Lee47
TMF Regular
- Joined
- Apr 12, 2013
- Messages
- 166
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I had occasion to go talk to my boss in her office the other day at the prison where we work. I should explain that my boss is probably 5 or 10 years older than me, a beautiful platinum blonde who is about 6'3" in heels, has long legs, a slender torso, and firm, medium-size breasts. (Lest you think I'm stalking my boss, she dresses in low-cut clinging blouses and tight skirts which do not hide any of her assets, and she pats me on the back quite frequently and literally; we have a very happy, mutually flirty relationship.) While chatting with her, the following fantasy inexplicably came into my mind....
Roxanne (my boss) has called me in to tell me that our prison system is about to switch over to housing all females, and that all the male officers have to undergo a series of physical tests to make sure that, if we were taken hostage by woman prisoners, we would be able to hold out under duress.
She calls in her secretary, Shelley, a younger, buxom brunette. Shelley locks the door and closes the drapes on the windows. Roxanne sits down and leans back in her chair, crossing her long legs. She instructs me to sit down on her desk. I sit down, a little nervously, noticing that everything has been cleared off the top of the desk. I can feel Shelley standing right behind me. She is breathing heavily.
Roxanne orders me to take my uniform shirt off.
"What?!" I ask, shocked.
"Take the shirt off," Roxanne says sternly, leaning forward. "I'm not telling you again."
Unnerved, I slowly unbutton my shirt, glancing from Roxanne to Shelley, trying to figure out what's going on. When I finally get my shirt off, Shelley takes it from me.
"T-shirt too," Roxanne orders.
I take off my T-shirt and hand it to Shelley, then sit topless on the desk, sweating a little, as Roxanne eyes my bare chest and stomach. I can feel Shelley's presence behind me as a warmth on my back. I am starting to get aroused.
"Okay, Shelley, let's start testing," says Roxanne. "Slow at first. Lee, the idea is for you not to make a sound. Remember; no matter what happens, don't make a sound."
Suddenly Shelley's fingers skitter down my back, like spiders, from the nape of my neck to the small of my back. I can't believe it- my boss' secretary is tickling me!! I give out an involuntary giggle as her soft fingertips graze over my skin.
"Oh, dear, Lee," says Roxanne, shaking her head sadly. "That's not very good. She barely touched you. Would you like to try again? Your job is on the line, after all..."
"Yes," I answer, startled by the idea that I could be losing my job over something like this. "I was just surprised. I can do better."
Shelley's fingers start tickling my neck again, lightly, brushing gently downward. I cringe as she tickles down my spine and over my shoulder blades, using light, spider-like motions. My shoulders jerk and twitch as I struggle to hold in my laughter. Roxanne watches in obvious enjoyment as Shelley's fingers dance lower and lower. Now she's approaching the small of my back, causing me to shudder. Roxanne is giggling sympathetically at my plight, making it harder and harder for me to resist giggling along with her as Shelley's fingers spider-walk towards my belt...
Then I explode with helpless laughter as Shelley unexpectedly digs her fingers into my ribs, poking and prodding mercilessly as I shudder and shake. I have never been tickled like this before! The only one to come close was my grad-school lover, Christa, who would tickle-torture me in bed while teasing me, chanting, "Tickle, tickle, tickle!!" At the thought of her, combined with Shelley's relentless tickling, my cock starts swelling in my pants.
After endless minutes of rib-tickling, Shelley's fingers probe up my sides into my hairy armpits. She starts scratching with her sharp nails, making me laugh so hard it's painful. Her fingers alternate deep digging with light spider-dancing, unpredictably, deviously, making it impossible for me to predict what she's going to do next. I try to clamp my arms to my side, but Roxanne unfolds her long, sexy legs and stands in front of me, siezes my wrists, and stretches my arms over my head. Now I am helpless and completely exposed to Shelley's tickling. Her wicked fingers are now able to tease from my waist up to my wrists. She climbs onto the desk for better access, so I can feel her soft breasts in her silky blouse pressed against my back. With Roxanne's cleavage in front of me at eye level, I am surrounded by beautiful womanly flesh. Between tits and tickling I am going crazy! Shelley is tickling me everywhere from the waist up, reaching around to poke at my navel, tweaking my nipples in between tickles; and all the while my erection is throbbing in my pants.
