It was something he never imagined he'd want, Rob, my strong, sexy, man opening himself to as yet unexplored desires; reaching deep within himself to uncover his feminine side and longing to feel how it would be to enjoy himself as "her". I couldn't think of anything more sensual that helping my man "doll up" to become the gurl he longed to be and had a night planned for him/her that was sure to be the beginning of a new chapter in our loving, committed and extremely erotic relationship! Living it out, which we did just a few weeks ago at the beginning of June 2010, with the help of some silky, sexy lingerie, a pretty wig, and an eager, young bi friend of mine, was just the first chapter in what will be a long and very naughty living story!
I had left some clothes out for her on the bed, a pretty white silk chemise with black embroidery, stockings, a long black silky robe. She had arrived only moments before me and was still catching her breath on the bed having changed just before I entered the bedroom. I greeted her with a passionate kiss, led her to sit in the vanity chair and applied finishing touches; lovingly adding a soft makeup pallet, a string of pearls, and a black bob wig to complete the look. She was so pretty all made up, like I knew she would be. Soft skin, pretty face, gorgeous eyes, her tall, lean body draped in satin and stockings; and the look on her face when she saw herself in the mirror, so pretty and feminine, my sweet Ashley, it made me so wet I couldn't wait to have her.
Feeling the satin rub against my body as we kissed and made our way to the bed, I could feel her nipples harden at my touch, her body shudder lightly as we lay together, hands wandering, caressing, kissing, teasing, in such delicious ways. I could tell how much she loved me letting her be the gurl she so longed to be; how her voice softened and grew light and higher as we talked and teased, kissed and caressed, her passion growing stronger and deeper, her desire to be a sweet yet very naughty gurl as she asked me to touch her pussy, rub it, see how wet she was getting, which in turn was making me wetter.
Removing her panties, it was like a moment of freedom for her as she went from the somewhat shy gurl to a craving slut in one quick motion; begging me in her sweet, lilting voice to lick her pussy. Spreading her legs, feeling my soft tongue licking, penetrating, she spread wider, lifting her hips off the bed as passion overtook her and she needed more, she needed to feel her naughty girlfriend tease and pleasure her with their strap on.
Almost as hot as the idea that Ashley wanted me to let her share that slim, sexy cock, was her putting it on me! When it was fully on, she begged me to let her have it, to taste it, suck it. I slowly climbed on top of her, moving up so her lips could begin to touch it, and all at once her hunger took over and she was sucking that cock like a luscious candy, sliding it in and out of her glossed lips, deeper and deeper, eyes closed, moaning; her whole body moving to the rhythm of her lips. I couldn't help but tell her how sexy it looked, how hot she was making me sucking and craving her girlfriend's cock, the passion building to a fevered pitch Ashley quickly got up, turned around on all fours and demanded "fuck my pussy, please, put your hands on my hips and put your cock inside me!"
Her desire so strong, her passion so great, I was wild with wet heat grabbing her hips, lubing up my cock as she had done to her pussy just a moment before, slowly sliding in the tip, listening to her soft moans as I began to push in more... more... her moans growing more powerful, stroking her own clit/cock as I slid all the way in, grabbing her hips, thrusting my cock deep inside her, over and over as she told me how amazing it felt, gasping for breath, stroking as I fucked her deep and hard until she lost all control, lunging forward as I thrust hard and she squirted her sweet, sticky juices, her whole body convulsing with pleasure, surprise, amazement and crazed desire. The first time I fucked my "gurlfriend" and we both loved it!
He collapsed on the bed, naked, regaining his manhood as we softly chatted and he relaxed under the strong yet soft touch of my massaging hands rubbing every inch of him from head to foot as he gently slipped in and out of sleep. Turning over on his back, I began the same massage when a text message came in for which I had been waiting. I read the message, confirming a plan I had been working on, and my noticeable smirk gave way to me telling him I had a surprise for him. Over the next 15 minutes, he gently tried to coax me to tell him the surprise. Was someone coming? Was it another girl? Was it the boi? (a reference to a much younger casual friend bi-friend of mine who had an interest in getting together with us). I teasingly held my ground, not revealing my secret despite his very cute begging questions and sweet kisses. But then he whispered gently as I was rubbing him down, "you wanted me to wait to suck my first cock to be with you, and I did, so you should tell me."
Being that we have a very open relationship, playing with others together and separately when/if the situation arises, knowing our hearts are completely committed to each other, the opportunity for him to venture into this new realm was available and I'd asked him to wait until we could share it together. Not because I didn't want him to do it, but because being part of something so new is exciting, and I wanted to share that with him. As such, his statement being true, I decided to share the surprise and told him that indeed, the young boi was coming in 30 minutes and he was dressing as a young gurl to play with his sexy momma and her gurlfriend Ashley.
After finishing Rob's massage, it was time to get Ashley ready for company. I brought out another new outfit for her to wear, nude thigh high stockings, satin panties, a soft navy blue chemise, laying on the satin bed coverings illuminated by candles, she was in her element and I snapped her first photo. The boi, though bi, had limited experience, as did Ashley, so he wanted us to already be playing when he arrived. We were kissing and touching on the bed when he pulled up and entered the front door. A minute or two went by and "she" came into the room, Chrissy, in a t-shirt, padded bra, black skirt, panties and a long blonde wig pulled in a low pony tail. Her face unmade but sweet enough on its own.