Heidi and Her GrandfatherChapter 6
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Heidi And The Prof free porn video
Heidi and The Prof
I'm Heidi, and I like to think of myself as a confident, outgoing
student here at Henley. I'm 19 and this is my second year here. Henley
is a small, private college in rural Pennsylvania specializing in
liberal arts, I'm studying English Literature and trying to fit in as
much extra-curricular activities as possible while getting decent
grades. Oh yeah, I was born male. I'm not sure if I'm transitioning or
what, but I identify as a woman, wear women's clothes and all the rest.
I take small doses of hormones but not really enough to have an ideal
body - I'm desperate to keep my penis the size it is (about eight to
nine inches when erect) and keep its function. Is that weird? Probably!
Sexuality-wise, I suppose I'm bi but generally prefer men. It's easier
for me to get women to sleep with me (which is another thing that is
weird), and purely gay guys aren't interested in sleeping with women,
even those like me with something more between their legs.
I'm about 5'8", 130 pounds with light red hair and freckles. I have a
round face and it's quite pretty when framed by my strawberry blonde
curls, even if I say so myself. I do a lot of sports (not much else to
do way out here, and it's a great way to meet people) so am quite fit,
plus I go to gym classes - spin bikes, boxercise, etc. I'm definitely
small upstairs but I've started using progesterone cream twice daily to
rub into my breasts. It's not supposed to affect my nether regions and
should increase size. Not sure if it works but it's definitely fun to
rub in!
Clothes-wise, I dress much more formally than most (if not all) the
other women at Henley. I like wearing dresses, usually with tights if
not proper stockings, high heels and tight skirts. I take care of my
backside and I think it's my best asset (aside from what's right in
front of it of course!) so like to show it off. I get some strange looks
from other women but the guys definitely seem to appreciate my dress
sense. Too many women come to classes in old sweatpants and T-shirts -
ugg! Why not show off what you have? I can even manage a passable
cleavage with the right bra.
Almost no one bothers me about being trans. I didn't think many people
knew but last year in the women's dorm I mentioned it to someone and the
next day everyone knew. I stay away from all the support groups and that
type of thing, I prefer not to make too big a deal about it. It's just
the way it is and if anyone doesn't like it, tough, just stay away and
let me be.
I've had some decent flings here. There was this one guy about a month
ago, thought I was a woman and had a bit of a surprise! But he handled
it well (so to speak...) we had a fun night and morning, but afterwards
he friendzoned me. I think he was a bit scared of somehow becoming
gay...! Seriously, but whatever, I'm sure he'll make someone a fine
husband one day, one who secretly watches gay porn. If it feels good and
doesn't hurt anyone...
But nothing since then. There are times when I'm so desperate I end up
talking to my toys. Then I edge myself for a couple of days and when my
balls are a deep shade of blue, I let myself go with my lover Edward (a
twisty, veined cock complete with balls, long and not too thick) jammed
up my rear, nipple clamps (well, clothespins really) and a ton of lube.
I've tried Fleshlights but my trusty hand full of oily goop works for
me. Along with Edward of course...a very demanding guy!
But this story is about me and Professor Cuthbert. John Cuthbert. He's
Head of English here at Henley and likes people to know it. A big man,
maybe 6'3 or so, solid but not heavy. Maybe about 55, grey hair and
pompous as hell. Typical prof at a small college, thinks that he's in
charge of the place and enjoys ordering everyone around. Now, I don't
take shit from anyone so he and I didn't hit it off that well. It was
always, "Young lady, see here, I've been doing this for 30 years,
and..." blah blah blah. Blue-rinse wife, practically obese, swans around
campus in her massive Audi. So anyway I'm second year now so I figured
he'd get out of my hair and find someone else to bother. How wrong I
was.
He asked to see me in his "chambers" (pompous or what?) after lectures
one day. Fine, I thought, let him tell me off and patronize me for an
hour and then I can get on with my life. What I didn't expect was that
he'd try to hit on me. These days it's a rarity due to the sensitivities
of university life in general and the litigious nature of students in
particular. The bad publicity would be killer - it would be all over
social media in minutes.