Roxanne and Shelley lay me down on my back across the desk. Roxanne produces some lined leather restraints from somewhere in the desk and secures my wrists, while Shelley straddles my waist, tickling my underarms with her evil fingernails. Roxanne then goes down to my feet, and I feel her tugging my shoes and socks off. Suddenly, I can feel fingers on the soles of my feet! I start laughing even harder as Roxanne scribbles her fingernails from my heels, up to my toes, then to my arches!!! I can't stand it and start begging for mercy as these women tickle me crazy!!
Roxanne and Shelley are giggling and laughing along with me as they tickle, comparing notes on my most ticklish spots. I barely notice it in my agony, but Shelley has unbuttoned her blouse exposing a lacy bra, and her skin is covered with a fine sheen of sweat. Once in a while she sneaks a hand up to caress her breasts or pinch a nipple, in between tickling and tweaking mine. When Shelley briefly moves position, I can see that Roxanne has taken her blouse and skirt off and is wearing only a beige bra, matching panties, and high heels as she kneels on my legs, holding my bare feet captive as she merclessly tickles them. Besides tickling my soles and arches, Roxanne also tickles in between my toes, which I have never experienced before. Each time she squirms her slender fingers between my toes, it makes me howl and thrash so that she and Shelley are almost thrown off of me.
Shelley is tirelessly tickling every inch of my upper body. She has moved down to straddle my pelvis so she has full access to my torso; as a result, she is riding on top of my aching cock. She is clearly enjoying how turned on the tickling has made me, and grinds her crotch against mine as I squirm helplessly. She loosens my belt and pants so she can tickle down to the waistband of my undershorts, mercilessly teasing the sensitive skin, fluttering her fingertips just above my hairy mound. I am unbearably turned on by her teasing fingers, so close to my straining erection yet refusing to touch it... then Shelley laughs wickedly and tickles my armpits and ribs again.
Roxanne stops tickling my feet, and I feel a moment of relief; but then she tells Shelley to lift up so she can get my pants off! Roxanne tugs my trousers down and off my legs, leaving me naked except for boxers. Shelley sits on me again; with her tickling me I can't even think of trying to throw her off. Roxanne starts tickling between my thighs and behind my knees, her fingertips like tiny spiders on my skin. Worse, every tickling touch is making me hornier and hornier.
Shelley, riding my crotch, can feel every twitch and throb of my cock as they mercilessly tickle-torture me. She is also getting more and more turned on. While Roxanne tickles my feet and legs, Shelley strips, revealing her large, pale breasts and shaved pussy; then she begins slowly, voluptuously rubbing her pussy and clit against my cock, through the fabric of my shorts, grinding her clit against me until she brings herself to orgasm.
The tickling stops while Shelley catches her breath and Roxanne takes off her lingerie. I am too exhausted to do anything but pant and giggle, even when Roxanne peels my shorts off and straps my ankles to the desk, then leans over me, her heavy breasts pressing against my chest.
"Lee, so far you've failed this test miserably. If you were subjected to this kind of torture, you would break immediately. I'll give you one last chance; Shelley is going to tickle your balls while I tickle your cock. If you can keep yourself from cumming, you pass the test. But we're not going to make it easy on you. And you really want to cum, don't you?" she whispers, trailing a fingertip lightly along my quivering penis.
I whimper as Shelley brings a fingertip to the base of my scrotum and traces it from side to side, lightly, teasing, tickling... but I must try not to react. Roxanne smirks as she watches my face; she can tell how much I need release. She is running her fingertip around the head of my cock, tickling so lightly and teasingly that every nerve in my groin is on fire... and she is doing this with just one finger. How will I be able to stand it when she starts really tickling?
Now Shelley is using one finger on each hand, slowly tickling each testicle in tiny circles, just barely brushing the skin, like ants crawling on my helpless balls; and Roxanne is lightly stroking the tips of her index fingers along the sides of my shaft, from the head to the base, lightly and teasingly, one stroke a second. I feel her breath tickle in my ear as she whispers, over and over, "Tickle, tickle, tickle. Tickle, tickle, tickle! Tickle, tickle, tickle!!!" My helpless cock twitches with every word; yet I tell myself not to cum, against every instinct and my overwhelming need...
