I had known Jesse for many
months through mutual friends and always liked her, even though she was a bit
evasive when asked about dating. I knew she had an interest in S&M, but I
never suspected how extensive that interest was. I called her one evening to
tell her about a fetish special on cable and was very pleasantly surprised when
she invited me over to watch it with her. Even though I’ve never been involved
in any type of S&M activity, I’ve always been curious about it, although
ashamed to admit it as most men are. I have often gotten turned on watching a
straight movie with any type of bondage or showing a woman in control (I think
Catwoman or Mrs. Peel was every boy’s earliest fantasy), the biggest problem
was trying to hide the bulge in my pants if I was with company. Now I was
actually being given the opportunity to spend time with a woman who was
obviously very dominant and knowledgeable about things I was never able to
discuss with anyone. Knowing these things about her made me very surprised at
how nice a person she was, caring and funny, not the total bitch I always
suspected dominant women to be, so I was unafraid to be with her.
I arrived at her home in a secluded cul-de-sac, very
private and surrounded by trees. Jesse greeted me at the door wearing a black
shiny vinyl outfit that excited me just to look at it. She had it zipped up the
front just enough to give me a peek at her breasts without being able to really
see them. Her home was beautiful and her maid served wine and cheese before
being dismissed for the night. We had a friendly chat when the program started,
she enjoyed seeing other dominants’ equipment and unique styles and explained
a lot of the psychology to me. She often referred to these explanations as
teaching the “Dark Arts”, a term I learned to love. I was getting quite
aroused at her descriptions and found myself paying much more attention to her
than the program. She must have noticed rather quickly, as she invited me
upstairs to see her playrooms and toys.
I waltzed up the stairs behind her, conscious of
her short vinyl skirt and garters that gave a hint of what was underneath
without revealing too much. She had four different rooms set up for play, but
laughingly told me I could only have a tour if I removed all my clothes. I
laughed too, but could tell she was serious. This was quite a dilemma for me; to
be asked to get naked by a hot-looking woman was in itself embarrassing, but I
was dying to see the S&M toys and equipment first-hand. I kept grinning but
eventually said “What the hell” and headed for the closet. My natural
instinct was to close the door, but Jesse told me to leave it open so she could
watch the show. I was doubly embarrassed to look down and see a huge erection I
could no longer hide. This was a great source of amusement to her and she
grabbed me by the shaft and led me down the hall. The first thing I saw in a
very big room was a set of stocks with a high opening for head and hands and a
lower opening for cock and balls. I was amazed that people actually had this
stuff in their homes. She asked if I’d like to experience the helplessness of
light bondage and then perhaps the stocks and I nervously laughed and said
“Sure”.
“Are you in a relationship
at the moment?” When I replied “no”, she lead me to another room and said
“Great, lie down on the floor so I can do some prep work”. She put leather
wrist cuffs and a blindfold on me and clipped my hands to a hook on a bondage
horse. I could hear her leave the room and didn’t know it, but she returned
with a bowl of water and shaving cream. I could feel her
lather up my pubic area, explaining it would not only look nice but make
cock and ball bondage much easier. I was a little nervous but trusted her not to
hurt me. It felt very sensuous when she shaved me very gently with the razor,
especially not being able to see, and I was almost sorry when she was done. The
blindfold was removed and I was asked to please clean everything up and return
to her.
I did so as quickly as possible, again impressed that
she made a request instead of a harsh demand. I was told to stand up straight in
front of her and she put the blindfold back on and clipped my hands to a hook
hanging from the ceiling. My cock was still hard enough to cut diamonds all this
time and I could now feel her rubbing her breasts up against my back.
She also started gently
kissing the back of my neck until she moved around to the front. When she did,
she poured baby oil on the shaft of my cock and started rubbing it with her
hands. I thought I would lose it for sure, but every time I came close she
stopped and just laughed at me. This went on for at least 15 minutes, which
seemed like 15 hours to me and I could tell she was enjoying every minute of my
torment. I never thought I could stay that hard without cumming for so long, but
she gave me no choice. Just as I felt I was going to die from all this pleasure,
Jesse untied my hands and removed the wrist cuffs. The blindfold was left in
place and she lead me by my cock back to the bigger room. I was positioned
behind the stocks while she
adjusted the height of both openings to accomodate me. Once positioned inside,
she locked both pieces very quickly and I truly could not move anything. I
realized she could now do anything she wanted
and there was nothing I could do about it, I was truly at her mercy. I
was glad I trusted her and knew we were just playing around, so my erection kept
growing harder and harder until it was dark purple and throbbing. I could feel
all the veins sticking out and still she kept playing with the baby oil,
stroking my balls with her nails. I finally laughed a bit and told her I
honestly didn’t think I could hold it any longer. She had reached that fine
line where you need to orgasm so bad but don’t want things to end.
Finally she asked if I was ready to explore new areas and experience
different feelings. I think I would have done anything she asked. I heard her
take something off a shelf and before I knew it she was attaching clothes pins
all over my balls. They really pinched but she kept stroking my cock with the
oil, and the combined effect of intense pain and pleasure together was amazing.
If anyone had ever suggested I would be in bondage with clothespins on my balls
I would have told them they were crazy, but it was happening and I was loving
it....