And old Cuthbert was so awkward about it. Touching my hair, telling me
I'm pretty, how he could ensure that I had a "high passing mark" for
English Lit...he laid it on thick. So I decided I could stand up and
scream at him, immediately see the VP and put in a formal complaint.
Or...I looked at him again. Hmmm, I thought, I could play this idiot and
perhaps get off at the same time. I was idly wondering if he had a big
dick when apparently he had asked me something.
"So, Heidi, would you like to meet with me outside of these august halls
of learning, for perhaps some, uh, more intimate discourse?" Yuck! What
an old perv. And a plan started to form. I can be devious when provoked.
"Oh yes, Professor Cuthbert, that sounds great. When and where? I have a
room in a house I'm renting with a few other women but it might not be,
oh, private enough for proper tuition. Do you have somewhere in mind
where we could really get into the various issues which need
discussing?"
Cuthbert's eyes widened, he thought he'd hit the jackpot. "Well yes, my
dear. Come by my house this evening. We'll be alone, I guarantee it as
my dear wife is staying with her cousin for a few days. Shall we say
8:00?"
I did my best not to smirk. His whale of a wife is probably out trawling
for krill. "Perfect! See you then." I gave him a saucy wink and walked
out, making sure I wiggled my assets as I knew he was staring,
anticipating plowing into me tonight. This was going to be so easy...
I didn't need much to get ready, just a gym bag with my toys. I put on a
sexy little black dress with stockings, garters and heels and a white
pouch thong that showed off my package nicely. I wasn't one of those
girls who tucked, I liked to have it all hanging out, or gathered nicely
to taunt. Funnily that women appreciated these small touches more than
men, but I guess that was to be expected.
I had a light dinner with my housemates. Lovely women all but I didn't
want to let them into my secret, at least not yet. I just told them that
I had a date and to wish me luck. Gina gave me a funny look; we were
sort of friends with benefits and she had become a bit clingy for a
while but she's better now that she has a boyfriend. We still
occasionally get together, usually when drunk, but she's so loud that
it's embarrassing the next day. I need to buy a gag for her - hope I
remember before our next tryst.
I rang the bell on the large house in its own grounds and the Prof
answered immediately - he must have been waiting for me. Excellent, I
wanted him eager and hot to trot. I put out my hand for a welcoming
shake and he kissed it. Hmm, this should be easier than I had thought!
He offered me a drink and we went to his library. Aside from a few
bookcases stuffed full of old books there was a fireplace with a nice
fire going, two large sofas and several armchairs along with a wet bar.
I sat smack in the middle of one of the sofas and crossed my legs,
making sure to show a lot of thigh. Prof had a smile plastered on and
was wearing what he probably thought was debonair, but was just a clich?
1970's academic outfit complete with forest green sweater and leather
elbow patches. He quickly brought the drinks to the glass table in front
of the sofas, Scotch and soda - typical he didn't ask what I wanted. I
took a miniscule sip and looked over at him.
"This is so nice, John. I'm going to call you John tonight. You may call
me Heidi for now. Come, sit next to me. No, closer, don't be shy."
Cuthbert was flustered - he definitely wasn't used to having someone
else in charge. I could see the wheels in his head spinning - he was
desperate to tell me off, to take command of the situation as usual, but
was afraid of offending me in case his great piece of ass would walk
out. So he tried patronizing me.
"Yes, of course my dear Heidi. Whatever you're most comfortable with as
I'm only concerned with your wellbeing." I was starting to get annoyed
with his bullshit. He scooted over so that our legs were lightly
touching. I put down the awful drink, pulled his head in and gave him my
very best kiss. It was a scorcher. It starts off soft, just a gentle
brush of my lips, then with my tongue just ever so slightly poking out,
then I bite my victim's bottom lip and stretch it out a bit and have it
snap back. I tease, pull back, tease some more before finally going for
an all-out assault; a dental hygienist would be envious of how
thoroughly I cover the mouth. My tongue eventually fucks the victim's
mouth as I push my body hard against theirs. I've never had it fail but
then again it's not had a lot of use as I mainly let people seduce me.
