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My College Adventures – 5 
by Netman169 (netman169@yahoo.com)

***

My name is Jake Trenton. I am in my fifties now. This is 
the story of my sex life while at college. Part 5 
describes my first bondage experience, which happened 
when Miss Witherspoon, a French Literature Teaching 
Assistant, tutored me. (MF, mast, oral, bd, tor)

***

Chapter 5: The BD Teaching Assistant – Opening New 
Horizons

During my sophomore year, I was having some trouble in 
my French Literature class. Try as I might, I just 
didn’t understand writers like Voltaire. It was a large 
lecture class and there were a number of TA’s (Teaching 
Assistants) to help those of us having trouble. 

I signed up for a help session and waited to be 
contacted. I got a call later. It was from Miss 
Witherspoon, one of the TA’s. She said all of her office 
times were booked so she added some evening sessions at 
her apartment. I booked an 8:00pm slot for the next 
night and tried catching up on my notes and reading.

I arrived on time the next night, book and notes in 
hand. Miss Witherspoon met me at the door and let me in. 
She was twenty-one years old and a grad student at the 
university. She was one of the more attractive TA’s. She 
was tall, had long, straight black hair, and a dynamite 
body. Her breasts were solid 36 D’s. Her look and attire 
was always on the edgy side. Tonight was no different. 

She was dressed in a short black leather skirt, a black 
silk blouse, black silk stockings, and black high-heeled 
shoes. I didn’t know how I could ever concentrate with 
her looking like this but I managed to try. 

We powered through the material and I was finally 
starting to understand the French writer/philosopher. 

When we finished, she asked if I wanted some wine to 
celebrate my understanding. I accepted and she uncorked 
a bottle of red and handed me a glass. Taking a glass 
herself, she joined me on the couch.

As she sat, her skirt rode way up her legs and I got a 
good look at the milky white thighs above the tops of 
her stockings. As we talked, she didn’t seem concerned 
at how she was sitting. 

She asked me who was my favorite French writer and I 
admitted I really didn’t have one. She handed me a book 
from her coffee table and asked if I ever read it? It 
was the Illustrated Works of Marquis de Sade. Of course 
I had heard of him but really didn’t know a lot. 

Thumbing through the book, there were numerous 
illustrations of men and women in various acts of 
bondage and torture.

“I don’t understand why people do this stuff.” I said. 
“Do they really get off on it?”

“They sure do!” she explained. “If you want I can show 
you? I’m done tutoring Literature for the night but I 
wouldn’t mind tutoring you in this.”

“I’m always willing to learn new things,” I said. “Where 
do we start?”

“Follow me into my dungeon, I mean bedroom,” she said.

She was right the first time - it was a dungeon! The 
walls, ceiling and even the floor were painted black.

In the middle of the room was a four-poster bed with 
leather straps attached to each post. There was a wooden 
rack against the wall with restraints strategically 
spaced to spread ones arms and legs. And throughout the 
room were a number of ropes, whips and weird looking sex 
toys. 

I wondered what had gotten myself into.

“Here, strip and change into this while I get ready,” 
she said handing me a pair of leather undershorts.

As I changed, she stripped out of everything but her 
high heel shoes and black, silk thigh-high stockings and 
stood before me naked. Her breasts were the biggest I 
ever saw in real life although her nipples were weren’t 
as long as Marilyn’s. Her pussy was shaved completely 
bare making her plush outer lips and slit quite visible. 
Her legs were long and smooth and her butt was perfectly 
round.

I felt myself starting to get a hard-on but the tight 
leather undershorts quickly restrained it.

“And one more thing,” she said, “We need a safe word. 
It’s the word we’ll use if we want to stop the activity 
– if it gets too intense or painful. How about 
Voltaire?”

“So now the only rules are that there are no rules. You 
can do anything you want to me using anything in the 
room. If you need any help or ideas, check the 
illustrations in the book. Restrain me, hurt me, and 
make me cry. Don’t stop unless I say the safe word,” she 
explained.

“I always like to start by being tied up,” she said. 
“But you can do whatever you want.”

Since I had no idea what to do, that sounded like a plan 
to me. I pushed her to the floor and grabbed some silk 
rope that was nearby. I remember seeing some western 
movies where the victims were “hog tied”.

I started by tying her hands behind her back then went 
up around her neck finishing by binding her ankles so 
that her legs were stretched backward almost touching 
her head. She started to scream so I placed some duct 
tape over her mouth.

With her in this vulnerable state, I decided to play 
with her naked body. I took some other rope, and started 
wrapping it tightly around her right tit. It squeezed it 
so tight it became long and thin and the nipple 
distended to about a full inch. I then did the same to 
the left one.