My universe is now no bigger than this office. There is nothing but Roxanne and Shelley, their terrible tickling fingertips, my aching balls, and my swollen cock. I desperately need to cum; yet I can't let myself; but every touch of these wicked women is driving me closer to the edge. I have no sense of time passing, I am trapped in an eternity of tickling, measured by how many fingers are lovingly teasing my helpless cock and balls. Shelley slowly adds a fingertip at a time to those teasing my contracted balls, until four fingers are lightly tickling each helpless testicle, flicking over the skin, doing a gleeful, loving tickle-dance, while her thumbs tickle my perinium, making me moan with helpless desire; and her warm breath blows over my sensitive skin, adding to my torture. Roxanne is using both hands to lightly stroke my penis, her thumbs holding it still so that her evil fingertips can dance up and down from the crown to the root, flickering faster and faster. Never in my life have I been tickled for so long or so mercilessly; even Christa would have had mercy long ago and let me cum! My cock is throbbing in Roxanne's hands, it seems to be growing with her every touch, aching for release; yet I can't let myself cum....
"You want to, don't you..." Roxanne whispers in my ear. "You want to cum. You need to cum..." She licks my earlobe, sending shivers through my whole body. "You won't be able to hold out... against the tongue-tickle..."
Roxanne straddles my head, her wet **** in my face. I feel her hot breath on my throbbing organ as her fingertips tickle the sides of my shaft and Shelley tickles my balls even more rapidly; then the tip of Roxanne's tongue touches my glans, so lightly that it tickles, too. I can't control myself anymore and break out in screaming laughter. A moment later, Shelley's tongue goes to work on my balls, making a wet, wiggling, tickly path from my perinium up to the base of my cock, over and over.
But it is Roxanne's tongue that is driving me to the breaking point. "I must not cum" is turning into "I'm going to cum!!!!" Every swirling, tickling touch of her wet tongue drives me closer to orgasm, and I finally can't resist, no longer want to resist, and as the energies rise from the base of my balls up my cock I scream, not in agony this time but in pleasure. Roxanne seals her mouth over my cock and wraps her fingers around my shaft as my orgasm begins, milking my cock, sucking greedily as I cum screaming; then she lowers her wet pussy to my face so I can eat her until she has her own orgasm.
After I am given a few minutes to recover, Shelley and Roxanne play with my cock and balls until I am ready for more. Shelley rides me until we both cum, then Roxanne takes her turn; then I am released, and the three of us sit in Roxanne's big office chair, cuddling, kissing, and fondling.
"You may not be suitable for working with female prisoners," Roxanne tells me, "but I'd like to offer you a place on my... personal staff. And I have a habit of taking my work home with me."
Roxanne (my boss) has called me in to tell me that our prison system is about to switch over to housing all females, and that all the male officers have to undergo a series of physical tests to make sure that, if we were taken hostage by woman prisoners, we would be able to hold out under duress.
She calls in her secretary, Shelley, a younger, buxom brunette. Shelley locks the door and closes the drapes on the windows. Roxanne sits down and leans back in her chair, crossing her long legs. She instructs me to sit down on her desk. I sit down, a little nervously, noticing that everything has been cleared off the top of the desk. I can feel Shelley standing right behind me. She is breathing heavily.
Roxanne orders me to take my uniform shirt off.
"What?!" I ask, shocked.
"Take the shirt off," Roxanne says sternly, leaning forward. "I'm not telling you again."
Unnerved, I slowly unbutton my shirt, glancing from Roxanne to Shelley, trying to figure out what's going on. When I finally get my shirt off, Shelley takes it from me.
"T-shirt too," Roxanne orders.
I take off my T-shirt and hand it to Shelley, then sit topless on the desk, sweating a little, as Roxanne eyes my bare chest and stomach. I can feel Shelley's presence behind me as a warmth on my back. I am starting to get aroused.
"Okay, Shelley, let's start testing," says Roxanne. "Slow at first. Lee, the idea is for you not to make a sound. Remember; no matter what happens, don't make a sound."
Suddenly Shelley's fingers skitter down my back, like spiders, from the nape of my neck to the small of my back. I can't believe it- my boss' secretary is tickling me!! I give out an involuntary giggle as her soft fingertips graze over my skin.
"Oh, dear, Lee," says Roxanne, shaking her head sadly. "That's not very good. She barely touched you. Would you like to try again? Your job is on the line, after all..."
"Yes," I answer, startled by the idea that I could be losing my job over something like this. "I was just surprised. I can do better."