Lazy? Perhaps, but I'm a woman and I like being seduced. Still, special
situations call for proactive measures, and old Johnny-boy didn't know
what hit him. He was expecting a young, na?ve undergrad to be in awe of
him. I almost felt sorry for him. Almost.
I pulled back and massaged his upper thigh. "Did you like that, John?
Did you like it when I plunged my tongue in you? Like to stick my tongue
in warm, wet holes, don't you?" I licked my lips and ensured that my
eyes told the story of my arousal. I had a thought - what if I couldn't
get hard for this idiot? But then I thought, it'll be his job to make
that happen...
"Y...yes, Heidi, I...wow! I had no idea that you, that..." John
spluttered. I cupped his balls through his pants. He squeaked!
"Are these for me, John? Do you have big, hanging balls tucked away in
there? I bet they're blue - you can't still be fucking your wife. Let's
see what you have, John. Pull down your pants. Show me." I licked my
lips lasciviously. I was really getting into this now, and felt myself
getting hard. Good - it was so much easier this way.
This was a big moment, a major turning point of the evening. He could
yell and scream, kick me out, any number of things but I was counting on
him thinking with his little head. Men were very predictable and I was
confident that he would go along with it. Still, you never know how
things will turn out.
I reached in and unbuckled his belt to get him started. That seemed to
break the spell and he stood up. I looked at him with doe-like eyes and
an innocent expression, blinking, just waiting for him. He quickly
decided that although things weren't working out as he had planned, sex
was still on the cards so he lowered his tweed trousers to reveal what I
expected - tighty-white undies. Disappointingly he didn't seem to be
erect but the night was young.
"Oh, lovely John! You have a great body. You must work out all the time.
Let me feel your muscles." I stood up and fondled his biceps (flappy and
loose of course), quickly shifting to his chest, lightly covered with a
smattering of hair. I pinched his nipples. He squeaked again - bingo!
"You have such a manly chest. And you're so responsive. Do you like
this, John? Have you ever had your girlfriends play with your nipples?
You know, men like it as well as women." I leaned in to suck on each
one, rubbing against his crotch area. At last, signs of life there! "Oh,
John, this turns me on so much..." I kept biting and sucking on his
nipples and started to fondle his balls through his underwear.
"Just as I thought, big balls for a big strong man. Is this nice, John?
Do you like it when I rub your balls? Is it nice?"
"Y...yes, Heidi, it's...oh, ooo, I..."
"I know, John, let's move somewhere more comfortable. Are we alone in
this big old house? Where's your bedroom? We can get kinky there. Do you
like being kinky, John? I want to know everything..."
We quickly gathered our stuff (my bag and his pants, basically) and went
upstairs to a massive bedroom. It was very girly, cushions everywhere
and flowery sheets and wallpaper. I sat on the edge of the bed, still
fully dressed. "Take off the rest of your clothes, John, but leave on
your underwear. For now." John hesitated. I got up and gathered my
things as if to leave.
"Yes, Heidi, don't go, of course!" John practically yelled. Good, I
needed him to understand the rules. He obeys or I walk. But I needed to
get him to beg me to stay.
He quickly stripped off his shoes and socks and stood nearly naked in
front of me. "Now, John, do you like my ass? I noticed you staring at it
earlier. What do you think?" I leaned over the bed and pulled my dress
up. I was wearing my white thong and he could see my full ass with the
white string between my cheeks. "Is that nice? Give it a kiss. Go ahead
John, you know you want to kiss my ass. You might not get another
chance, a very young girl in your own house in your bedroom, showing you
her bare ass. Kiss it!"
John broke off his open-mouthed stare and knelt down in front of me. He
tentatively kissed one cheek then another. "Oh, that's nice John, you
like making me feel good. Go ahead, keep kissing. Don't stop until I
tell you. And don't forget to kiss between my cheeks as well. You never
know, I might let you kiss something else if you're a good boy."
That was my hook. Get him to do my bidding willingly, get him addicted,
and reward him for good behavior. I was damned if I wouldn't get this
old fool drooling over me soon, promising me the world. Little did I
know that I would do too good a job...