Taking another piece of rope, I knotted it and went down 
to her pussy. Before doing anything I took a long look. 
I never saw and adult woman’s hairless pussy, I only saw 
teen Nellie and Jane’s. I was fascinated how much 
plushier it seemed without any hair. After getting a 
good look, I inserted the rope over her slit with the 
knot right on her clitoris. I attached the other two 
ends to the first rope near her neck. As a result each 
time she squirmed and stretched, the knot would rub 
against her clitoris.

Now I just had to make her squirm. I started by spanking 
her round butt. As my hands started leaving red marks, 
she was thrashing all about. I could see the knot 
digging into her clit. I could tell she was having pain 
on her butt and pleasure at her clit. I wondered which 
one would prevail?

Turning Miss Witherspoon over, I remembered how 
distended her tits and nipples were. I started to slap 
her tits and nipples with a little horse crop I found. 
This tit slapping really caused her body flop around 
causing the knot to work more of its magic. 

Wanting to get her going even more, I looked around to 
see what else I could find. On the floor I discovered a 
ten-inch solid rubber dildo and some lube.

Lubing it up I got a real perverse idea. Rolling her 
back over I ran the dildo up and down her butt crack. I 
could hear her screaming in anticipation of what I might 
do. As I reached her anus I couldn’t help myself. I 
thrust the dildo into her ass hole and pumped it in and 
out. This caused her whole body to buck and contort, 
digging the knot tightly into her clit.

Her whole body shook in both pain and pleasure. I was 
beginning to understand just what this bondage was all 
about. 

Ripping the tape off and unbinding the ropes, I expected 
she might have been mad. On the contrary, she seemed 
pleased at how fast I had learned.

“Is that it?” she asked.

“Well I didn’t hear you say Voltaire so I’m not quite 
done with you yet, bitch!” I shouted playing my role.

I dragged her over to the rack on the wall, spread her 
arms and legs, and clamped them in place. She was 
dangling from the wall, restrained, naked and spread 
eagled before me. 

I covered her mouth using a classic rubber ball gag.

After warming up using the ropes, I was ready to get 
down to some serious torture. I again started with her 
tits. On the floor was a bucket of spring-type 
clothespins. Taking them one at a time I clipped them in 
a circle around each areola.

Then I placed my mouth on her nipples until they 
expanded and clipped another clothespin on each.

The normally pink nipples turned red and I could see 
some tears in Miss Witherspoon’s eyes but she wasn’t 
trying to yell anything through the gag.

Taking my hand, I flicked on the clothespins on her 
tits, making it even more uncomfortable.

Then I turned my attention to her plush, shaved pussy. 
Grabbing hold of each outer vaginal lip I stretched them 
apart and down. Then I took two pussy clips and attached 
one to each lip. There was little hook on each for 
attaching weights.

I started attaching them one at a time. As I did, each 
of her outer labia lips stretched downward. When her 
lips stretched to twice their normal size I stopped 
adding weight.

In addition to stretching them down, the weights spread 
them apart exposing her clitoris. I tried to decide how 
I would handle that? 

First I took a special clip designed for use on the 
clit. It was made of soft rubber and the spring tension 
was not as strong. After rubbing her clit to make it 
expand, I attached the clip to the fleshy knob. Then I 
flicked it back and forth along with the clothespins. 
That did seem to be hurting her. 

After a while I took it off and looked for something 
else. I found a suction device that looked like it was 
designed to fit over a clitoris. Placing it over her 
love bud, I started to pump the bulb. As I did, it 
exerted pressure on her clitoris, causing it to expand. 
I pumped and pumped until it doubled it size. She was 
only reacting slightly so I continued pumping until it 
tripled. I was now getting the pleasure/pain reaction I 
was looking for.

When I took it off I saw that her clit was still triple 
size and I looked for something else. I came across a 
little cattle prod which shot electric sparks out the 
tip. Placing it an inch from her distended clit, I 
turned it on. 

I could tell she was screaming as I sent shocks into her 
clitoris.

Wishing to temper the pain with some pleasure, I found a 
twelve-inch mechanical vibrating dildo. It not only 
vibrated but the tip rotated in a circle, while the 
shaft pumped in and out.

Turning it on, I plunged it all the way into her wet, 
splayed open pussy hole.

This caused an immediate reaction. Her whole body 
started approaching an orgasm. Seeing this I zapped her 
clit causing the orgasm to subside. This seemed kind of 
fun, so I took the prod away and let the vibrator work 
its magic again. 