Shelley's fingers start tickling my neck again, lightly, brushing gently downward. I cringe as she tickles down my spine and over my shoulder blades, using light, spider-like motions. My shoulders jerk and twitch as I struggle to hold in my laughter. Roxanne watches in obvious enjoyment as Shelley's fingers dance lower and lower. Now she's approaching the small of my back, causing me to shudder. Roxanne is giggling sympathetically at my plight, making it harder and harder for me to resist giggling along with her as Shelley's fingers spider-walk towards my belt...
Then I explode with helpless laughter as Shelley unexpectedly digs her fingers into my ribs, poking and prodding mercilessly as I shudder and shake. I have never been tickled like this before! The only one to come close was my grad-school lover, Christa, who would tickle-torture me in bed while teasing me, chanting, "Tickle, tickle, tickle!!" At the thought of her, combined with Shelley's relentless tickling, my cock starts swelling in my pants.
After endless minutes of rib-tickling, Shelley's fingers probe up my sides into my hairy armpits. She starts scratching with her sharp nails, making me laugh so hard it's painful. Her fingers alternate deep digging with light spider-dancing, unpredictably, deviously, making it impossible for me to predict what she's going to do next. I try to clamp my arms to my side, but Roxanne unfolds her long, sexy legs and stands in front of me, siezes my wrists, and stretches my arms over my head. Now I am helpless and completely exposed to Shelley's tickling. Her wicked fingers are now able to tease from my waist up to my wrists. She climbs onto the desk for better access, so I can feel her soft breasts in her silky blouse pressed against my back. With Roxanne's cleavage in front of me at eye level, I am surrounded by beautiful womanly flesh. Between tits and tickling I am going crazy! Shelley is tickling me everywhere from the waist up, reaching around to poke at my navel, tweaking my nipples in between tickles; and all the while my erection is throbbing in my pants.
Roxanne and Shelley lay me down on my back across the desk. Roxanne produces some lined leather restraints from somewhere in the desk and secures my wrists, while Shelley straddles my waist, tickling my underarms with her evil fingernails. Roxanne then goes down to my feet, and I feel her tugging my shoes and socks off. Suddenly, I can feel fingers on the soles of my feet! I start laughing even harder as Roxanne scribbles her fingernails from my heels, up to my toes, then to my arches!!! I can't stand it and start begging for mercy as these women tickle me crazy!!
Roxanne and Shelley are giggling and laughing along with me as they tickle, comparing notes on my most ticklish spots. I barely notice it in my agony, but Shelley has unbuttoned her blouse exposing a lacy bra, and her skin is covered with a fine sheen of sweat. Once in a while she sneaks a hand up to caress her breasts or pinch a nipple, in between tickling and tweaking mine. When Shelley briefly moves position, I can see that Roxanne has taken her blouse and skirt off and is wearing only a beige bra, matching panties, and high heels as she kneels on my legs, holding my bare feet captive as she merclessly tickles them. Besides tickling my soles and arches, Roxanne also tickles in between my toes, which I have never experienced before. Each time she squirms her slender fingers between my toes, it makes me howl and thrash so that she and Shelley are almost thrown off of me.
Shelley is tirelessly tickling every inch of my upper body. She has moved down to straddle my pelvis so she has full access to my torso; as a result, she is riding on top of my aching cock. She is clearly enjoying how turned on the tickling has made me, and grinds her crotch against mine as I squirm helplessly. She loosens my belt and pants so she can tickle down to the waistband of my undershorts, mercilessly teasing the sensitive skin, fluttering her fingertips just above my hairy mound. I am unbearably turned on by her teasing fingers, so close to my straining erection yet refusing to touch it... then Shelley laughs wickedly and tickles my armpits and ribs again.
Roxanne stops tickling my feet, and I feel a moment of relief; but then she tells Shelley to lift up so she can get my pants off! Roxanne tugs my trousers down and off my legs, leaving me naked except for boxers. Shelley sits on me again; with her tickling me I can't even think of trying to throw her off. Roxanne starts tickling between my thighs and behind my knees, her fingertips like tiny spiders on my skin. Worse, every tickling touch is making me hornier and hornier.
Shelley, riding my crotch, can feel every twitch and throb of my cock as they mercilessly tickle-torture me. She is also getting more and more turned on. While Roxanne tickles my feet and legs, Shelley strips, revealing her large, pale breasts and shaved pussy; then she begins slowly, voluptuously rubbing her pussy and clit against my cock, through the fabric of my shorts, grinding her clit against me until she brings herself to orgasm.