He slobbered over my ass. He was surprisingly obedient at this stage in
that he didn't try to go too far down to get at my 'pussy' he thought
was awaiting his attentions. Just stuck with the task. I gave him a few
minutes (it wasn't unpleasant, after all), and then pushed him back.
"Good boy! I loved having your tongue on my ass. Now come up here with
me, you've earned it."
John practically leapt onto the bed and put his hands out to fondle me.
I slapped them down. "John! Is that anyway to treat a lady? You only
touch me when I say, if I say. Got it?" He nodded sheepishly. "Good
boy." I gave him a kiss as a reward, lots of tongue as a hint what he
could get by obeying me. "Now lie down on your tummy, there's a good
boy."
I started with his calves and slowly massaged up to his underwear, then
switched legs and worked downward. I got some oil from my bag and got my
hands good and greasy, working them into his upper thighs. "There, told
you there would be a reward. Is that nice, John? Do you like this?"
"Yes, Heidi, it's great, but, well, how about if I reciprocate and give
you some pleasure now?" Clearly he wanted to fuck me but didn't want to
force the issue.
"Oh John, this is giving me such pleasure, massaging your manly legs.
I'll just work up a bit higher now." I let my fingers roam beneath the
leg openings of his underwear, just a little. I let my thumbs brush
against his balls as well. He started squirming and I slapped his ass,
hard, twice. "Now lie still, John! Bad boys are punished. I won't tell
you again." He stopped immediately, having cried out when slapped. Both
of these were good signs.
I decided to speed up the process, just a bit. "I need to massage you
all over and don't want to get any oil on your lovely underwear so I'm
going to peel them off. Also, I don't want to ruin my dress so that's
coming off but no peaking!" I quickly pulled off his undies. His ass
wasn't too bad, truth be told, for an older man. Still quite firm.
Hmmm...possibilities. I took off my dress to leave my push-up bra and my
thong. I knew he wouldn't look and in any case soon it wouldn't be an
issue.
I poured some oil on his ass, including into his crack. I slowly kneaded
the two large globes. Not very hairy at all, quite firm. Hmmm...could be
fun, I thought. I started pushing into his crack with my thumbs. Now to
start the real fun.
"You love this, don't you, John? I can tell. Tell me, have you ever had
anyone massage your gorgeous ass?"
"Uh, no, I haven't but it's, wow, fantastic, it feels so good..."
"I know! Doesn't it turn you on? My greasy, oily fingers pressing into
you? It really turns me on, John. And you're hard as a rock, aren't you?
Your cock doesn't lie, let me check - oh yes, hard and throbbing." I
gave his erection a little squeeze and he moaned. "Lie still now John or
I stop. Good boy. So, John, tell me about your sex life. Do you do it
much? Such a big handsome man, you must have all the undergrads after
you."
"No, not really, and not, well, not in a very long time actually. I was
surprised you agreed to get together Heidi. And my marriage, well, it's
more or less for show." I bit my lip to tell him that I didn't agree to
his little blackmail plan and wasn't surprised that it didn't work on
others.
"You know, John, not many women would get into this type of thing,
putting their oily fingers on a man's rear end and massaging it like
this. It's more of a man thing. Did you ever do it with another man?
Maybe fool around when you were a boy with other boys? I know it happens
all the time. Maybe at prep school, in the dorms? Just a little innocent
fooling around, practicing kissing? Maybe looking at pictures of nude
women and jacking off together, did you ever do that? And watch your
friend jack off, rubbing his erection, staring at the photo of a large-
breasted model? I bet you watched him stroke his cock, licking your
lips, didn't you? Tell me John, I want to hear everything..." I kept
stroking his ass, pushing harder into his crack, working down to his
asshole. I put a bit more oil in his crack and worked it in.
"No! Of course not, I'm not gay!" he spluttered.
"Oh I know, you're married, and here you are with a beautiful young
woman in your bed, obviously you're not gay. But I want to hear about
your school days and your experimentation. Did you reach over and touch
his cock? Did he touch yours? It was thrilling, wasn't it, to have
another boy touch you there? Did you kiss him while he was touching your
cock?"