After a while, another orgasm started at which time I 
re-shocked her clit stopping the pleasure in its tracks. 
I did this five more times and could tell she was 
getting really agitated.
As another orgasm started, I again zapped her clit 
leaving her totally frustrated. 

Before she could start to cum again, I pulled out the 
vibrator and lay down the prod. I proceeded to take off 
the clothespins, weights, clamps, restraints, and gag. 
As I did she practically fell to the floor.

After a while she stood up. “My turn to do you now,” she 
said.

I wasn’t quite sure what she had in mind but decided to 
find out.

The first thing she did was bind me to the wooden rack 
spread-eagled and remove my leather undershorts. 
Surprisingly my cock was flaccid from being restrained 
in them. Before I could get hard, she slipped a metal 
chastity type belt on me. It fit snug around my waist 
yet was looser in the crotch area. When she put it on 
me, she showed me a group of sharp spikes in this crotch 
area, barely touching my flaccid cock.

I knew if I got even the slightest bit hard, my cock 
would press up against the spikes. Then Miss Witherspoon 
started her games. She lay in front of me spreading her 
legs and opening her pussy to my gaze. Her goal was to 
make me hard so my cock would encounter the spikes. My 
goal was not to let this happen.

She started by fingering her pussy. Seeing a girl do 
this in porn videos always made me hard so I didn’t 
think I had a chance seeing it live. I clenched my teeth 
and tensed up my whole body to try and keep from getting 
hard. 

When she saw I was succeeding, she stepped up the 
arousal by fisting herself. Even though that brought 
back memories of Marilyn, I still managed to keep from 
getting hard. 

Then she took a twelve inch flesh colored dildo and 
started pumping it in and out of her pussy. It looked 
like she was being fucked by a cock. She was so juicy, I 
could smell her arousal from six feet away. Yet 
miraculously, I managed to stay soft. 

I understood the game that she was playing with me. She 
pitted my mind against my body and luckily for my cock, 
my mind won.

“Very good,” she said removing the chastity device from 
me. “Let’s see how well you do with this next thing?” 

Taking a thin rope, Miss Witherspoon looped one end and 
slipped it over my cock just below the cockhead. Then 
she tugged the rope forward with one hand while making 
my cock hard with the other. As my cock expanded, she 
stretched it out to the limit and then secured the rope 
to the wall. Considering the amount the base pulled away 
from my pelvis, my eight-inches were stretched to at 
least ten.

Now I was facing the opposite problem from before. If my 
cock went soft, the pain of the constricting rope would 
be excruciating. I needed to remain hard no matter what 
she did.

She started by taking a page from what I did to her. 
Miss Witherspoon took some flexible weights and draped 
then one at a time over my shaft. They were putting 
tremendous pressure on my outstretched cock but I 
managed to remain hard by thinking of those little girls 
I got to see naked. 

After taking the weights off, she dripped hot chocolate 
all over it. After burning for a moment, it cooled down 
and actually had the opposite effect when she leaned 
down and licked my shaft clean.

Finally she placed her legs on each side of my 
outstretched cock and started to pee on it, thinking 
this would gross me out and make it go soft. Little did 
she know that recalling my experience with Nellie made 
me get even harder.  

After untying my cock, Miss Witherspoon had to think of 
some other way to torture me. With me still bound to the 
rack, she slid a cow-milking machine sheath over my 
cock. It is the device they use to milk cows with. It 
provides both suction and a milking action and the speed 
can be controlled. 

Feeling it suck and pump my cock I was relieved that I 
would finally get to cum. She started it off slow and 
steady. It was feeling really good. (No wonder farm boys 
are always so happy.)

Miss Witherspoon slowly increased the speed until she 
felt me ready to explode. But like I did to her, she 
shut the machine right before I could cum.

After letting me calm down a while, she started the 
machine once more. Soon I was on the verge on cumming 
again but just before I did, I felt the cattle prod 
zapping the base of my shaft. (I guess turnabout is fair 
play!) Needless to say, this really stemmed the tide of 
my ejaculation.

On the third time, she turned the machine on high. At 
that setting it didn’t take me long to feel the pressure 
building up in my balls again. “Surely she would have 
the decency to let me cum now,” I thought.

But just as I was again about to ejaculate, she dunked 
my balls into a bucket of ice water stopping my orgasm. 
This really broke my spirit and I yelled, “Voltaire!” 

Hearing this, she removed the milking machine and took 
me down from the rack.

I pretended to fall down limp, but after she totally 
unbound me I jumped up and grabbed her.

I dragged her to the bed and lay her down. Her body was 
still a mess from our earlier activities. Her tits were 
red and welted, her pussy lips were distended, and her 
clit was twice its size and looked sore. 