She slowly started removing the pins one at a
time and moved two of them up to my nipples. Again it was a pinching sensation
but also stimulating in a very erotic way. While the clothespins were still on
my nipples, she walked around behind me and started lightly slapping my ass. I
started to laugh at first, mostly because I was embarrassed at how good it felt.
It didn’t hurt and I had never experienced so many different feelings at once
before. I heard her walk back to the shelf and when she returned behind me her
finger was lubricated with something she rubbed up and down the crack of my ass.
She gently found the opening and started to lightly probe it with her finger. I
was the usual scared male, thinking anything inserted there would be nothing but
painful, but she eased it inside so slowly it felt great.
She reached around and kept stroking my cock while she penetrated me with
her finger, and once again I thought I’d go crazy. Much to my disappointment,
she only did this a few minutes and then removed me from the stocks. I wanted
those feelings to go on forever and
was terrified she was bored and about to throw me out. Just then, she leaned
close to my ear and whispered, “Did you love it?”
“I’m kind of embarrassed
to admit it, but yes, I loved it”.
“Would you like to
experiment some more?” I could
feel her breath in my ear.
“Oh yes, please, anything.
You certainly know just what to do to me”.
Jesse laughed again and led
me still blindfolded up 3 steps and had me sit on the edge of a very large bed.
I felt her attaching leather ankle and wrist cuffs, and soon enough my legs were
hoisted up by pulleys in the ceiling. This put my legs in a V-shape which left
me wide open and vulnerable. My hands were then stretched out to the sides and
attached to chains hooked to the floor. She left me that way for a few minutes,
but when she returned my cock was again oiled and teased with one hand while she
inserted something long and skinny up my asshole. Whatever it was started to
vibrate and I thought, “This is it, there’s no way I’ll be able to hold it
now”. All of a sudden everything
stopped, which was hugely frustrating but also a big relief. She dried her hands
and climbed up on the bed very close to my face. “I’ll bet you’ve been
dying to peek up my skirt all evening, haven’t you?”
“Yes ma’am, I have to
admit it”. I could feel my face getting beet red.
“Well since you’ve been
so good about everything, I have a present for you”.
I could hear the rustle of
the vinyl as she hiked it up over her thighs and fully expected her to remove
the blindfold and sit on my face. Much to my surprise, she did neither. I felt
her back up a bit, and when she squatted over my right hand, I felt her slip
something long & rubbery into it.
I reached around as much as the chains would permit, and
realized Jesse was wearing a strap-on harness with a very big dildo in it. I
could also feel a condom covering it and was afraid to think what that might
mean.
“Not exactly what you were
expecting to find under my skirt, is it?”
“Uhh, no, not exactly”
This
felt very strange and awkward to me, holding a big dick in my hand. I
related it to touching another man which I never had a desire to do, but she
pulled down the zipper on the top of her outfit and put her left breast in my
mouth. This simple act eradicated all thoughts of other men, this was definitely
a very femine woman with a fake cock attached to her. She took her breast away
and I started stroking the dildo as if it were real and she started thrusting
back and forth. I could hear her moaning softly and she could tell how much it
was driving me crazy. I wanted this woman so bad and there was nothing I could
do. She laughed a bit and gently nudged the cock closer to my mouth. I laughed a
little too, and before I knew it I could feel the tip of the cock rubbing
against my lips. I stuck my tongue out and lightly licked at the dildo, feeling
it starting to get pretty wet. Jesse pressed her cock toward me harder and I
felt it going in a bit further with each thrust of her hips. Before long it was
moving quite deeply into my mouth and I was sucking on it as hard as I could.
She looked down at my raging hard-on and started stroking it again, taunting and
teasing while she pumped the dildo into my stretched mouth.
I still couldn’t believe all this was happening to me,
especially on a night I was only expecting to watch television. It actually was
much better that way, as she well knew, as I’m sure I would never have shown
up if I knew ahead of time what was going to happen. That would have been very
sad, as I would have missed out on one of the hottest experiences of my life.
As I kept sucking Jesse’s strap-on I could feel her
grinding above me and hear her moaning with pleasure. The base of the cock was
positioned over her pubic area, and the harder I sucked the more she came. I had
my hand on the shaft of the dildo and could feel her cum dripping down her legs
and onto my fingers. Nothing could make me happier than to be able to please
this erotic woman in some way, as she had already given me so much pleasure.
Eventually she let my hand free and stopped pumping my mouth. I reached up to
touch her breasts and then moved down so she could sit on my hand. I put my
fingers way up inside her, not believing how wet she was and how much she was
flooding down my arm and onto the bed. She reached over me and released my other
hand and then removed the blindfold. I was so caught up in the passion I hardly
knew where I was anymore. I sat up and put my mouth on her breast while she
reached down and started stroking me again, much harder this time. In no time at
all, I shot a load that covered my chest and reached parts of my face. It felt
like it lasted for minutes and the feeling was incredible. It was the most
intense release I’d ever had. The room reeked of sex and yet we’d never
gotten close to intercourse. I was completely spellbound and so weak I
couldn’t have stood up if the house was on fire. We sat on the bed and drank
wine and chatted to unwind, and it was a good half hour before I was capable of
taking a shower.
If anyone would have ever told me I could have a better climax by not actually having sex, I never would have believed. But there I was, living proof, on the best night of my life. So if Jesse ever invites you over to watch TV, drop everything and get over there.....