I started to tease his hole, running my fingers back and forth across
it, around it and lightly teased the entrance. With my other hand I
started to rub his balls. "Oh, that's so nice...yes, well, we did fool
around, everyone did you know, young boys all together, away from
home...we touched each other, kissed, you know, but we weren't gay..."
"Pull your knees up, John, put your rear up in the air, that's it, just
there." I could get to his balls now and gently take each in turn,
pulling down on his large sack. They were certainly big. I avoided his
cock, sticking straight out now. I couldn't help running my finger over
the tip though, just to hear him squeak again.
"I know you're not gay, don't worry John, it just turns me on to hear
about you and other boys. Or men? Did you fool around with other men
after? No, OK, I get it, just when you were a boy. So, did you suck each
other off? Did you take his penis in your mouth? Was it nice, a bit
salty, hard and throbbing but silky soft at the same time? Tell me, did
you let your boyfriend touch you here? Did he take you to bed and stick
his fingers in you, like this? Did you let him put his penis inside you?
Did he pump it in and out, like this, John? Did his balls slap against
yours as he fucked you, fucked your ass in your dorm room? Did you moan
and cry? Did you come with his cock inside you?"
I had two fingers in his ass, gently pushing in and out. I took them out
and pushed my middle finger in deep until I felt his prostate and gave
it a good poke. There was that squeak again! Bingo. I kept it up along
with the banter. John was more or less silent with respect to actual
words but kept up a long string of whimpering, moaning and squeaking.
I got my bag and took out Edward, and slowly pushed him in slowly. "Is
this nice, John? Did it feel like this when your boyfriend fucked you? I
bet it did. Let yourself enjoy it, John, there's only the two of us
here. It's our private time, John, I want to watch you get fucked by
this cock. Doesn't it feel good?" I pushed it in hard and left it there,
maneuvering around to John's face. I gave him a long, wet kiss. "Did you
suck him off as well, John? I bet his young cock was delicious. All hot
and hard, precum dripping out. Did you lick it up first, then slowly
suck it in? Did you, John? Did you play with his young balls until he
shot into your mouth? I'm sure you swallowed it all, didn't you, John?"
Poor old John was beside himself, trying to hump my dildo in his ass,
sweating profusely and staring at me intensely. "Suck." I pushed two
fingers in his mouth. He slobbered all over them. I pushed them in and
out of his mouth. "They're a cock, use your tongue." He twirled his
tongue around my fingers and sucked on them like a man dying of thirst.
I pulled them out and decided to move things on, given that I'd
completely won, he was mine. I kneeled in front of his face and he could
see my hard cock partially covered by the white pouch. I carefully
pulled it down and my cock sprung free. John just moaned. I leaned
forward and slapped his cheeks a few times. "Yes, John, look what I
have! A hard cock, just for you. You want to suck it, don't you, you
dirty boy? Just like in the dorms, you want to lick the come off the tip
and suck it in your mouth, taste it. Beg me."
"Please Heidi, I need it, I need, uh, I need your cock. Let me lick it,
stick it in my mouth, anywhere, I need your cock, please, I'll do
anything." They always offer to do 'anything' but it's never the case,
especially after they come. Still...I rubbed the head against his lips.
"Lick, boy. Lick my hard cock." He slobbered all over it. No need to
tease any longer, I thought, and slowly pushed it down his throat.
Predictably he gagged immediately. I held his head firm for a few
seconds then pulled out. "Breath through your nose. Try again." He was
better that time. I slowly developed a rhythm. He wasn't awful but could
use practice. "Now hold still while I fuck your face." I held his head
and slowly fucked him. I couldn't go too deep but it was still fun. "I'm
fucking your face now John. That makes you a cock-sucker. Guess what,
John - you're a fag. Queer. Is that so bad? Feels good, doesn't it? You
get to suck my cock, feel my dildo in your ass. Better than fucking some
frigid, frightened freshman, isn't it?" I went deep a few times and
withdrew.
