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The Graduate Guide To Advanced Sexual Positions

Posted by TooTimid Staff to General / Misc Info
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Trying new positions is a great way to connect with your lover – and trying more “advanced” positions is a great way to have F U N in bed, and find a position that will stimulate you in no other way.  I caution you, these positions may take a little finagling to get into –but the reward is often worth the effort!


Sex Position Diagram
This Kama Sutra inspired position is WONDERFUL for both the man and the woman.  It is not the most complex position that I will talk about, but it is a great place to begin.  This position works best on a harder surface – like the floor – and requires a bit of flexibility.  The woman lies down on her back with the male kneeling in front of her.  She scoots her butt up against his penis for insertion and then she CROSSES HER LEGS at the ankles, bringing her knees slightly forward and resting her feet on his chest.

What this position accomplishes is deep penetration.  The vagina becomes open to him because her legs are slightly apart.  He can thrust in and out at a slow or faster pace.  This is a great visual position for the man and a wonderful position for adding clitoral stimulation if needed.  Plus, she can raise and lower her hips to grind up against him if she likes.  Intimate position with a wonderful reward!


Intimate Sex PositionGetting slightly more complex, this position is a good one for those women who liked to be “controlled” by their lover.  The woman lies on her side (either one) and bends her top knee and pulls it toward her, leaving the other leg straight.  The male gets between her legs, on an angle behind her, and enters her from a downward position.  Then, the woman stretches out the arm that is on bottom and lays her hand on it, while the male pushes down on her shoulder to keep her in position, thusly immobilizing her other arm as well.

This position is not very intimate – but can be very exciting!  Being positioned this way allows for an interesting sensation during sex as the thrusts are more shallow, but can hit the G-Spot if he goes in just right.  It is a wonderful position for light bondage play because the very nature of the position provided the “binding” experience.


Advanced Sex PositionsThis position is a variation on another Kama Sutra position and requires a bit of strength and flexibility.  The man kneels but keeps himself up on his knees, so his body forms a sort of backward “L” shape.  The woman, lies on her back and the man enters her and then picks her UP so that her back is arched slightly, her bottom meets up with his penis, her legs are bent and on his chest and she can grab his thighs with her arms for stability.  When the position is complete, the couple looks like the letter “B.”

This is a GREAT G-Spot position as well as a great Anal position.  While the man has to be able to stay UP on his knees while supporting the pressure of his lover pressing against him, he will gain a great view of her as well as his penis entering her vagina.  This might not be the best “long session” position – but it does have a lot of reasons to try it – the G-Spot orgasm being one of the biggest.


Intimate Sexual PositionsThis position can be obtained by either starting in the “B” position or all on its own.  This variation of the Kama Sutra’s “Cave” position is another interesting and fun one to try.  The woman, once again on her back, allows her lover to hold her feet up and open while he kneels before her.  She is entered by him, and then BENT backwards so her back is curved and her feet are by her head.  He then leans over her, between her legs, so that he can look down at her face.

The reason this is called the See-Saw is because you can not do regular, deep thrusting, but instead must “rock” back and forth like a See-Saw to get the penetration.  An intimate position, this position can leave women who are not “flexible” or who are a little ‘larger’ in the tummy region, out of breath and sore.  This position is definitely designed for those flexible gals who don’t mind being ridden!


Couples Sex PositionsSince I totally believe that some of the best sex can be done OUTSIDE of the bedroom, the next 2 positions utilize other rooms – and other furniture – besides the bed.  This position works best in a dining room chair – chairs can be soooo nice for positions like the Lap Dance.  This position, however, requires some flexibility and strength – as it is an advanced position.  The man sits on the chair, with his butt toward the front.  The woman climbs atop him (facing him) and he enters her.  Then, slowly and carefully she puts one ankle at a time on his shoulders while leaning back on his knees for support, and he holds her sides for support as well.

This position is a high friction position – where the fit of the penis into the vagina is very tight.  It can be made tighter by her squeezing her thighs toward his face.  This is an erotic position where he can see everything that is going on, and she can look at his face while they are going at it.  This position requires strength, but is well worth trying if you can get yourself into it.