“Hey, no fair,” she yelled. “You said Voltaire!”

“Yes but you didn’t, bitch!” I exclaimed.

Using the leather restraints on the bedposts, I tied her 
spread eagled on her 
stomach with her butt sticking up in the air. It looked 
so round peering out above the thigh highs. She looked 
at me shocked yet still didn’t utter the safe word.

Noticing that I hadn’t worked on that butt in a while, I 
reached down and grabbed a cat o’ nine tails whip. I 
started hitting her butt and back. I went gently at 
first but detecting no response, I increased my 
whipping. I was hitting her so hard, red marks started 
to appear all over her ass and back. She was clearly 
responding now both breathing heavily and crying, yet 
she did not utter the safe word.

I untied her and turned her onto her back. I retied her 
spread-eagled and the front of her naked body was now 
totally exposed to me again. At this point I was ready 
to proceed with a more sexual punishment.

The first thing I went for were her tits. I placed 
little bites all around one of her D-cup mounds before 
landing my lips on her areola. I bit in a circle all 
around it and finally came to her nipple. It was still 
sticking out quite a bit and was easy to clamp my mouth 
onto. I sucked it hard into my mouth and then went to 
the other breast.

After finishing with her tits, I slid my mouth down 
between her legs. I started by placing some rough kisses 
on her inner thighs, between her pussy and the top of 
her thigh highs. Then I went up to her pussy. 

Her pussy lips were still distended and provided easy 
access for my mouth. Gripping one lip between my thumb 
and index finger, I stretched it even further as I 
sucked and licked from front to back. I then went on to 
the other.

When there was no flesh on her pussy lips untouched by 
my mouth, I noticed her clitoris was still swollen. This 
made an even more perfect target for me. I started by 
roughly licking the swollen clit but soon my lips sucked 
it half way down my throat as I abused it with my 
tongue.

Miss Witherspoon really started to squirm. The clit 
truly is the most sensitive part of a female. As I felt 
her start to orgasm, I stopped deciding to give her a 
taste of her own sadomasochistic medicine.

I grabbed two breast clamps and clipped them to her 
nipples making her eyes tear up. I took a bullet 
vibrator, turned it on, and duct taped it to her 
clitoris. I reached for the ten-inch hard-rubber anal 
dildo, lubed it up, and placed it under her butt on, but 
not in her asshole. 

Then I climbed between her legs and rammed my eight-inch 
cock brutally into her pussy hole. She wasn’t fully 
lubricated down there and the pain sent orgasmic waves 
throughout her body. 

I, however, was nowhere close to cumming. As her orgasm 
subsided I didn’t stop, I continued to plow into her 
cunt, but not in a loving way – hard and cruel, like a 
rape. Luckily for my comfort, she was becoming wetter 
down there.

The feeling of me relentlessly fucking her pussy, plus 
the arousal of the clitoral vibrator, had her cumming 
minutes later and when I still did not stop, her body 
exploded again, this time only moments after the last 
orgasm. 

I still wasn’t ready to give this bitch the satisfaction 
of my hot cum so I continued my hard fucking, even 
though there was no gap between her orgasms. Miss 
Witherspoon was screaming now and I could not tell if it 
was out of pleasure or pain so I decided to do one more 
thing.

As I was viciously fucking her pussy, and her body was 
shaking uncontrollably in a continuous orgasm, I reached 
down and plunged the ten-inch dildo into her ass hole.

That must have been the final straw because I heard her 
yelling, “Voltaire, Voltaire, Voltaire!” as her body 
exploded in one final orgasm. 

This triggered my ejaculation and after shooting three 
spurts inside of her pussy, I pulled out blasting the 
rest of my hot cum all over her tits and face.

She passed out and I took that time to unbind her, and 
remove the clamps, vibrator and dildo.

When she came to, she didn’t seem as angry as she did 
before she gave up. Miss Witherspoon led me into the 
shower so we could both clean up. The hot water seemed 
to have a healing effect on her messed up body.

As she enjoyed the hot, soothing spray she told me 
something.

“You know, as TA I’m in charge of grading all the 
undergraduate assignments. Instead of worrying about 
understanding Voltaire, let's just say you get an A for 
understanding my favorite French writer!” she said. 
“That is if you care to come back and explore things 
further.”

I jumped at the chance, knowing full well I would never 
be able to do any of these things with Nancy.

To be continued...

--------------------------------------------------------
This story was written as an adult fantasy. The author
does not condone the described behavior in real life in 
any way, shape or form. Anyone tempted to act out any of 
the scenarios in this story should seriously consider 
seeking professional help.
--------------------------------------------------------
Kristen's collection - Directory 82