Guided Masturbation Stories


In the PeterFiles, masturbators are often justly condemned to cold, 
cruel, institutional situations. But sometimes female guidance is 
provided in a gentle, loving relationship. The PeterFile theme requires 
only that the female be unequivocally in control of the male's non-
coital consummation. 

Here is a pleasant story by a correspondent known to me as "Richard" 
(not me). The man is shy and uncertain; the woman is confident of her 
womanly power over him and controls the pace of the relationship. I 
especially enjoy the element of almost ritualistic breast worship. 
-- R.L.

 

Rachel

by Richard 

from the net, circa 1998

Though it happened eight years ago, it hangs in my mind as if it took 
place yesterday. I have tried to reconstruct a little dialogue at a few 
crucial moments though I'm sure the exact words were different. It was 
my first year in Southeast Connecticut where I had recently arrived in 
January as a young professor in the humanities. Having recently 
purchased a CD player without realizing the major expense would be 
compact discs, I was glad to find an extensive collection of classical 
CDs at the local library. These could be checked out for two weeks 
intervals just like books. I was even more happy to meet the librarian 
who handled the music section. 

Let's call her Rachel to protect the innocent (or, on this case, 
not so innocent!). Rachel was one of those women who naturally exuded 
the radiant warmth of an earth mother (despite her young age of 25) 
while at the same time being unbelievably sexy and feminine (at least in 
my eyes). I was immediately drawn to her infectious laugh, sparkling 
personality, and somewhat flirtatious manner. I would be lying if I 
didn't admit I was also taken with her luscious breasts which she seemed 
to emphasize by wearing clingy tops. Rachel had lustrous black hair 
which cascaded thickly around her face and over her shoulders and set 
off her smooth, pearly white skin. Her eyes matched her hair and flashed 
like dark jewels. Most of my attention, however, was usually riveted on 
her heart-stopping hourglass figure. Her hips swept out from her waist 
with large, full curves which rolled sensuously back and forth with 
every step. As if in musical counterpoint, her lush, Junoesque breasts 
accented these larger movements, swaying heavily beneath her knits, 
sweaters, and silk blouses. While I have always been a sucker for full 
women, I was mesmerized by Rachel's ripe femininity. Needless to say, it 
wasn't long before I began visiting the library more often to try more 
classical CDs and get Rachel's advice on all things musical. 

Since I have never been good at hiding my feelings, it wasn't long 
before Rachel realized I was a not so secret admirer with more than 
classical music on my mind. Within a few weeks of meeting, I was 
stopping by twice a week and sometimes more often if I was "in the 
area". After a month, I even got up the nerve to flirt indirectly with 
her by commenting on the beautifully plump female nudes painted by the 
Old Masters which decorated the jewel boxes of so many of the library's 
classical CDs. She also caught me staring at her a few times. 
Fortunately, she always seemed to appreciate my attention. At times, she 
even responded with flirtatious remarks herself. For example, when I 
commented that the Old Masters really knew what beautiful women looked 
like, she said it was too bad more men didn't feel that way. By early 
April, we were on quite friendly terms. 

Sometime in late May, Rachel inherited some lithographs from an 
uncle who had recently died. Since she knew I had a good amateur's 
knowledge of art coming in part from my family background - my parents 
stilled owned a small print gallery - she asked me if I would be willing 
to look her at her lithographs to see if they were valuable. Of course, 
I agreed, excited at the chance to socialize with her outside the 
library. The following evening, I arrived at her apartment around 6:00. 
When she opened the door, I noticed immediately that she had changed 
into much sexier clothes than the ones usually worn at work. She had on 
a gauzy white linen summer skirt which made her hips look softer, 
fuller, and more pliant than ever. As pretty as that looked, my 
attention was primarily drawn to her thin pink sweater-jersey which 
buttoned down the front. I should say "unbuttoned" because the upper 
three or four buttons were undone allowing a generous view of her heart-
stopping cleavage. Even fully buttoned up, that sweater would have 
caught my eye the way it clung like a second skin. One could see the 
distinct outline of a low cut, tight brassiere which bit slightly into 
her breasts so that the top half bulged over and jiggled freely where 
the sweater was unbuttoned. Equally distracting was the wide spacing of 
the sweater buttons which created numerous little gaps down the front 
and gave me repeated, fragmentary glimpses of the lacey pink cups of her 
bra. Later, Rachel admitted she carefully choose her outfit that night 
to try to seduce me.

After chatting in the living room over a glass of wine, Rachel 
brought out her lithographs. Fortunately for me, I was able to identify 
them as unsigned originals of the late nineteenth-century French artist, 
Daumier. Since these works were produced in large numbers and are still 
quite common in print galleries, they would have been familiar to anyone 
with a basic background in art. I was even able to suggest rough 
estimate of their value - approximately 300-400.00 each. 