The tickling stops while Shelley catches her breath and Roxanne takes off her lingerie. I am too exhausted to do anything but pant and giggle, even when Roxanne peels my shorts off and straps my ankles to the desk, then leans over me, her heavy breasts pressing against my chest.
"Lee, so far you've failed this test miserably. If you were subjected to this kind of torture, you would break immediately. I'll give you one last chance; Shelley is going to tickle your balls while I tickle your cock. If you can keep yourself from cumming, you pass the test. But we're not going to make it easy on you. And you really want to cum, don't you?" she whispers, trailing a fingertip lightly along my quivering penis.
I whimper as Shelley brings a fingertip to the base of my scrotum and traces it from side to side, lightly, teasing, tickling... but I must try not to react. Roxanne smirks as she watches my face; she can tell how much I need release. She is running her fingertip around the head of my cock, tickling so lightly and teasingly that every nerve in my groin is on fire... and she is doing this with just one finger. How will I be able to stand it when she starts really tickling?
Now Shelley is using one finger on each hand, slowly tickling each testicle in tiny circles, just barely brushing the skin, like ants crawling on my helpless balls; and Roxanne is lightly stroking the tips of her index fingers along the sides of my shaft, from the head to the base, lightly and teasingly, one stroke a second. I feel her breath tickle in my ear as she whispers, over and over, "Tickle, tickle, tickle. Tickle, tickle, tickle! Tickle, tickle, tickle!!!" My helpless cock twitches with every word; yet I tell myself not to cum, against every instinct and my overwhelming need...
My universe is now no bigger than this office. There is nothing but Roxanne and Shelley, their terrible tickling fingertips, my aching balls, and my swollen cock. I desperately need to cum; yet I can't let myself; but every touch of these wicked women is driving me closer to the edge. I have no sense of time passing, I am trapped in an eternity of tickling, measured by how many fingers are lovingly teasing my helpless cock and balls. Shelley slowly adds a fingertip at a time to those teasing my contracted balls, until four fingers are lightly tickling each helpless testicle, flicking over the skin, doing a gleeful, loving tickle-dance, while her thumbs tickle my perinium, making me moan with helpless desire; and her warm breath blows over my sensitive skin, adding to my torture. Roxanne is using both hands to lightly stroke my penis, her thumbs holding it still so that her evil fingertips can dance up and down from the crown to the root, flickering faster and faster. Never in my life have I been tickled for so long or so mercilessly; even Christa would have had mercy long ago and let me cum! My cock is throbbing in Roxanne's hands, it seems to be growing with her every touch, aching for release; yet I can't let myself cum....
"You want to, don't you..." Roxanne whispers in my ear. "You want to cum. You need to cum..." She licks my earlobe, sending shivers through my whole body. "You won't be able to hold out... against the tongue-tickle..."
Roxanne straddles my head, her wet **** in my face. I feel her hot breath on my throbbing organ as her fingertips tickle the sides of my shaft and Shelley tickles my balls even more rapidly; then the tip of Roxanne's tongue touches my glans, so lightly that it tickles, too. I can't control myself anymore and break out in screaming laughter. A moment later, Shelley's tongue goes to work on my balls, making a wet, wiggling, tickly path from my perinium up to the base of my cock, over and over.
But it is Roxanne's tongue that is driving me to the breaking point. "I must not cum" is turning into "I'm going to cum!!!!" Every swirling, tickling touch of her wet tongue drives me closer to orgasm, and I finally can't resist, no longer want to resist, and as the energies rise from the base of my balls up my cock I scream, not in agony this time but in pleasure. Roxanne seals her mouth over my cock and wraps her fingers around my shaft as my orgasm begins, milking my cock, sucking greedily as I cum screaming; then she lowers her wet pussy to my face so I can eat her until she has her own orgasm.
After I am given a few minutes to recover, Shelley and Roxanne play with my cock and balls until I am ready for more. Shelley rides me until we both cum, then Roxanne takes her turn; then I am released, and the three of us sit in Roxanne's big office chair, cuddling, kissing, and fondling.
"You may not be suitable for working with female prisoners," Roxanne tells me, "but I'd like to offer you a place on my... personal staff. And I have a habit of taking my work home with me."
