Cross-Dressers, Female Orgasms, Tandem Couples Erotic Massage And More!

Wow this was an amazing weekend and I just had to share a quick overview.  Hopefully I will have time to write about some of the stories in greater detail.

The fun started Friday night when I got to meet with my cross dressing friend/client.  I will write more about this on my BDSM site MistressIvana.me but suffice it to say – HOT KINKY FUN!!!

Saturday morning my husband and I went to a workshop to learn about orgasmic meditation.  This is the website of the organization that gave the workshop http://www.onetaste.us/index.php It was an amazing experience and I can’t wait to start OMing on a regular basis!

That evening we went straight from the workshop to the Bellagio to meet with a couple that wanted to receive sensual erotic massages at the same time from my husband and I.  It was very different because he only comes on appointments with me once in a blue moon.  The couple was amazing – I hope my husband and I are as connected and happy as they were after over 30 years of marriage!

Sunday was good and busy!  I got to give a cute young man amazing anal stimulation and have hot completely satisfying sex.  Then I met with a gent who has a pantyhose/foot fetish.  We stretched his boundaries a bit and then he stretched my behind a bit as we had an orgasmic greek session followed by a very deep and completely satisfying climax for him orally.

Yes, it was a good weekend!  Now to get the brakes fixed on my car:)

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Couples Pleasure Session

In preparation for a couples session I find out how long they’ve been together, what their current relationship is like, if they’ve discussed all the various foreseeable outcomes of our time together and a short sexual history for each of them.  We trouble shoot in advance the main issues that could crop up as a result of working with me and how to deal with them.  We do this via email.

Also it’s ideal to work with me for a series of sessions many of my clients come in from out of town and can only see me once.  Over the next week or so I will be sharing the process I recently went through with a couple that worked with me.

I get to the room and introduce myself and talk a bit about my week and my background to set the tone of friendliness and support.  Through discussion with her I determine her true level of comfort – up until that point I had only interacted with the husband through email.  I explain my boundaries and goals for the session.  I make sure she knows this session is about them and their pleasure, not mine.  I will be interactive only to their comfort level and at any time that could increase or decrease and that is okay.  We will have constant communication throughout the session to check in on how they are feeling and let that be our guide.

I explain to them that there are several reasons that bringing in a professional is a great choice:

  1. By having a session you are putting your experience into a container that has a beginning and an end.  Afterward, you can review what you liked and didn’t like and there’s not a lingering question of whether the experience was complete or not.
  2. You won’t be worried about any emotional romantic issues coming back to haunt your marriage.
  3. It’s a more relaxing situation than trying to pick somebody up in the bar and not knowing what you’re going to get – what their skill level is sexually or what their motives are.
  4. Whatever pleasure I give to one partner the other partner gets the credit for it.

We review their interests as a couple.  He loves massage and all touch so he will be getting a full body sensual rubdown.  Then they want to review different handjob and blowjob techniques.  For her turn she wants to be pleasured.  She’s never “been with a woman” before and this has been a very exciting idea for the two of them.

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Their comfort level is full nudity.  I set up the massage table and gave him instructions to undress and lay face-down while I used the restroom and wash my hands.  I come out nude and begin the massage while she sits on the bed.

As I massage him the three of us discuss our sexuality.  I ask questions about successes and challenges and share my own.  By having such an intimate atmosphere they are able to open up quickly and we are able to discuss things on a very deep level almost immediately.  When I get to the buttocks area I demonstrate and explain slow, loving touch that will be easy for her to do and very sensual and pleasurable for him to receive.  Sometimes it’s better to go slower and softer.  He likes anal stimulation but she doesn’t love to give it – she will do it sometimes as a treat.  I suggest they incorporate gloves in the bedroom.  Using gloves will increase her confidence that she will not inadvertently hurt him and it will reduce her concerns about messiness.

I demonstrate how to slowly approach the anus, massaging first the place where the legs meet the groin, the sits bones and the entire crack.  Soft long strokes one after the other relax and arouse him.  Shorter deeper strokes massaging all the muscles in the crack relax and arouse him even further.  He is going with the flow of arousal and enjoyment, opening his legs further and tilting his pelvis higher.  Applying lubrication directly to the anus I massage his outer sphincter in every direction, gently stretching and massaging it.  I get even more lube and without penetrating I press inward against his anus with the flat of my thumb.  He asks his wife to come and massage his balls.  She stands across from me with her hand on his scrotum and he reaches back and holds her other hand with his.  Their love and connection is beautiful and I’m loving being a part of it.

