Crossing Over the Line


She leaned forward and clasped her hands behind my neck to hold me tightly against her breast. Katherine thrust her hips up against my hand and moaned again. She ran her hands through my hair, using her fingernails to draw a path through my scalp before sliding them back down my neck and pulling me tightly against her. I felt her warm tongue on my ear, drawing circles along the outer lobe before tickling the opening with the tip. The I heard her husky, sexy voice:

"Let's take this inside lover," she said then drew back a bit to look deeply into my eyes.

"Mmmm, I'd love to," I said, meeting her gaze with mine.

She slid off my lap, hands trailing down my chest, then playfully pressing and outlined the bulge in my pants with her fingers before setting her feet down on the floor and rising. She took my hand as I also rose.

"Take your glass and the Champagne. I'll take the bag," she said softly but with authority.

I leaned over to pick up my still quarter filled glass and realized that with only one hand free it would be difficult to pick up the Champagne bottle without risking spilling the contents of the glass. Not wanting to let go of her soft hand, I quickly downed the last two or three ounces of wine in the glass and then managed to hold the neck of the Champagne bottle and the stem of the wine glass in one hand as she led me by the hand down the hallway to her bedroom.

The door was open and we entered with Katherine in the lead. The room was even more dimly lit than the living room, a shaded, low wattage lamp in the far corner providing the only light. At first, I couldn't see anything but dark shapes. As my eyes adjusted to the darkness, I could make out a nicely made up double bed in the middle of the room with night stands on both sides. A mirrored wardrobe stood opposite the foot of the bed, a small dresser was behind us to the right along a short hallway that led to a bathroom.

Katherine led me to the side of the bed and told me to wait there. I set the bottle and glass down on the night stand and waited. I watched as Katherine removed the comforter and several of the decorative pillows from the bed, leaving only a fitted sheet and several regular pillows stacked up near the foot of the bed. She came back around to where I was standing, put her arms around me from behind and hugged me tightly, pressing her hard nipples into my bare back. I felt her hands slip down to my crotch and gently massage me, using her nicely manicured fingernails to trace the outline of my very stiff dick.

"Let go of everything Kelly - let me guide you. Just do what I say and you will have a fabulous time," she whispered in my ear as she continued to gently massage my cock through my pants and underwear.

"I'm all yours Katherine. I'm in your hands completely," I whispered back.

I felt her press herself against my butt and then gyrate her hips in small circles, letting me know exactly what she had planned for me. With her arms wrapped tightly around me, I had the wonderful sense of being engulfed by her. The combination of wine, the scent of her perfume, the warmth of her body and the throaty, whisper of her sexy voice had me slightly high and thoroughly aroused by now.

It was all going exactly as I had hoped. In arranging the session with her, I asked her to take charge of everything - direct me on what to do and how to do it. As a sexual submissive, I enjoyed the feeling of completely letting go - letting my partner take charge. I explained that I was not looking for her to be stern or abusive. I wanted her to be sexy, sensual, even playful but completely in charge of the session - basically to take her pleasure with me and provide pleasure to me how and when she wished. It was clear from her actions so far that she clearly understood the type of session I wanted.

I felt her hands move up to my waistband, undo my belt and the button of my pants and then slowly draw down the zipper of my fly, the soft "whirrr," of the zipper just audible over the sound of her warm breath in my ear. She slipped her thumbs into the waistband of my pants and drew them down over my hips, down my thighs and finally to my ankles. I felt her kneel down behind me and take my left ankle in her hand. I glanced down, saw what she was doing and lifted my foot up high enough to let her slip off my loafer and sock before sliding the pant leg completely off of me. As soon as it was free, I put my left foot down and raised my right foot. With practiced efficiency, Katherine removed that shoe and sock and slid my pants free of me.

I was left standing there in only my white briefs, now "tented" by my fully engorged pole. I was a little embarrassed to find a small circle of pre-cum wetness in front. Katherine stood back up behind me, put one arm around my waist, hand and fingers spread wide on my belly, lightly tracing a line with her fingernails until she reached my crotch. I felt a sharp tingle race up my spine and I shuddered in response. Her other hand slid down between my legs from behind, tracing a line with her thumb along my ass crack until she reached my balls which she cupped in her hand through the soft cotton of the briefs.