With business taken care of, Rachel gave me a tour of the other art 
works in the house, notably some interesting coastal watercolors and two 
still-lifes. Also framed was a Renoir exhibition poster featuring one of 
his plump female nudes. After we were all finished, she asked, "Which 
one do you think is the most beautiful, Richard?" I nodded to one of her 
coastal scenes as far as her original art went but added I thought the 
Renoir even more beautiful. I even managed to say that looking directly 
at her face though not without feeling my heart beat faster. Rachel told 
me she wasn't surprised and again lamented that more men didn't share my 
views on beauty. 

With little remarks like that combined with the luscious spectacle 
of her half- unbuttoned sweater, I felt my face grow increasingly 
flushed as the room took on an increasingly charged atmosphere. Indeed, 
I breathed a little inward sigh of relief when Rachel announced she was 
off to the kitchen to fetch more wine. I tried to relax by sitting down 
on the sofa and taking a few deep breaths. Of course, it didn't work. 
After about two minutes, she finally emerged with the wine bottle. As 
soon as she appeared in the kitchen door, an electric jolt hit me and my 
heart began pounding. For it was obvious Rachel had removed her 
brassiere in the kitchen while undoing another button for good measure. 

Since the CD had just ended, she crossed over to the stereo, set the 
wine bottle down, and began shuffling through a large pile of CDs. It 
took her almost two full minutes to select "just the right music". By 
then, it dawned on me that she was playing a little game and that I was 
free to play along as long as neither of us openly acknowledged it. For 
the whole point of her lengthy CD search was to allow me to stare 
without being caught. And stare I did at the pretty rolling of her 
unconfined breasts beneath the thin sweater. Every movement she made 
with her body was picked up transmitted outward into her breasts in a 
series of smaller dancing movements. And to top it off, Rachel managed 
to chat on amiably and innocently about music selections the whole time 
as if nothing was amiss. Finally, she found the CD and got it playing. 
With that done, she retrieved the wine bottle, crossed over to the 
rather low coffee table and leaned forward towards me to fill our 
glasses. And when she did, the upper half of her unbuttoned sweater 
simply fell away revealing two pillowy white, jostling breasts held 
loosely in place from below. Even if she hadn't been preoccupied in 
pouring wine, it would have been impossible not to stare. Held together 
by the tight sweater, her globes wobbled gently like Jell-O patties with 
every slight shift in her position. 

With my heart pounding and my senses dazed, I forgot about all else 
and stared shamelessly even though she was a few feet away at best. 
Fortunately, Rachel was busy carefully pouring the wine. Though a little 
voice inside told me to stop gawking before she saw me, I ignored it, 
glued to the sight of so much femininity. Eventually, of course, it was 
too late. I looked up to see her dark eyes looking directly into mine. 
But instead of standing up abruptly in embarrassment, Rachel continued 
to hold her position - the second glass was not quite full - as if to 
use her knowingly-exposed breasts and my rapt attention to test me 
further. She then asked in a noticeably husky voice, 

"Do you see anything else around here that's beautiful, Richard?" 

Throwing all caution to the wind and lowering my gaze very 
deliberately to feast even more openly on her breasts, I answered, 

"Ooh God Rachel ... I sure do". 

"Then stay there. I think I know exactly what you need." 

With that, she put down the wine bottle, came around the coffee 
table and sat beside me on the sofa. And without saying a word, she 
gently pulled my torso into her lap so that my head was cradled in her 
arms. Even before she finished adjusting me, my open mouth instinctively 
sought out and found a nipple through the thin sweater and begun 
suckling hungrily. After a few moments, she gently pushed my face away 
and pulled at the sweater, popping the remaining buttons in a rush. 
Instantly my face was buried in warm breast flesh. Completely overcome, 
I again fastened my mouth around the nearest nipple with a moan and 
began sucking for dear life. In return, Rachel began softly moaning 
herself and lowered her breasts further so they completely enfolded my 
face. As I licked and sucked, my hands came into play as well, cupping 
and squeezing the warm bosom I was suckling and periodically giving her 
other waiting breast some attention too. As I suckled and fondled her, 
she stroked my face and head repeatedly and murmured, 

"Oh you sweet thing... you dear, sweet thing. You've had your eyes 
on me for months now, haven't you? I thought you might need something 
like this from Rachel. I'll tell you a secret, Richard. Some women need 
this just as much. Oooohh yes, that's it ... keep sucking my nipples. 
I've been thinking about this for longer than you might think. My, my 
... you certainly do a thorough job, don't you. I think we're going to 
have to get you to come by here more often, what do you think?" 

By then, all I could do was nod from the trance-like reverie of my 
oral pleasure. For at least the next hour, the only sounds I made were 
the licking, kissing, and sucking noises of my busy mouth, my breathing 
through my nose and a series of little moans. After ten minutes, I 
shifted to bury my face in her other warm breast only to dart back again 
to the other as if determined to satisfy both of them together. All the 
while, she encouraged me with a steady stream of soft words, moans, and 
head caresses. When I opened my eyes a few times to see what she was 
doing, she too seemed to have slipped off into a pleasure trance. Her 
eyes were closed and her breathing irregular and heavy. 

I don't know how long I stayed there as I lost all track of time. 
At some point, I noticed it had gotten quite dark outside. My guess is 
that I suckled Rachel for more an thirty minutes that first time. And 
thus began a weekly routine of long sessions that lasted sixteen months 
years before Rachel moved to a better job in Atlanta. We were a perfect 
match. For me, breast suckling and squeezing was the most sensual thing 
I knew. I even came a few times with all of my clothes on just from 
being so turned on. (I was always hard as a rock when my head was in her 
lap. And she would often bring me off with her hand.) Rachel, in turn, 
looked forward to our sessions just as much. During the first episode, 
she confided that her breasts and nipples were so sensitive she 
frequently had orgasms just from having them sucked. Needless to say, I 
made sure she had plenty of breast-induced orgasms over the next year 
and a half. 

At times, we would vary our routine. Sometimes, she would drive 
around at dusk or at night (or even on quiet roads in the day) with me 
lying on my back across from the passenger seat with my head in her lap 
and my face buried in her breasts. Sometimes she simply tucked my head 
under a loose sweater worn without blouse or bra so that my head was 
invisible. At other times, she wore a silk blouse completely unbuttoned 
so that her breasts swayed down openly slapping my face like ripe, 
teasing fruits with every motion of the car. She also liked being finger 
fucked while she drove. When summer came, we went to summer movie 
matinees on weekdays and sat in the back. Since the theaters were 
invariably deserted at that hour, we had hours of uninterrupted breast 
fondling while her hand quietly caressed me through my pants. Until we 
reached our seat, we looked like any respectable couple. She wore a 
light summer jacket which was buttoned shut decorously in front. Once 
the theatre lights went down, I would unbutton her jacket and open it 
slightly to reveal her unconfined breasts outlined in a stretchy knit 
blouse. With Rachel in a dark blouse under a jacket, we found I could 
fondle her breasts as much as I wanted during the movie. For anyone 
passing by, nothing was visible, not even the movements of my hand. 
Since she also loved being fingered, she always wore full skirts and no 
panties. I would switch off three or four times an hour between 
squeezing her breasts and finger fucking. Concealed by her full skirt, 
my hand could easily creep over her nearby thigh and slowly, ever so 
slowly slide deep into the warm, feminine prison of her two wonderfully 
soft, fat thighs. To heighten this for both of us, I always took two or 
three minutes to reach my goal. In turn, she teased me by repeatedly 
squeezing my hand between her thighs, thereby simultaneously halting me 
and encouraging me with these intimate love squeezes. After a moment, 
she would loosen her thighs just enough for my fingers to move further 
in their journey. Not surprisingly, she was usually sopping wet by the 
time I finally reached her womanhood (especially since she was already 
fingered on the drive over). At that point, she opened her thighs to 
give me sufficient room without freeing me from the enveloping feminine 
plumpness of her thigh flesh. It wasn't long before such slow finger 
fucking turned me on enough to bring on a climax assisted by her quietly 
squeezing hand. 

I know how much she liked being fingered not just because she told 
me but because she stiffened periodically and locked my hand in a deep 
thigh squeeze while sighing quietly under her breath for a half minute 
or so. She also conveyed her pleasure in her considerable lubrication. 
Though we never saw much of the movies, we nonetheless enjoyed the show 
thoroughly. 

Finally, there were times when she would call me to say she needed 
a shampoo. When I arrived, I usually found her sitting on a kitchen 
chair in the bathroom and wearing a thin Italian tee-shirt and a tennis 
skirt. I would lather her head up with lots of extra shampoo and 
eventually let my soap-filled hands descend slowly along her ears and 
neck to the outside of her tee shirt for an extended soapy breast 
massage. Eventually, my hands would find themselves under her little tee 
shirt and complete the job paying particular attention to her sensitive 
nipples. Sometimes I would descend even further and soap her thoroughly 
between her thighs right through her panties (if she was wearing any). 
Most of the time, after she had come once or twice, she would guide me 
around in front of her, lower my pants, and ask me to make love to her 
soapy breasts. Or we would move into the shower, sometimes still 
dressed, for more soapy, watery games. On still other occasions, we 
would give each other sponge baths one after another. 

We also loved going for afternoon weekday swims in the summer in warm 
deserted CT lakes. Even if there were a few fishermen in aluminum boats 
in the distance, we were invisible once we waded out into neck deep 
water. Our suits always came off rather quickly at that point and the 
rest of our time was spent squeezing and cupping and stroking 
underwater, safe from view. 

- end -