"More, please, Heidi, oh fuck me, fuck my mouth, please. I'm a fag, yes,
queer, homosexual, I've always been, just been hiding it. Please fuck
me, please, I want your beautiful cock..." He was pathetic now. I moved
back to his rear and slammed the dildo in and out a few times.
"You like that, don't you, John? Let's see if you like the real thing."
I slowly took it out, lubed up my cock and put in the tip. Squeak! Love
that from John. I slapped his ass a few times and pushed hard to get the
head in. "Enough gentle play John, time to get real." I quickly rammed
it in and out, not too deep but enough. John screamed a bit and bunched
up the bedsheets in his fists. Ah, happy days! He slowly got used to it
however. "You like that, don't you, you fucking slut? You little gay
boy? You like me fucking your big ass, slamming into you, slapping my
balls against yours, don't you? You fucking cock whore, let's pick it
up." I started slamming in hard, deep and fast. I could last a long time
and decided to give him a bit of a workout. I hoped he didn't have a
heart attack but was willing to take the chance.
After about 25 minutes I decided to finish. I held his greasy hips and
really went to town, hard as I could, slamming into him. He was
exclaiming on each downstroke now, something unintelligible. I finally
felt ready to let go and at the last minute decided to give him a bit of
a show. I was nearly there and pulled out, moved to the front and jacked
off all over his face. It had been awhile so I thoroughly coated him. It
took me longer than usual to recover, and I thought that I needed to hit
the gym more often.
John was stunned, in the exact same position. I scooped some of my cum
off his face and fed it to him. "Good boy, eat my cum. Lick it all up."
He eagerly licked it off my fingers. Definitely been broken. Still, I
wasn't all cruel, I wouldn't leave him without a little release.
"Turn over fag, show me your cock." He rolled over, his cock sticking
straight out. I thought he might have come from being fucked but no such
luck. Oh well, it wasn't all bad...
I put my ass down on his chest, facing his feet, and raised it up. "Lick
my ass, fag. Get your tongue in my hole." I lowered down and he held my
globes while licking my hole. He was better at rimming than cock-
sucking. Really good, got deep inside, lots of saliva, really went to
town. Very nice. I slowly lowered myself to his cock. It wasn't bad,
maybe six or seven inches and quite thick. My hands were still greasy
and I grabbed his balls with one hand and jerked him with the other. He
squeaked again and humped his hips up to fuck my fist. I let him and he
quickly started to spasm and then came in great globs, I caught it all
in my hands. When he was completely done I reached back and smeared it
on my ass. "Lick it off, dirty boy, clean all your cum off my ass. Suck
it all up." I was aware that he might not be in such a compliant mood
after having come but he was still in a trance-like subspace and he
immediately compiled, sucking and licking up all his cum from my ass.
I was done here. I gave him a little kiss and got my stuff together.
"Thank you for a lovely evening Professor Cuthbert. It won't be repeated
but don't forget about my grades, now will you?"
He just lay there like a beached whale as I walked out.
This should be the end of my story but alas, it's not. Starting the very
next day, I found that I has acquired my very own shadow. The professor
followed me around and pestered me like mad. I was his heroin and he was
jonesing for a fix. It didn't help his career, that's for sure, openly
pursuing a young undergrad around the campus.
I sort of took pity on him and let him suck my cock a few times, usually
in the ladies' room in the library. It amused me to see him on his knees
in a cubicle desperately sucking my cock, hearing giggles from the women
using the toilet.
Finally I tired of it and took him to a gay bar near to the largest town
where plenty of men cruised for rough trade. He quickly got picked up by
a large mean-looking guy with plenty of tattoos. I saw him the following
week looking much the worse for wear.
He's still here, still Head of English Lit. Lucky he has tenure. His
wife moved out, taking whatever money he had. He's quite a flamboyant
gay man now, openly flaunting his newly-discovered sexuality. If
anything, he's tolerated much more now than before. All thanks to me!
As for me, well, I found a lovely little twink who appreciates my
assets. He's fun, a bit shy and has a perfect ass. Boy are my housemates
jealous. Life is good!
Marisol
- 27.04.2020
- 19
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