A first for me (a F/M story)
Tommy Jordan had just turned 18, graduated from high school and was ready to leave home and head off to college. He enjoyed his life at home but was ready for the challenges that college would bring.
Of course, he knew there would be some that would tease him. He was a handsome fellow with wavy brown hair and dark blue eyes, but he only stood about 5’2” and he had such a baby-face that many thought him to be 13 instead of 18. He never excelled at any sport and yet had a toned, slim body.
On this hot summer day, Tommy was getting ready to enjoy his favorite pastime; sneaking into Ms. Walters backyard and ogling her while she sunbathed ! Ms. Regina Walters was a buxom 35 year old who Tommy had always had fantasies about. The svelte redhead towered over him at 6'3” and had an amazing figure that would make any young man swell with lust ! Just thinking of her made his shorts rise a little in response.
It was easy to sneak into Ms. Walters backyard. She had a wooden fence that surrounded it completely, but there was one spot where you could slither through if you were skinny enough. There was just enough dirt dug out of a small hole so that you could lay on your back, put your arms above your head, and wriggle your way through without getting scratched by the rough wood.
He was careful as he squirmed down into the hole not to rip his t-shirt on the rough edges of the wood and pushed with his tennis shoes to slide him through. Quietly, he crept towards a row of bushes that bordered Ms. Walters pool. This was his favorite hiding spot and offered him an unobstructed view of the chair she usually laid down on.
Peeking past the bushes, he gasped in delight as he saw her laying out for his enjoyment! She was wearing one of her famous string bikinis; a bright yellow one. Her full breasts were barely contained by the garment and he could see them rise and fall with each breath she took. Her lovely pink size 7 soles were pointed right at him and he felt himself rise as he gazed upon her beauty.
He was so caught up in drinking in all of her loveliness, that he almost didn’t see the snake that slithered quickly away from him ! He recoiled in shock and fell against the bush he was hiding behind !
Regina’s green eyes shot wide open at the sound ! “Tommy Jordan ! Is that you peeping at me again !” she said with mock severity !
“Oh shit ! Busted !” Tommy thought. “I’d better get the hell out of here !” As quickly and as silently as he could, Tommy worked his way back to the fence. If she didn’t catch him, she couldn’t be sure it was he !
“Made it !” he thought as he raised his arms over his head and began to slither back through the hole by the bottom of the fence. He had just got his head and shoulders on the other side when he felt a massive weight plop down on his stomach !
“My my !” Regina cooed softly, “…what do we have here ?”
Tommy tried frantically to pull himself free with his arms and kick with his legs, but Ms. Walters’ full weight sat on his hips and he was quite firmly trapped !
“I wonder what the punishment should be for a naughty little Peeping Tommy ?” Regina thought out loud. “I’ll have to think on that.”
Tommy kept his mouth firmly shut ! She couldn’t see his face and he might yet be able to wriggle her off of his hips.
“HEEEEYEEEEEHAHAHAHAHAAAAAAAAAAA !!!!” he suddenly burst out with laughter !
Regina had both of her long-fingernailed hands at Tommy’s ribs and was vigorously tickling his sides ! “Tickle, tickle tickle !!” she sang.
Tommy hadn’t thought he was this ticklish, but trapped as he was, there was nothing he could about it ! He tried in his laughter to wriggle and buck the sexy red head off of him, but she had him pinned helplessly to the ground ! The longer she tickled him, the weaker he became until any chance of escape had been tickled right out of him ! Within minutes he was trying to grab whatever breath he could take between his shrieks of helpless laughter. And what made it worse was Ms. Walters had planted herself firmly atop his manhood which was beginning to grow larger as she tickled him ! In his mind he knew there was only the thin fabric of his shorts and the thinner fabric of her bikini bottoms that separated the two !
Regina had known for years that Tommy would sneak into her backyard when she was sunbathing and delighted in giving him little shows that she knew any young man would love ! She adored the short brown haired boy but never let on that she knew he was watching her. She enjoyed teasing him immensely and knew that one day, he would become a man. But now that he was an adult, she could tease him even more ! And apparently, her teasing was having an effect !
She tickled Tommy until he was hoarse with laughter and had no chance of slithering away from her ! With an evil grin, Regina grabbed his t-shirt and ripped it completely off! Now she had a bare, ticklish torso to play with !
Tommy watched through tear-blurred eyes as the remnants of his t-shirt came sailing over the fence ! That was the last thing his eyes beheld for a while as his captor began to wriggle her long nails up down his bare ribs !
“HEEEEEEEYAAAAAAHAHAHAHAAAAAAAA !!!” he bellowed as the tickling forced the laughter from his throat !
Regina continued to tickle Tommy until the sounds he made became a hoarse croaking imitation of real laughter. He had stopped flailing his arms and his legs jerked uselessly upon the soft grass. Knowing that she’d tickled him into hysterical helplessness, Regina began to consider other fun targets. She turned around until she faced his tennis shoes and with nimble fingers, began to untie them.
“HEYYYEEEEHEHEHEEEEEE !!!” He gasped, “WHAAAAAHAHAHAAAAA… WHAT ARE YOU DOOOOOHOHOOOOOOOING ???”
He felt her pull off his right shoe and start untying his left and he fearfully realized what was going to happen next !
“NOOOOOHOHOHOHOOOO !!!! C’MON… STAAAAHAHAHAAAAAAAP !”
Regina pulled off his other shoe and like its mate, tossed it over the fence into Tommy’s back yard. Tommy saw his tennis shoes plunk down onto the grass and then exploded with laughter !
“YEEEEEEEEEEEEHAAAAAAAAAAAAAAAHAHAHAHAAAAAAAAA !!!!”
Regina was raking her long nails up and down the soles of Tommy’s trapped bare feet ! She was amazed at how small and soft they were for a young man, almost as soft as a woman's, then remembered that Tommy wasn’t an athletic type and spent most of his time on his studies. With great relish she tickled and teased his wriggling bare feet until once again, he was sobbing and gasping desperately for breath ! Regina was growing excited from tickling her young neighbor but was getting even more aroused by the feeling of his swelling manhood that pushed and rubbed against her barely covered mound ! Tommy may have been short and slim, but there was definitely one part of him that was neither short nor slim !
Tommy’s mind was in a whirl ! Any idea of escape was lost to this turmoil and all that existed was the unbearable tickling and the delicious feeling of something wonderful rubbing against his growing bulge ! He couldn't believe his bare feet could be THIS ticklish, but indeed they were ! The only effort he expended was that which was needed to gulp as much air as he could into his oxygen starved lungs !
The more Regina tickled Tommy’s bare feet, the more aroused he became ! Regina was shamelessly rubbing herself against Tommy as she felt him grow harder and harder by the minute ! Regina had definite plans for this ticklish young man's tender bare feet, but for right now, she had other wicked plans in mind !
She tickled Tommy into utter helplessness, barely able to grab a breath when she turned around and started unbuckling his shorts ! Peeling them down, she gasped with delight at the incredibly long, hard manhood she had just unveiled ! Tommy may have been thin and short but MY GOD ! This young man was hugely endowed !
Tommy's eyes were clenched shut as he writhed helplessly from Regina’s wicked foot tickling ! He didn't see his shorts and briefs come sailing over the fence, but he realized he'd been stripped completely nude when he felt the redhead's sopping wet mound gliding sensuously up and down his raging hard on ! Despite his helplessly weak condition, he knew that it wouldn't take long for him to explode with delight ! That is, until Regina began to count his clearly defined ribs !
Once again Tommy squealed as the tall redhead tickled him senseless ! Rational thought rapidly departed Tommy's brain. Any thought of orgasm was gone as he desperately tried to breathe !
Regina could not control her lust any longer ! She peeled aside her skimpy bikini bottoms and greedily stuffed Tommy's hardness deep within her ! Her eyes rolled back into her head as she felt the delirious joy of this young man's rock hard manhood sliding deeper and deeper within her ! She buried herself atop her little tickle-toy and sobbed with unabashed delight ! Not wanting to spend him too quickly, she redoubled her efforts at tickling Tommy's tummy and ribs !
Tommy cackled insanely and bucked furiously against the sexy redhead ! Each violent upward thrust was met with an equally violent hip grind as Regina used her little tickle toy like an animated vibrator ! She knew he wouldn't be able to cum while she tickled him senseless but she was free to mount towards an explosive orgasm !
Having finally lapsed into silent laughter, the quivering Tommy could only buck and slam ferociously into his redheaded captor ! Regina gasped with erotic delight and began to shudder and writhe helplessly as her own orgasm seized control of her body ! Despite the feelings that wracked her muscles, she never stopped tickling Tommy's ribs, leaving the young man completely helpless and unable to achieve his own bliss !
After 5 delicious minutes of heaven, Regina finally shuddered to a halt while Tommy was only minutes from passing out from lack of oxygen ! Reluctantly, she extricated herself and gazed lovingly at the sobbing, barely breathing nude young man before her. With malicious intent, she slid her naked tickle toy from under the fence and easily slung his limp body over her shoulder. She had been waiting for this day for a long time and she was fully prepared ! She giggled with delight as the one part of Tommy's body that wasn't limp poked and prodded her firm breasts as she carried him !
Tommy Jordan had just turned 18, graduated from high school and was ready to leave home and head off to college. He enjoyed his life at home but was ready for the challenges that college would bring.
Of course, he knew there would be some that would tease him. He was a handsome fellow with wavy brown hair and dark blue eyes, but he only stood about 5’2” and he had such a baby-face that many thought him to be 13 instead of 18. He never excelled at any sport and yet had a toned, slim body.
On this hot summer day, Tommy was getting ready to enjoy his favorite pastime; sneaking into Ms. Walters backyard and ogling her while she sunbathed ! Ms. Regina Walters was a buxom 35 year old who Tommy had always had fantasies about. The svelte redhead towered over him at 6'3” and had an amazing figure that would make any young man swell with lust ! Just thinking of her made his shorts rise a little in response.
It was easy to sneak into Ms. Walters backyard. She had a wooden fence that surrounded it completely, but there was one spot where you could slither through if you were skinny enough. There was just enough dirt dug out of a small hole so that you could lay on your back, put your arms above your head, and wriggle your way through without getting scratched by the rough wood.
He was careful as he squirmed down into the hole not to rip his t-shirt on the rough edges of the wood and pushed with his tennis shoes to slide him through. Quietly, he crept towards a row of bushes that bordered Ms. Walters pool. This was his favorite hiding spot and offered him an unobstructed view of the chair she usually laid down on.
Peeking past the bushes, he gasped in delight as he saw her laying out for his enjoyment! She was wearing one of her famous string bikinis; a bright yellow one. Her full breasts were barely contained by the garment and he could see them rise and fall with each breath she took. Her lovely pink size 7 soles were pointed right at him and he felt himself rise as he gazed upon her beauty.
He was so caught up in drinking in all of her loveliness, that he almost didn’t see the snake that slithered quickly away from him ! He recoiled in shock and fell against the bush he was hiding behind !
Regina’s green eyes shot wide open at the sound ! “Tommy Jordan ! Is that you peeping at me again !” she said with mock severity !
“Oh shit ! Busted !” Tommy thought. “I’d better get the hell out of here !” As quickly and as silently as he could, Tommy worked his way back to the fence. If she didn’t catch him, she couldn’t be sure it was he !
“Made it !” he thought as he raised his arms over his head and began to slither back through the hole by the bottom of the fence. He had just got his head and shoulders on the other side when he felt a massive weight plop down on his stomach !
“My my !” Regina cooed softly, “…what do we have here ?”
Tommy tried frantically to pull himself free with his arms and kick with his legs, but Ms. Walters’ full weight sat on his hips and he was quite firmly trapped !
“I wonder what the punishment should be for a naughty little Peeping Tommy ?” Regina thought out loud. “I’ll have to think on that.”
Tommy kept his mouth firmly shut ! She couldn’t see his face and he might yet be able to wriggle her off of his hips.
“HEEEEYEEEEEHAHAHAHAHAAAAAAAAAAA !!!!” he suddenly burst out with laughter !
Regina had both of her long-fingernailed hands at Tommy’s ribs and was vigorously tickling his sides ! “Tickle, tickle tickle !!” she sang.
Tommy hadn’t thought he was this ticklish, but trapped as he was, there was nothing he could about it ! He tried in his laughter to wriggle and buck the sexy red head off of him, but she had him pinned helplessly to the ground ! The longer she tickled him, the weaker he became until any chance of escape had been tickled right out of him ! Within minutes he was trying to grab whatever breath he could take between his shrieks of helpless laughter. And what made it worse was Ms. Walters had planted herself firmly atop his manhood which was beginning to grow larger as she tickled him ! In his mind he knew there was only the thin fabric of his shorts and the thinner fabric of her bikini bottoms that separated the two !
Regina had known for years that Tommy would sneak into her backyard when she was sunbathing and delighted in giving him little shows that she knew any young man would love ! She adored the short brown haired boy but never let on that she knew he was watching her. She enjoyed teasing him immensely and knew that one day, he would become a man. But now that he was an adult, she could tease him even more ! And apparently, her teasing was having an effect !
She tickled Tommy until he was hoarse with laughter and had no chance of slithering away from her ! With an evil grin, Regina grabbed his t-shirt and ripped it completely off! Now she had a bare, ticklish torso to play with !
Tommy watched through tear-blurred eyes as the remnants of his t-shirt came sailing over the fence ! That was the last thing his eyes beheld for a while as his captor began to wriggle her long nails up down his bare ribs !
“HEEEEEEEYAAAAAAHAHAHAHAAAAAAAA !!!” he bellowed as the tickling forced the laughter from his throat !
Regina continued to tickle Tommy until the sounds he made became a hoarse croaking imitation of real laughter. He had stopped flailing his arms and his legs jerked uselessly upon the soft grass. Knowing that she’d tickled him into hysterical helplessness, Regina began to consider other fun targets. She turned around until she faced his tennis shoes and with nimble fingers, began to untie them.
“HEYYYEEEEHEHEHEEEEEE !!!” He gasped, “WHAAAAAHAHAHAAAAA… WHAT ARE YOU DOOOOOHOHOOOOOOOING ???”
He felt her pull off his right shoe and start untying his left and he fearfully realized what was going to happen next !
“NOOOOOHOHOHOHOOOO !!!! C’MON… STAAAAHAHAHAAAAAAAP !”
Regina pulled off his other shoe and like its mate, tossed it over the fence into Tommy’s back yard. Tommy saw his tennis shoes plunk down onto the grass and then exploded with laughter !
“YEEEEEEEEEEEEHAAAAAAAAAAAAAAAHAHAHAHAAAAAAAAA !!!!”
Regina was raking her long nails up and down the soles of Tommy’s trapped bare feet ! She was amazed at how small and soft they were for a young man, almost as soft as a woman's, then remembered that Tommy wasn’t an athletic type and spent most of his time on his studies. With great relish she tickled and teased his wriggling bare feet until once again, he was sobbing and gasping desperately for breath ! Regina was growing excited from tickling her young neighbor but was getting even more aroused by the feeling of his swelling manhood that pushed and rubbed against her barely covered mound ! Tommy may have been short and slim, but there was definitely one part of him that was neither short nor slim !
Tommy’s mind was in a whirl ! Any idea of escape was lost to this turmoil and all that existed was the unbearable tickling and the delicious feeling of something wonderful rubbing against his growing bulge ! He couldn't believe his bare feet could be THIS ticklish, but indeed they were ! The only effort he expended was that which was needed to gulp as much air as he could into his oxygen starved lungs !
The more Regina tickled Tommy’s bare feet, the more aroused he became ! Regina was shamelessly rubbing herself against Tommy as she felt him grow harder and harder by the minute ! Regina had definite plans for this ticklish young man's tender bare feet, but for right now, she had other wicked plans in mind !
She tickled Tommy into utter helplessness, barely able to grab a breath when she turned around and started unbuckling his shorts ! Peeling them down, she gasped with delight at the incredibly long, hard manhood she had just unveiled ! Tommy may have been thin and short but MY GOD ! This young man was hugely endowed !
Tommy's eyes were clenched shut as he writhed helplessly from Regina’s wicked foot tickling ! He didn't see his shorts and briefs come sailing over the fence, but he realized he'd been stripped completely nude when he felt the redhead's sopping wet mound gliding sensuously up and down his raging hard on ! Despite his helplessly weak condition, he knew that it wouldn't take long for him to explode with delight ! That is, until Regina began to count his clearly defined ribs !
Once again Tommy squealed as the tall redhead tickled him senseless ! Rational thought rapidly departed Tommy's brain. Any thought of orgasm was gone as he desperately tried to breathe !
Regina could not control her lust any longer ! She peeled aside her skimpy bikini bottoms and greedily stuffed Tommy's hardness deep within her ! Her eyes rolled back into her head as she felt the delirious joy of this young man's rock hard manhood sliding deeper and deeper within her ! She buried herself atop her little tickle-toy and sobbed with unabashed delight ! Not wanting to spend him too quickly, she redoubled her efforts at tickling Tommy's tummy and ribs !
Tommy cackled insanely and bucked furiously against the sexy redhead ! Each violent upward thrust was met with an equally violent hip grind as Regina used her little tickle toy like an animated vibrator ! She knew he wouldn't be able to cum while she tickled him senseless but she was free to mount towards an explosive orgasm !
Having finally lapsed into silent laughter, the quivering Tommy could only buck and slam ferociously into his redheaded captor ! Regina gasped with erotic delight and began to shudder and writhe helplessly as her own orgasm seized control of her body ! Despite the feelings that wracked her muscles, she never stopped tickling Tommy's ribs, leaving the young man completely helpless and unable to achieve his own bliss !
After 5 delicious minutes of heaven, Regina finally shuddered to a halt while Tommy was only minutes from passing out from lack of oxygen ! Reluctantly, she extricated herself and gazed lovingly at the sobbing, barely breathing nude young man before her. With malicious intent, she slid her naked tickle toy from under the fence and easily slung his limp body over her shoulder. She had been waiting for this day for a long time and she was fully prepared ! She giggled with delight as the one part of Tommy's body that wasn't limp poked and prodded her firm breasts as she carried him !