He’s ready for penetration and I point my thumb tip in ready to slide it into his anus.  I instruct him to take a deep breath and on his exhale I slide my thumb into him.  I stay there and just hold him, feeling the arousal running through him.  When a person is this aroused stopping and holding can be very pleasurable for them as their muscles flex and relax themselves creating their own internal massage.  Then I gently pressed in every direction.  Envisioning a clock with the tail bone being 12 and the prostate being 6 I stop at each number of the “clock” checking in with him asking how it feels.  He said good a few times and I asked him to rate it on a scale of 1 to 5, 1 being not painful – that there might be discomfort but not pain and if there was any pain we needed to stop and address it immediately – and 5 being total bliss.  I continues around the “clock” and when I was twisting my wrist completely I gently pulled out my thumb and inserted my index finger.

I explained in between stops that this was extremely therapeutic – I was massaging all the pelvic floor muscles from the inside.  The arousal helps to facilitate a better pelvic floor massage because the pressure is pleasurable instead of painful.  At the prostate I touched each side and did a few different types of strokes all the time communicating with him about how each felt.   I also slid my finger in and out of his anus and asked if he liked that sensation (he didn’t).  Then I asked if he felt complete and since he did I ended that part of the treatment with gentle holding while his wife held his scrotum.

I had him move to the bed and lay on his back.  I sat cross legged on one side of him and she sat across from me.  Giving her some oil, she showed me what she normally does when massaging the groin area.  She had a great pace and touch.  I showed her several strokes, first demonstrating and then having her do them.  She was a natural!

I asked him if he thought he would like to climax and if so how he would like to do that.  He said yes and he’d like oral.  I double checked with her to make sure it was still okay and after receiving her nod of approval I bent down and took him into my mouth.  While giving him a wet, slow blow job I listen to them talk to each other about how each feels about having someone else sucking on him.  They both agree it is very hot and she says she is totally turned on.  With his cock still in my mouth I look into her eyes and reach a hand up to stroke her breast, gently scraping my nails over her nipple.  Then her husband was encouraging her to kiss me so taking my mouth off his cock I leaned across him and held my face forward letting her soft lips meet mine.  She was a fantastic kisser and after pressing our lips together we naturally opened our mouths letting our tongues touch and taste each other.  After that gentle french kiss we looked to her husband for approval and he told us it was beautiful.  I moved my hand to the back of her head letting my fingertips slide into her long hair.  I got a good grip and gave it a gentle squeeze pleasurably pulling on her scalp as I peppered her face with soft little pecks before returning to a full open mouthed kiss for the shared pleasure of the 3 of us.

His time came to an end and it was her turn.  We got very close and allowed the erotic energy to build between us.  I touched her sensually heightening her arousal.  I had her lay back on the bed and lightly ran my hands up and down her body touching everywhere but her breasts and pussy.  Each time the stroke went past I edged closer and closer until I was getting the full reactions of arousal – stretching her spine, clenching and unclenching her thighs.

I demonstrated and explained a variety of strokes to massage the vulva.  I thoroughly massaged the mons, the outer labia, the inner labia and the space between the labia.  I explained how these techniques could be used with oral as well.  Her arousal was high and I massage her clit directly, first rolling the shaft back and forth.   Then, gently holding it between my thumb and index finger I stroked it like a little tiny cock.  Using one hand to pull the hood back and exposing the glans of her clit I got extra lube and massaged it directly using super lite tiny little strokes.

Putting my face right in front of her pussy I gently blew on the entire area.  Getting my mouth full of saliva I stuck out my tongue and licked her outer labia up one side and down the next several times.  I breathed in her scent and exhaled warmly to add even more heat to her pussy.  Sticking out my tongue even further I dipped it into the crevice between her inner and outer labia and ran it up one side and down the other trailing below her hole across the perenium on the bottom and over the clit hood on the top.  I tasted her tanginess and kept the ovals going until I couldn’t taste it anymore.  Then I moved on to her inner labia.  They were nice and thick and pink and first I sucked on one at a time and then gently used my teeth to scrape and suck simultaneously.  Then I sucked both of them into my mouth and alternated between sucking and gently nibbling and worked my way up to her clit hoof.  Reaching the hood I made wet circles around her clit over and over.  Then I licked directly onto her clitoris, gently at first and then slowly building up pressure pressing in toward the center of her body.