"You seem very happy to be here Kelly," she whispered and then chuckled at the obvious truth of her comment as my woody rested in her hand.

"There are no words to describe how happy I am to be here with you Katherine," I replied.

"Well, I am very happy you are here Kelly. This is going to be a very special afternoon for both us."

She released the hold she had on my cock and balls and told me to lie down on the bed, face up while she got comfortable and unpacked my gym bag. I climbed onto the bed and half rolled over until I was lying face up, lengthwise on the bed. I looked over at Katherine who was now putting on a bit of a show, giving me close-up view of her shapely, stockinged leg by putting one foot up on the bed and slowly caressing her leg from hip to ankle.

She took notice of my eyes glued to her leg as she showed it off and it gave her pleasure to see the excitement in my eyes as I watched her. She smiled at me as she unzipped her short skirt from the side and slid it down her legs, stepping out of it when it hit the floor. Katherine looked incredibly sexy, topless, wearing only stockings, garter belt and panties. She stood there a moment and posed for me, hands on hips, playfully turning a little to change the angle of my view.

"Now let's see just what you brought Kelly," she said as she picked up the gym bag she had previously set down by the night stand.

She put it down on the edge of the bed, unzipped it and began taking out its contents. Each item was in its own clear, plastic bag. In addition to condoms, lubricant and latex gloves, I had brought along several light bondage items. In arranging the session, I told Katherine that I liked some light bondage - nothing tight, painful, elaborate or inescapable. Just something to restrict my movement, provide at least the illusion that I was helpless to resist and was being "taken."

She opened the box of condoms and dumped the dozen square packets out, spreading them out near my hip. She looked at the two bottles of lube I had brought - one a nice strawberry flavored variety, the other a thicker, more viscous gel more suitable for anal play. She took a few gloves out the box and lay them near the condoms, tossing the box on the floor.

Unsure of a couple of items, Katherine took them out of their plastic bags to inspect them. One was a sex sling which she handed to me to demonstrate. It was basically a long nylon strap with velcro closure type ankle cuffs at each end, a padded section in the middle of the strap and adjustment buckles near the ankle cuffs. The idea was pretty simple - it was a device used to keep a bottom's legs up and spread when being taken missionary style. The padded section went behind the neck of the bottom, the ends of the strap went under the armpits, the ankle cuffs attached to each ankle with the legs up and spread. The top could adjust the length of the straps leading to the cuffs, shortening it by pulling on a tag strap by the buckle near the cuffs. The shorter the straps, the more the bottoms legs were pulled back towards the chest.

Katherine smiled while I demonstrated how it was used and then clapped her hands with glee as I showed how pulling on the tag straps shortened the sling, pulling the legs back. There would be no need for her to exhaust herself holding my legs up in a missionary position.

The other items she wasn't sure about were "post attachments." Basically short leather straps with a metal ring at one end and a clip at the other. The strap goes around a post - say a bed post, the clip passes through the ring creating a firm attachment point for a wrist or an ankle cuff.

The velcro closing wrist and ankle cuffs were pretty much obvious as to how they were used except these had double velcro closures - an inner one to secure the cuff to the wrist or ankle and a longer outer one that could be used to connect cuffs together through an attached d-ring in the other cuff before being re-secured to its own cuff. I also brought several items that could be used to put a bit of a squeeze on my ball sack. These included an elastic, bungee type cord - about the length and thickness of a shoelace, an elastic silicon ring and a loop (a small piece of thin rubber medical type hose - formed into a small loop with its ends passed through a small bead that slides up and down decreasing or increasing the size of the loop hole.

Katherine laid the bondage items along the edge of the bed, arranging them for easy access. Bent over at the waist, her breasts dangled and swayed with each movement. When she finished, she put the bag back down by the night stand and then climbed up on the bed. Moving gracefully, she slid over and straddled my ankles facing me, straightened and arched her back, thrusting her shapely breasts out, then provocatively ran her fingers through her long hair. Silhouetted against the dim lamp in the corner, her lithe body looked incredibly sexy.

