lungs you own. Nothing feels better at the moment of truth than a high suction finish.

Sexual Inter "Course"

Spreading your Wings

Anal eroticism can range from simply stroking your anus or your partners with a lubricated finger to actually sliding some fingers inside your partner, to full anal intercourse. All these things are physically pleasurable and if you practice simple hygiene techniques there's nothing repulsive about them.

The anal taboo is very old but there is no medical reason for it if you know what you are doing. Make sure you have gone to the bathroom before playing. Some people wish to use an enema to make sure everything stays neat, although this practice is relatively uncommon. In today's world, most couples use condoms during anal sex - regardless of their knowledge of each other's safety.
tranny trap
You should use plenty of water soluble lubrication when you try anal sex. Never use Vaseline or petroleum based lubrication products. I prefer both EASE and WET. Use LOTS of lubrication, it's clean. The more lube you use the more comfortable you will be.

Your rectum can receive a large penis easily and fully, and be pleasurable. The key to pleasure is you must want it. That is you must be at ease in mind and body. The rectum is very similar to an elastic pipe with a set of muscular rings at the end. The anus acts as a plug, to stop things from going out or let them in. It tightens and releases like purse strings on a bag and is fairly strong.

The muscle is controlled by the mind and emotions influence how tense it will be at any given time. Good fucking can't happen unless you are relaxed and this may take some learning. Many of us are taught to be ashamed of our rear ends, of the things that happen there and the sensations in the area.

The anus can be an erotic place. most children experience pleasure in shitting but many adults ignore these feelings in their rush to get the whole process and guilt over as quickly as possible. The rear end becomes an ignored and mysterious organ.

Awareness and conscious control of your anus can be learned, although this takes time to discover. Look at is as exploring something new part of your own body.
 
Anal sex can be as safe and enjoyable as any other form of sex - practiced properly. The anus can be an intensely erogenous zone. The anus contains more nerve endings than any other part of the body except for the clitoris. 

Without care and proper preparation it can be painful and even dangerous. All too often anal sex is a one time experience. In a typical scenario, the couple attempts to try penetration with little preparation. The one with the anus being invaded with little warning screams in shock and agony and swears never to try it again.

You'll quickly ascertain why rape is a capital offense if you ever let a less than gentle lover climb on top of you. I'm no slut - but I've had sex more than once. On one occasion, I endured such a lover - and it literally brought tears to my eyes. I was young and stupid. If it happened today, I'd still have his balls mounted in my trophy cabinet. 

A lot of girls fantasize about ending up on their knees or backs - getting screwed for hours like a GG. It's not unusual for a newer girls to imagine being tied up or controlled during this process.

Some girls consider a masculine male as the ultimate means of feminine intercourse, others prefer the idea of a GG with a "strap on", while most love the idea of another t-girl wearing out their backside. Whatever your idea of heaven is, you need to consider a few things before you part your thighs too wide.

First: You behind is NOT a vagina. It does not stretch anywhere near as easily, and losing your t-girl virginity can be a lot more physically painful than breaking a hymen. The entrance to your love hole is protected by muscles. Like any other muscle on your body, it can be torn - badly.
tranny
Most girls do not enjoy their first time being penetrated. They envision total pleasure - and experience absolute pain. The key to enjoying your first time has as much to do with what you do before you lose your virginity - than after. 

First and foremost is being clear on your actual desires - versus your inner fantasies. I hate to keep harping on this issue but I've just seen too many friends get really screwed up emotionally from the experience (literally & figuratively). 

Anal sex has a way of taking you places mentally you might do best to stay clear of. First off, a lot of girls considering this step are still searching for their own sense of sexuality

Anal Sex Tips for people not into pain
shemale trap

I've helped a lot of my straight girl sisters with discovering the joys of anal sex / anal play.


Anal Play for Anal Sex….penis penetration vs. rimming


Getting clean


Step One – you have to want to do it. If it’s just for your partner’s desire it might not work for you. Analogy / why?


Step Two – it’s all about relaxation…lots of people first try it all excited or geeked out. Expecting joy like they’ve watched in a porno only to experience SEVERE pain.

Positions – best for beginner is missionary + why

The inch at a time rule

You can’t use too much lube