Sex Positions To Give Him A Sexy Show


Chair Sex PositionThis position is rightly named because not too many ‘sane’ or practical lovers will try it – but it is a fun one – even if you can only manage it for a while.  Again, using a chair, brace the chair up against a wall or door.  The woman steps UP onto the chair, the man coming behind her.  She lowers her butt down onto his penis while leaning back against his chest for support.  He, being the strong man he is, holds her by her bottom as he thrusts UP and she bounces DOWN.  If you find this position has him slipping in and out, she can open her legs more and kind of “squat” down.  The reward is in the accomplishing – and the fact that you are both “totally bonkers” about sex!


Chair Positions For SexOne more position with a chair – I promise!  This position is FUN – and great for anal or vaginal penetration.  Placing the chair on a secure surface and braced against something, the woman gets up on the chair and faces the wall.  She bends down in a squat and her lover enters her from behind.  This position is great for those DEEP penetration moments; she can bounce, squirm, or buck up against him.  He can hold on to her hips for a wild ride.  Anally, this is a great position for both partners.

The wonder of this position is that the woman can open her legs more (in a froggy squat) or tighten them up.  She can straighten her legs and bring herself to her lover’s mouth for before or during oral sex.  He can penetrate her with his penis and digitally with his fingers.  Overall, this position is a great one for all sorts of fun!


Top Sex PositionsOk, now we are getting into the nitty gritty positions – those that you would see in a book and go “huh?”  “How?” or “NO WAY!”  I have tried this position successfully and it is worth it, if you can get it in.  The man lies on the FLOOR – no bed here ladies – and bends his knees toward his head, rolling his back.  His penis will appear between his legs and his lover then “sits” on him with her feet bent as if she was sitting on a chair.  Yes, it is odd, and yes, the penis will go that way.

This position is fun, but not overall stimulating for the man.  He can watch his penis go in and out of her vagina, she can control the speed of the bounce and grab his balls if she would like.  Most men can not sustain this position for very long, so it is more of a novelty position for him, and a “getting things going” position for her.  Hey, you got to try it, because it is unusual and don’t we all want to see our man getting “sat” on!


Unique Sexual Position For CouplesBe forewarned, the woman has to be fairly petite to make this position comfortable.  The man will lie down on his back on the bed with his legs dangling off the edge at his knees.  The woman, then climbs atop him, mounting him slowly while he helps to balance her.  Then, she takes her legs – one at a time- and stretches them out by his face as she continues to sit straight up.

This position is great for those slow going nights.  Both lovers are fairly relaxed and can sort of “sway” back and forth to get penetration.  If your man likes to suck on your toes – this is a great position for adding that stimulation.  Also, if you want to, you can then just spread your legs for a wider penetration and he can sit up for that “face to face” girl on guy position that many couples like!


Extreme Sex Positions GuideThis position is FANTASTIC but is a little hard to achieve and maintain.  Definitely an “advanced” position.  The woman lies flat on her back, her legs slightly apart.  The man gets atop her on his hands and knees facing her FEET.  Then, he enters her in a downward fashion then stretches his legs out to either side of her face.  This is a GREAT position for melding the pelvic arch and clitoris and many women (including myself) report multiple orgasms!

In this position, the man and woman grind up against one another in a slow and sensual manner.  The woman has PRIME access to his butt – and can easily penetrate him with a finger or a toy.  Or, she can just grab and claw his butt – which adds to the heat of the moment!  I highly recommend this position for all couples to try – as long as your man is not too heavy and can support himself.  A variation on this is for the man to get up on his knees, bringing the woman with him, but that is a bit harder and not as good penetration is achieved.


Now, of course all of these positions are not obtainable by ALL people, but that is what is so great.  While you are trying desperately to get in and out of these positions you are connecting with your lover – playing with them.  They require teamwork and an open mind.  Feeling confident enough to get OUT of the missionary position and try something new is a wonderful experience for any couple.  Please keep in mind that many of these positions require flexibility and strength – so be careful!  Also, remember that neither Too Timid nor I take any responsibility for injuries that may be sustained by attempting any of these positions – try at YOUR OWN RISK!

In the meantime, try to step up your sex life and see what new heights (or lows) you can bring your lovemaking to!  Remember, have fun, connect and try new things to keep your relationship fresh, new and HOT!

Author’s Note and Credit - some positions taken from:

Superhot Sex by Tracey Cox
The Little Bit Naughty Book Of Sexual Positions by Siobhan Kelly

What's Your Favorite Position?
Let Us Know!


Date 6/26/2014
Please give some positions specifically for bbws.
Date 4/2/2016
The best part of chair positions is having something to hold onto for leverage and deep penetration
Date 7/18/2016
never tried any of these, looks fun

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