Katherine paused for a moment in the arms up "glamour girl" pose before bending forward all the way until her full breasts rested on my upper thighs. Reaching up with her arms, she began lightly clawing my chest with her long nails, drawing them down over my side and belly, and continuing across my fully tented briefs - the "tent pole" quivering in anticipation. She continued down my inner thighs to my knees, raising goose bumps all along the way as she went. She returned to my briefs - using one hand she gently grasped my ball sack through the thin, cotton material; with the other she used the heel of her palm to massage the sensitive underside of my dick. I felt the pleasure of her touch course through me, the heat of my blood spreading deeply in my groin.

"Oh god, that feels so good Katherine, I moaned as she returned to the base of the shaft and started working her way up again. I could feel the wetness of my pre-cum oozing out, soaking the front of my briefs as she went. I started to jerk my hips, pressing up against her hand, trying to hump it. She knew I was getting close and would explode shortly if she continued. She would not allow it - not yet. There was so much more to do.

She moved her hands away from my crotch and began gently massaging my thighs to slow me down. After a few moments I settled down, the feeling of approaching orgasm passing as she ran her hands along my legs, squeezing and kneading the flesh as she went. After a while, her hands started to move up, massaging my hips, remaining clear of my crotch, working her way back up to my ribs and chest. She leaned forward and massaged my chest, squeezing and kneading the muscular flesh, running her thumbs over my sensitive nipples. As she worked her hands, her breasts bounced and swayed as if they had a life of their own.

Katherine leaned over further and brought her prominent lips to my nipples, encircling them with her tongue before pressing her lips tightly around and sucking them. As she did so, I felt her belly graze my crotch and I reacted by thrusting up against it. I looked down and saw her lush mane of wavy, dark brown hair cover my chest and tickle it as she continued to lick and suck my nipples. Glancing up I saw our reflections in the mirrored wardrobe across from the foot of the bed, her slim body writhing on mine as she licked and sucked her way down my chest.

She was sliding down my body as she licked, until she got to my swollen briefs. Katherine paused for moment before slipping her fingers under my waistband and slowly drawing them off me, sliding them down my legs and then free of my ankles. Lightly she grasped my quivering shaft with one hand as she bent low to taste the sensitive spot where the base of the shaft met the top of the scrotum. She used just the tip of her tongue, probing and licking, before using the flat of her tongue on my entire ball sack. I was in heaven, transported by the touch and sight, sound and smell of it all.

As Katherine worked her way up from my ball sack to the shaft, my rational, safety conscious persona, "Kelly B," reappeared briefly, picking up a condom packet and offering it to Katherine. She didn't look surprised or offended. In arranging the session, I had told her that I was completely phobic about sexually transmitted diseases and wanted us both covered at all times in both oral and anal play. This was a hard limit with me. Although the risk from uncovered oral play is considered to be small, it just wasn't worth the risk.

She opened the condom package easily, removed the latex ring and slipped it on top of my dick head, unrolling it over the glans and down the shaft. Her grip felt so food. I moaned in pleasure as the latex sheath made its way to the base. Quickly, Katherine bent low, took the base of my shaft in hand, formed her lips into an inviting "O" and lowered her warm, moist mouth over the head of my shaft. I felt the heat of her tongue press against the head, then swirl around the swollen glans. An almost electric jolt of pleasure coursed through my groin and spread outward until my entire body tingled with pleasure and anticipation.

Katherine must have felt my reaction since she repeated the move, this time pulsing the base of shaft with her gripping fingers and then swirling her tongue all round the head before slowing running the flat of her tongue down the underside of my shaft. She smiled as she saw the impact she was having on me - as I thrashed about, climbing the orgasmic peak. My body was wound tightly, tensed, ready to release. One or two more repeats of that technique and I would have gone over the top. Sensing how close I was, Katherine backed off, releasing my dick. I groaned almost frantic to release but also appreciating the effect of the tease.

Katherine straightened back up, still straddling my knees and began to put on a show for me, playing with herself. She brought her fingers to her mouth, wetting them, before pinching her own nipples, then kneading her breasts, pushing them out, presenting them to me. She brought one hand down to her swollen crotch, her panties bulging with her stiff member, and rubbed it, sliding her hand up and down, her shaft clearly visible in outline through the thin panty material, the head and glans peeking out over the waistband.