I asked if she felt ready for penetration and she definitely was.  I inserted one finger and explored her vaginal opening massaging the urethral tissue and the surrounding erectile tissue.  I asked her what felt better and applied pressure at various depths.  After finding the best spot I did several different types of strokes and asked her what felt best.  Having discovered that I rhythmically rubbed inside her pussy with one hand and using my other I rubbed her clit.  After awhile I explored deeper into her and found her cervix.  I asked if it felt good for me to touch it and demonstrated several different strokes and  pressures.  With my hand so deep in her I was able to use my thumb to stroke her clitoris on the outside as I simultaneously massaged her cervix deep inside.

She became extremely aroused and then there was a change in her.  She wanted to cum but wasn’t cumming.  Her husband suggested the vibrator and the deep private issues started coming out.  She shared about how she didn’t like having to use the vibrator, that somehow it made her feel like less of a woman since she couldn’t achieve orgasm “naturally”.  I listened to  her.  I let her know that I heard her and understood her and could totally relate.  I’ve had the same issues myself.  While continuing to gently and lovingly massage her vagina and vulva I shared my learning in this area.  As I shared each insight I asked her if she could relate or if it made sense to her.

I’ve learned that I put a lot of pressure on myself to reach orgasm.  If I masturbate or have sex and don’t have an orgasm there’s a part of me that feels like it was a waste of time.  But it usually also seems like the harder I try to reach orgasm the more difficult it becomes.  The feelings of frustration and impending disappointment coupled with harder self stimulation just makes it worse.  And then, once and orgasm comes I feel totally sore – in my vulva from the rubbing and in my arm and hand from the exertion.

I found out that I need to be more loving to myself and accepting.  I am not vibrator dependent for my orgasms but there is nothing wrong with it if you are.  Some people are dependent on more extreme things than vibrators!  Imagine not being able to climax without being bound and gagged!  Or, like many men, being completely dependent or pornography.  The self – judgment about the vibrator is coming from some beliefs and old programs that aren’t working anymore.  Beliefs can be changed!  Start looking at the vibrator as a tool and having gratitude that it is so accessible.

I also learned a lot about myself during a 30 day masturbation meditation practice.  I practiced mindful masturbation everyday for 30 minutes.  I went through a lot of emotions and beliefs but the outcome was amazing.  I suggested she do it for several reasons.  She would get to know her body more intimately and that would make intimacy with her husband more pleasurable.  Being mindful masturbation, there is no goal of orgasm.  Because of that she would be giving herself permission to just feel the pleasure and enjoy the pleasure.  She might even find out (like I did) that she is having orgasms that she’s not recognizing as orgasms because they are deeper and subtler.  Before my masturbation meditation I only recognized clitoral orgasms but now I also recognize the cervix and g-spot orgasms that are not as sharp and all-consuming.  Another benefit of the practice was my vulva became more sensitive and that also made partner sex more pleasurable.  I was able to see how self massage could arouse me and how self pleasure could be pleasant even without the sharp climax of a clitoral orgasm.  On day 17 a change happened for me and it was like my pussy woke up!  I was stimulated easily and from a variety of things from walking and riding in the car to solo sex and partner sex.  Another benefit of the daily practice is that the pressure for a good experience is removed.  If you have a session that is less than ideal then no big deal since you’ll be doing it again the next day.  Also, doing it everyday gives you the space for experimentation – using different lubes and toys, different types of touch or different fantasies.  Using a mirror and seeing yourself and connecting with yourself is something you will have time to do.  There are many terrific reasons to have a mindful meditation practice!

Our time came to an end.  I let them know they could email me or call me if they had a  few questions or if they wanted more guidance I’d be happy to work with them on that level.  I wished them luck on the tables so maybe they could see me again before they had to leave town.