Long sex story 8211 I Was A Reluctant Shemale
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Grandma’s Story – Wild Party free porn video
Jeff, arriving home from school, found Isabel napping on the couch in
the Family Room. Without waking her, he sat down to open the mail in
the large over-stuffed chair nearby, affording him a view of his
Grandmother’s thighs and the entrapped panties in the narrow crease
between the opulent twin mounds of her bottom. She was facing the back
of the couch with one leg pulled up and her short skirt hiked up over
her hips. The position enhanced the beautiful curve of her hips so
golden under the sheer -to- the- waist pantyhose molding her so
invitingly. Jeff sat quietly enjoying the view, remembering the warmth
that was his when he snuggled up to those generous buttocks in the
middle of the occasional nights they spent comforting each other
erotically. “It’s been, let’s see, four times in the past couple of
months — counting the experience when Auntie Ell had joined them in
bed for an unbelievable menage et trois.
Jeff was having a terrible time controlling himself in this process of
education his Gram and her girlfriend had embarked upon. Taken together
with the erotic content of his Psych class on the subject, he was
spending most of his waking hours and quite a few of his sleeping hours
in a serious state of arousal. He had discovered the meaning of
Nirvana!
He had a storehouse of experiments that needed to be tried out in their
“laboratory” sessions. The trouble was, that the girls seemed to have
more ideas of their own. Isabel stirred and moved her legs again,
stretching and showing a broader expanse of panty than before.
“Ahem!” Jef muttered, and then again, a little louder: “Gram!”
“Oh, my, hello Jeff honey, ready for dinner, eh? I better get going.’
She stretched and turned toward him, exposing her crotch, the center
seam of the pantyhose emphasizing the crease and pulling her panties
deep into the line of her pussy lips. “Oh, sorry, sweet heart, I’m all
exposed!” She laughed and pulled her legs neatly around and put her
feet together on the floor. She slipped into the high-heeled pumps
waiting by the front of the couch and stood up, shaking her skirt into
place. “there, that’s better, isn’t it?” she smiled and bent to kiss
his cheek..
“Uh …… no, not really,” he grinned, returning her kiss.
“Hey, hey, calm down!!” she joked and poked his shoulder. “You could
turn a girls’ head! —— “Oh, by the way, El wants to know if we can
kidnap you to be our chaperone us on an adventure she has in mind?”
“Yeessssss?” he asked, quizzically.
(AdProvider = window.AdProvider || []).push({"serve": {}});“She read an article in a magazine about a sexy Artists’ Costume Ball in
San Francisco and wants to go ……… but she’s afraid to go alone
……. So, want to chaperone us two for a little fun? By the way, Ell
has enough airline miles for three tickets.” Isabel stood smiling at
him across the kitchen island expectantly.
“Really? ……….. uh …. Well, ……. I don’t know much ….uh,
……about that sort of …… thing. How much help will I be?”
“Oh, Jeffy, we’ll think of something, I’m sure!! So …. Now, what do
you say?”
His sexy grandma smiled sexily and pulled her skirt up ’til he could
just see the crotch of her panties again and wriggled seductively.
“Ellen told me to see if my new panties from our shopping spree would
entice you, what do you think?”
“Sure, sure, of course, I’m just not sure you wouldn’t have more fun
without me!”, Jeff protested weakly, not wanting to be left out, really.
So, on Thursday they were off, sitting three abreast on a plane heading
for San Francisco. Jeff was in the middle with his totally out of
control partners in crime teasing him from both sides. After finishing
their limit of drinks, they had flirted shamelessly and successfully,
with neighboring traveling businessmen for a few more. There may be a
little gray in their hair, but they certainly had no trouble getting
male attention. Jeff thought as they settled down at last and asked for
blankets and pillows.
Covered in the blankets, Jeff felt Aunt Ell’s hand slide into his lap
from his left bringing him quickly to an aroused state. She smiled at
him and then pulled his hand into her lap. He could feel the warmth of
her thigh through the nylon of her stocking. He spread his hand,
enjoying the feel of the nylon stretched taut across her thigh. She
squeezed his hand between her thighs and smiled again into his eyes, as
she pulled his hand firmly higher, sliding her skirt before him.
Jeff thought about the pleasure it would be to spread her legs and
nuzzle against the sweetness of her panty crotch. Holding his hand
against her pussy, Ellen closed her eyes contentedly and fell asleep, a
smile still on her face and the taste of the last Grande Marnier on her
lips.
They were staying at the Westin and the girls excitedly planned shopping
for their sexy costumes the next day, including Jeff as part of the
excursion. ‘Me? I can’t go into those places with you? I’d never
stop blushing!” Jeff protested.
Nevertheless, the next morning they insisted and Jeff found wandering
with them into the nearby Frederick’s of Hollywood store, feeling
terribly out of place and certain that his face was crimson, as the two
woman held up sexy undies for him to pass judgement on.
They were having a good time already, and the sales girls had begun to
get into the swing of their laughter at Jeff’s discomfort.
“We have to start with a good foundation, Isabel, how about this bra for
starters? It’s called a “shelf”, Ellen was holding up a lacy
construction that looked like something was missing. “And how about
this one. Can I try this on?”
the salesgirl pointed to the fitting room.
“Come back in a minute, Jeff we need your advice,” she leered.
Jeff stood outside the fitting area, trying to look insignificant. Both
of them appeared through doors cracked open for him to see. Isabel’s
ample breasts were lifted and rounded spectacularly by “The Shelf”, her
nipples grandly exposed. Jeff’ felt his cock stirring ….. rising to a
strong erection. Isabel motioned him closer with a smile.
“What do you think, sweetheart?’
“I like it, I like it, ILIKE IT!!” Jeff was starting to warm to the
shopping fun!
“And how about this one for me, Jeff?” He turned to see Ellen, bare to
the waist with her lovely breasts lifted invitingly by a bra whose cups
were open to expose about 60% of her breasts, while lifting them with
the portion which ran under her breasts at the base of the pear like
tits. She lifted them with both hands, letting them settle into place
in the restraint of the bra and watching Jeff’s eyes bugging out at the
sight of her. The bra had little blue flowers as decorative points
between her breasts and also where the shoulder straps strained to hold
their cargo up. She took his hand and pulled in to touch the puckered
nipples which responded to his touch.
“This is a good start, Isabel, you look great! Now what effect do we go
for with our tush. I think one of those dresses that show your cheeks
would be good for you!!!!”
Isabel feigned shock.
“Oh my god, I don’t think I could do that in public ……. Could I?”
She looked at Jeff for answer.
“Well, you’ll look great no matter what, Gram! So I guess you could.
It’s strangers, anyway”.
“Hey, you two, look at this one! Ellen called from her dressing room.
They peered in to find Ellen in something which cinched in her waist and
had suspender straps for stockings. Jeff’s eyes were distracted by the
sheer see through panties she was wearing today.
“Oh, yeah, Aunt El, nice, he mumbled distractedly. I got to get out of
here,” he said, I’ll see you back at the hotel.”
They both laughed good naturedly, the two sales girls joining in as he
hurried out the door into the fresh air.
“Whew,” he sighed with relief.
The party was a wild thing. Colorful decorations, loud music and people
dressed to expose their bodies, their genitals, their breasts,
everything and anything was in view someplace in the room. Isabel wore
a dress with a cutout exposing the upper cheeks of her ass down to the
cleft between her buns and Jeff watched as a stranger dancing with her
let his hand stray across the exposed wonder, pushing through the cutout
area. Finally his hand was centered on her ass with his middle finger
stoking the top of her cleft. Jeff had trouble with his emotions
watching someone else enjoying his Grandmother’s soft treasures until he
was distracted by a girl with huge breasts capped by sequined nipples
and body paint -seemingly her only costume – asking him to lick some
cream off her nipple. He was happy to share it with her.
Jeff didn’t know how much chaperoning he should be doing, but the girls
seemed to be doing all right without getting completely raped and
carried off. They kept returning to him and getting rid of the latest
accoster of their curves. They were having a great time.
Ellen was wearing the non bra as a top, that is, no blouse, just the bra
exposing her breasts and a jacket which provided a little bit of
modesty, but not much. Wanting to know what those other guys were
feeling, he invited her to dance and spent the next twenty minutes
dancing slowly with her no matter what the music was, just feeling the
sensuality of her swaying breasts against him, the nipples tracing an
intricate pattern against his chest. Isabel’s hand tickled the back of
his neck and he felt her softness pressing against his thigh as she
straddled his leg, pressing the mound of her pussy against him. Her
hand found it’s way between them and fondled his cock as she whispered
in his ear.
“I can’t wait to get back to the hotel, Jeff. This is fun, but
…………. …….. I want to watch you stare at me with that hungry
look and then make wild passionate love to me!”
The last few words were delivered breathilly into his ear, making him
melt slightly and press her to him. His hand slipped down the back of
her skirt to find the firmness of a girdle, the first time he had known
either of them to wear one. He was looking forward to the experience of
undressing her.
Isabel tapped his shoulder and said. “Hey, Ellen, don’t forget we’re
sharing! How about swapping partners and let me dance with my handsome
grandson?”
Ellen spun off with a new partner and Isabel slipped into his arms
easily and pressed her softness against him. Her perfume welled up into
his nostrils from the warm space between her breasts, now lifted and
exposed by “the Shelf” bra under the tight dress with its low scooped
neckline. Jeff looked longingly at them from above her. She smiled up
at him and said ” Having fun, Jeff?”
“Sure, how about you, Gram.”
“Yes, this was a lot of fun. A once in a lifetime experience, I
guess.” Then she leaned closer and whispered into his ear. “I’m really
ready to go back to the hotel, though, if we can get Ellen back down to
earth. I’m afraid you are going to be awfully busy all night,
sweetheart. I think we both are going to want you to make love to us.
……… Did you eat your Wheaties, this morning.
She leaned back in his arms and looked at him with her head back and a
smile on her bright red lipstick coated lips, glistening invitingly.
Jeff reached to kiss them, tasting the lipstick as her tongue slipped
between his lips, fencing with his tongue. Jeff could feel her mound
pressed tightly against the bulge of his cock.
“Oooo, hon, ……. That feels ….so ….nice!!!!”
They arrived back at the hotel at about 2AM, making a bit of a scene as
they hurried through the sedate lobby. The two girls pressed against
him in the elevator and kissed him on both cheeks, rubbing themselves
against the length of his youthful body. “thanks, Jeffy, for the nice
night, they chorused into his ears.”
“OK, Ok, OK,” he grinned, “you two are a hell of a date, but you
attract a ot of attention!”
“We’ve only started, my dear, wait until we get you upstairs!”
Jeff had such a hard-on that he had trouble relaxing enough to urinate,
and he couldn’t get the vision of these two and their spectacular bras
out of his mind. Finally, he managed to be ready to great their eager
exhibitionism. Isabel was just taking off her dress to expose what had
been giving her a cleavage to the rear as well as to the front. A
Frederick’s special girdle with push up pads and an open section over
the cleft of her ass. She bulged throughout the opening spectacularly!
Her stockings clipped to the girdle’s tabs, their dark brown tops
contrasted beautifully with the white of her thighs. They were the real
old fashioned or – I guess they are called Full-fashioned, because of
the way they used to be made back in the old days. They were still the
sexiest things Jeff had ever seen, seeming to fit elegantly and to
inviting his kisses to linger up the columns of her legs, seeking the
warm wetness of her pussy. He longed to get started with the journey!
Ellen had thrown all the covers off one of the two king sized beds and
lay there in her girdle, stockings, heels and that showplace of a bra
pressing her tits out toward him like a gift. Ellen crooked her finger
and beckoned him closer. As Jeff came closer, she spread her legs,
inviting him with the view of the dark bands of her stocking tops to
slip between her thighs. He knew the wonderful sensual feel they would
give to her thighs as he pressed his lips close to her pussy. She
reached down quickly to unsnap a removable crotch panel and flung it
across the room, leaving him staring wide eyed at the gray streaked
auburn curls of her pussy. The curls glistened with the welcoming
juices of her pussy.
Jeff’s hands stoked up the sleek nylons and his tongue found it’s way to
her waiting pussy. “Ohhhhhh, …….Jeff,…… oooo..” he heard her
moan as his tongue parted the curls and found the juicy slit . He
pressed his tongue into the wet, slick valley of her pussy lips and
found her clitoris pricked up to meet his tongue. His hands found her
breasts and began caressing, squeezing them, loving them — loving the
feel of them in his hands. The scent of her perfume and of her pussy
juices mingled in his nostrils, trapped along with their warmth by the
taut band of her girdle now spanning from one thigh to the other and
cutting into the bridge of his nose as he pressed deeper, trying to
reach into her cunt with his tongue.
Jeff felt the bed move as Isabel joined them, pressing her nyloned legs
against his and reaching between his legs to squeeze his balls as he
licked and sucked on Ellen’s pussy. “Jeff, she began quietly, we bought
something else for tonight. ……. Something you mentioned from your
Psychology class …. ?’
Jeff nodded against Ellen’s sweet cunt as she held his head tightly in
place.
Isabel continued. ” we think it would be fun for you to ….. you know
…….. know what it is like when you ………. When you put your cock
into us and begin thrusting ………………….” She paused.
Jeff was startled, remembering mentioning the dildo and harness that had
been described in the class. He wasn’t sure he was enthusiastic about
the idea. Ellen said, “shhhhhh, Jeffy, keep it up …..ooohh, that’s
it.”
Isabel, had her hand under him and was squeezing his cock. She
continued, “So we decided that Ellen should be the one ……… if it’s
OK with you …………to take your virginity” she waited for him to
answer.
Ellen let him up for a moment. He looked up at her and she nodded to
him. We have a plan, Jeff, what do you think?” With some reluctance,
he gulped and mumbled, “uh, ….. yeah, I guess …….so…., yes,
yes.”
Ellen disappeared and Jeff turned to his Grandmother. She pulled him
toward her big breasts, offering them for him to suckle. Her nylons
felt delicious against his skin and his hands roamed over the exposed
voluptuousness of her tits as he sucked her large nipples between his
lips.
“Mnnnn, bite them, hon, …….. bite them a little ……. Just a
little …mmmmmmm. I like that, Jeffy.” His cock was against her
waiting thighs and Isabel helped him strip off the tight girdle, leaving
red marks on her ass, which Jeff kissed enthusiastically. Something was
appealing about the redness, must be what people get excited about
spanking, he thought.
Isabel spread her legs for him and guided his eager young hardness
toward the heat and moisture of her pussy, just as Ellen came back into
the room/. They both stared at her. She wore a smooth leather harness
around her waist and between her thighs, she had changed to a garter
belt so she still had her stockings on, but a large black rubber penis
protruded straight out from her pubic mound, mounted in the harness. It
looked huge to Jeff.
“wow, I don’t …..know …” he muttered with some concern.
That’s what you look like to us, sweetie, when you get so hard ,……
it looks like it would never be able to squeeze into us…….. you
know? It will be ok, she whispered soothingly, just relax.”
Ellen was spreading lots of K-Y jelly on her huge penis, rubbing it with
some relish, he thought. Jeff felt his cock pulled into Isabel’s loving
and eagerly waiting pussy. They struggled to push a pillow under her
hips, raising the angle of her vagina to enjoy him. He felt Ellen ‘s
small hand squeeze his ass and then his balls, feeling for his shaft,
now burying itself deep into Isabel’s cunt. Her finger invaded his anus
and he jumped at the feel of it.
She slowed and he felt the cold slickness of the lubricating jelly being
wiped around his hole and then felt her again slip one finger into him,
bringing the cold crčam with it. The thrill of it, coupled with the
sensation of Isabel’s gently milking pussy muscles, was electric
………. and he squeezed Isabel to signal her to wait or he would
immediately shoot off into her with all his hot juices.
They were both soothing him with their caresses, getting him ready to
accept this ritual defloration
Ellen positioned herself behind him and he felt the bluntness of the
cock rubbed up and down his crack, then centering at the opening of his
ass. “Ready? Ellen whispered hoarsely, obviously choked with the
surprising excitement of this new act. She pressed gently against his
tight sphincter and he tensed. Then he felt himself relax at the
soothing feel of the lubricant. She was able to press the knob of the
head of the penis into his anus, the muscle clamping over the head of
it. He felt the burning sensation of being spread so wide, then a more
soothing feeling as Ellen slowly pressed into him.
Jeff excitedly pressed into Isabel and began thrusting against her
gentle and firm counter thrust and her loving caress of his cock with
her vagina. Jeff buried his face in her breasts as she hugged him close
and thrust up and down on his cock with strong movement of her hips on
the pillow.
Ellen was now thrusting in and out of him, adding her thrust to his
penetration of his lovely Grandmother’s pussy. He felt the strangeness
of the huge penis deep inside the tunnel of his asshole, felt the
strange pleasure of it along with the stimulation of his genitals and
that organ he couldn’t remember the name of but was supposed to be a
problem when you got older.
He didn’t have time to think about it as the three of them strained
against each other, working together to pleasure each other.
Jeff felt the nylons and satiny garments of the two girls heightening
his pleasure, felt the heat of their breasts, Isabel’s hot pussy and
clasping vaginal muscles surrounding him, milking him, pleasuring him.
Ellen was stroking into him with hard thrusts and he watched in the
mirror as her tits bounced up and down with her extreme exertion. He
felt his balls strain and then shoot their creamy contents spurting into
Isabel.. it was the strongest he had ever felt, as spurt after spurt
traveled the length of his cock and splashed against her pussy walls.
He felt Isabel squeeze him to her body in orgasm and heard her sigh in
his ear; “ohhhh, yes,’ …………oh baby, …….do it, baby cum in
me……slam it into me …..hard, har, …..hard …errr, harder.
That’s it, yes…….oh your cum feels good, sweetheart.
They all crumpled together, feeling the sweat of their exertions and the
juices of their pleasure mingling as they calmed each other with caress
after caress, lying quietly, feeling each other, the girls rubbing their
nylons against Jeff and playing with his balls and now softening cock.
Jeff alternated between suckling Isabel’s long nipples and nibbling on
Ellen’s slightly smaller but still lovely breasts.
“Three happy campers,” Ellen giggled.
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