My eyes were glued to her, ranging up and down her figure taking everything in. I couldn't imagine a more erotic, arousing scene. Still straddling me, she slowly slid up my legs, over my hips to my belly and paused, wriggling slowly, squeezing her breasts and rubbing her swollen mound - putting on a show. It certainly worked. My eyes were glued to her, taking in every curve, every erotic movement.

Katherine inched up further until she was straddling my chest, knees snugly buried under my armpits as the show continued. My hands went to her ribs and slid up slowly, feeling every inch of her soft skin before coming to rest on her full breasts. Her nipples were very swollen, thimble sized and incredibly hard. She moaned as I massaged her, lightly grazing her nipples with my palms which elicited a tight squeezed of her thighs against the sides of my chest in response. Raising up slightly on her knees, she leaned forward bringing her swollen crotch to my chin.

Katherine brought her hands down on top of the headboard and leaned on it as she slowly gyrated her hips, grinding her crotch on my chin. I dropped my chin and found her swollen black panty covered crotch on my lips. It felt very hot and very alive - pulsing and jerking as she moved. I felt her hand brush my cheek as she slid it down to her crotch. She was looking down at me, deeply into my eyes when she drew the front of her panty across with her fingers to erveal her equipment.

It was starling to suddenly see a cock and balls looming over my face. It was completely shaven - bald, and looked enormous, especially this close up. The shaft stood fiercely erect at a forty-five degree angle, the head large, mushroom shaped and dark pink; the shaft was darker - a light tan and purplish hue that narrowed behind the head but then thickened noticeably as it went until near the base where it seemed to suddenly widen substantially. The image of a tree flashed across my mind - foliage, thickening trunk and wide base.

Of more immediate concern was Katherine's sack of balls which now dangled just an inch or so over my lips. It was darker, more purplish than the shaft and wrinkled, the deep ridges visible all around it. The sack was loose, the balls hung low and swayed slightly as she moved, balanced as she was on her knees with one hand resting on the headboard. It had a fresh, clean smell with just a hint of a citrus scent - perhaps the body wash she used. Katherine continued to look down at me, eyes locked onto mine, a corners of her mouth curved up a bit as a slight smile crossed her face.

"Lick me - let me feel your tongue," she said in a hoarse whisper, as she lowered herself a bit more, offering herself to me.

I was so aroused at that point, so completely under her spell that I probably would have done almost anything she told me to do. But even as excited as I was, I was aware that this was another moment of truth - really the last exit on this highway so to speak before I was committed to completing the voyage across the gender boundary. I don't remember giving any more thought than that as my lips seemed to part of their own accord and the tip of my tongue slid out reaching upward for her. She met me halfway, lowering herself a bit more until the tip of my tongue met the bottom of her scrotum.

It felt smooth, soft, almost velvety to my tongue as it touched and probed and finally licked the underside. It felt very much like shaven labia lips - perhaps less moist but very similar in texture. The thought occurred to me that this shouldn't be a surprise - that we all started out as females in the womb, the pre-birth labia lips of males closing under the influence of testosterone while in the womb to create the scrotum. We are all made of the same stuff - just arranged a little differently.

More importantly, I realized that the building didn't collapse on me, fire and brimstone didn't rain down and the earth didn't open and swallow me up. I was the same person after I "crossed the line" as I was before hand. It was as though I had lived these many years surrounded by what I thought were solid, immovable stone walls, only to discover that when finally tested, they turned out to be an illusion, no more than cleverly disguised tissue paper that gave way at the slightest push.

A soft moan escaped her lips as I licked upward along the scrotum seam, feeling the deep ridges of the sack. She lowered herself more and I opened wider, taking one ball gently in my mouth and swirling my tongue around it. I licked all around the ball sack covering it with my saliva until it shined in the dim light. Katherine then leaned forward as far as she could until her shaft rested on my face. It was incredibly hot and felt heavy, alive and pulsing as I laved her ball sack. Again, I was amazed at its size. It was considerably larger than mine, easily seven inches long and a good one and a half inches across, based upon my experience with variously sized strap-on dildos.

Report Story

bykelmag© 15 comments/ 255111 views/ 138 favorites

Share the love

Report a Bug

8 Pages:1234

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: