First major post-divorce relationship, with side benefits
It Started At The Pool
Since my divorce (7 years ago) I've been dating, but have managed to not find anyone
that I've been interested in sufficiently to marry or have a permanent commitment with.
Within the past year, that had changed as the relationship I'm in with a wonderful woman
I met at the YMCA matured, but didn't meet Cindy directly at the pool. Rather, thats where I
met her daughter (Jen), and she's the that got us together.
I visit the local YMCA to stay in shape, and my preferred exercise is swimming laps. I've
been doing this for years on and off, but now I've been doing so steadily for quite a while
and its become a habit. The times I visit the Y have varied depending on how busy I was
at work, or if I happened to be in between projects I could go during the daytime when there
was a lot more room (if you go during the busy times, you have to minimally share a lane,
do circles with 3 people, or otherwise have to wait).
After you've been hanging around any gym or pool for a while, you start to recognize
people and get to know them (i.e. "the regulars"). One of the things that I happen to like
about swimming is because I appreciate women who take the time to stay in shape, and
women who swim tend to have nicely toned figures. As an added bonus, they generally
have to wear swimsuits which reveal exactly how in shape they really are - even when
wearing the standard Speedo. Its typical to wear goggles when swimming so you can
see where you're going, and one of the benefits is that you also get to see the women
swimming which to me is an added bonus.
While I'd been going I had noticed a young woman who swam at the same time I did and
was a regular. She was maybe 5'2" and had a slim, tight, a fairly shapely figure, and very
blue eyes. I had just completed swimming a mile was taking the time to cool down before
getting out. She had also apparently just finished her workout and was hanging out in
the lane next to mine. We started to chat, and had a few laughs when I announced that
I was getting out to move over to the hydro-spa for a while before heading out. So I swam
over to the ladder and climbed out, picked up my towel and walked over to the spa and
settled in. I really enjoy the spa because you really got to decompress as all the air bubbles
massaged your body deeply in the hot water, and worked out any aches or pains.
This same woman came wandering over and also got into the spa, smiled at me, said "hello
again". So we started chatting again, and I learned her name was Jen, and I told her mine
was Greg. After chatting for a while I realized she was too young for me (she was in her early
20's, and I was in my later 40's) I came to the conclusion there was no reason to build any
interest in her (for other than sporting purposes!). Anyway, I had an appointment to go to
that afternoon so I excused myself and headed off to the locker room.
I started running into Jen fairly often, and saw her several times a week. And as usual we'd
often end up in the spa after our workouts and just chat. But one day, she started asking
some really personal questions ("do you have a girlfriend?", "what do you like to do for
fun?", "where do you live?", "how old are you?", etc.). Now I'm still in pretty good shape
due to my keeping up with my exercise, and when I swim (as is common) I wear a swim cap.
Jen mentioned to me that she was surprised at how old I was (I've managed to retain a
fairly youthful appearance) after I removed my swim cap, which revealed my grayed temples
and brown hair.
I'd started asking her what she did for fun, where do you live, etc., to see where the
conversation was going, and then she told me she'd wondered if I would be interested in
meeting her mom (a-ha!). So I asked her what her mom looks like, and she said "she looks
just like me, only 22 years older…". Jen started telling me her mom was divorced, and her
father lived on the other side of the country. Apparently, they just didn't get along and so
they decided to separate when her father was offered a position in Los Angeles. He left her
with the house and Jen had been given the option of living with either parent. She opted
for her mother because she grew up here, all her friends were here, was in school, etc.
Her mom worked in sales in a local pharmaceutical company, and while a lot of her clients
were local, she did have to travel from time to time. We had discussed (while hanging
around in the hydro-spa) a number of things I liked to do (travel, hiking, camping, etc.)
and she thought we'd hit it off great because thats what her mom enjoyed as well, and her
mom also liked to swim.
Jen suggested we meet at the pool over the weekend and she'd bring her mother along. So
I figured what the heck - if her mom looked like she did that could very well prove interesting.
We arranged a time, and I went to the pool the following Sunday afternoon and jumped in
to do my usual routine. Before long I saw two women in the lane next to mine, and the shape
looked just like Jens. So I stood up at the wall at the end of the pool and said "hi Jen…" and
the woman answered back "I'm not Jen, I'm Cindy… Are you Greg?" to which I answered in
the affirmative (Jen wasn't kidding - they almost looked like sisters!). Jen finished a lap at
that same end of the pool and stood up, noted that we'd already met, and joined in on the
conversation. So we determined we'd finish our laps and meet in the hydro-spa.
I cranked through the rest of my workout, rested for a few moments, and headed for the spa.
I'd just about settled in when I saw Jen and Cindy get out of the pool (Cindy was maybe an
inch taller than Jen, with a virtually identical figure, and slightly larger breasts). They were
both smiling as they walked over to the spa, dropped their towels, and got into the spa over
by where I was sitting (the spa could fit ten people comfortably). We all got along great, and
had a lot of laughs. Cindy was really nice, very articulate, easy to talk to, and seemed really
down to earth. Jen got up to go and meet someone she knew who came into the pool area
just as a few other people joined us in the spa, and Cindy moved even closer to me (now
we were almost touching) and I noted her nipples sticking out through her bathing suit.
She then told me that Jen had told her about me, and said that she always seemed to have
a good sense of judgement, which was why she came to the pool that day. I told her I hoped
I lived up to whatever Jen had told her about me, and she grinned. So I suggested we get
out of the spa (it had been a while) and lets meet out in the lobby and take it from there. She
said that sounded like a plan and so off the to showers we went. 20 minutes later I walked
into the lobby to find Jen and Cindy waiting for me, and Jen suggested we go to the local
tavern for a late lunch. That was fine with me, and 10 minutes later we were sitting at a table,
me across from two nearly identical women (the family resemblance was astonishing) with
my mind churning over how pretty the two of them were. When they got up to head for the
ladies room I watched two beautiful bodies walk away from me, asses swaying in near
perfect, and very sexy unison (I was under the distinct impression that Jen was exaggerating
her walk a little - her walk was very sensuous).
When they came back a few minutes later I was pretending to read the menu, but was
stealing looks at both of them as they walked to our booth and squeezed into the other
side. So we started off with a few drinks, ordered lunch and chatted when Jen's phone
beeped, and she pulled it out and started to frantically compose a text. So Cindy and I
continued talking (where had she been hiking, traveling to, etc.) and traded some stories
while waiting for our lunches to arrive. Jen rejoined the conversation and shortly
thereafter a very pretty young lady showed up and came over to our table. Jen jumped
up and gave her a big hug, introduced her as Diane, a friend of hers from college (Jen
went to a local school, but stayed in a dorm during the week, and came to her mothers
house over the weekends). She asked if we minded if she and Diane got another table,
and that didn't bother either of us, so they chose a table on the other side of the dining area.
Cindy and I had a great conversation, a nice lunch, traded cell numbers, and jointly
determined it would be fun to do something together. We all finished up at about the same
time, so I bid them all good by, hugs all around, and headed home.
When I saw Jen at the pool the following Tuesday she told me her mom really liked me
and would really like to see me again. We chatted as usual and completed our laps
in the pool while I really enjoyed watching Jen's lovely body move through the water (I
did lose count a number of times!).
The next day I called Cindy to see if she might be interested in going out for dinner and
the theater on Sunday (the following Monday was a holiday), and she immediately
accepted. So on Sunday I dressed for an evening at the theater and went to pick up
her up. She lived in a nice part of town and had a large, expanded ranch house that
was nicely landscaped. I went up to the door which opened before I rang the bell to
be greeted with a hug by Cindy who was wearing very flattering little black dress. She
invited me in for a cocktail before dinner and I happily accepted, and followed her into
The dress she wore showed her tight figure to advantage, and I marveled at the sway
of her ass as she led me into the kitchen. She motioned for me to sit at the bar in the kitchen
while she poured us each a glass of bourbon (she likes bourbon!), pulled up another
stool and sat close as we talked about places we wanted to travel to. But time began
to run short as I'd made a dinner reservation, so we downed our drinks and got up to
go. She went over to the closet on the way out, pulled out a lovely cloak which I put over
her shoulders and after locking the door on the way out she took my arm and we strolled
to the car.
Dinner was excellent, and we had just enough time to make it to the theater and get settled
in when the show started. There were a few suspenseful moments during the show where
Cindy grasped my arm or hand, and whenever I looked at her she gave me a big smile.
The show ended so we headed back to the car arm in arm, laughing all the way. The
ride to her house seemed really short, but she invited me in for a nightcap which I accepted.
We got in, and she kicked off her shoes, hung up her cloak and told me to sit on the sofa
while she went to the kitchen to get us our drinks. When she came back, she had almost
filled these two rock glasses with bourbon and when she noted my surprise, said "well, I
don't have to work tomorrow, do you?". I answered "no", so that settled that. She went and
turned on some jazz at a low volume, and came and sat next to me on the sofa. We clinked
our glasses and started working on our bourbons. A number of sips and laughs later Cindy
was patting my leg and arm with her hands as she had turned towards me (I was trying to
avoid looking up her legs) with her eyes shining and a nice smile. When she leaned
towards me I leaned in, gave her a little kiss, and she kissed me back with her mouth just
slightly open, and let it linger.
She got up and took me by the hand and asked me if I wanted to see the yard, so I said
sure. She led me through the kitchen and out the back door, where she had a really nice
patio with lighting bright enough so you could clearly see your way around, but soft enough
so you could still see the stars. We continued chatting and sipping our bourbon (I was
starting to catch a buzz) when Cindy mentioned that it was kind of chilly, so I took off my
sport coat and wrapped it around her, when she turned and offered her face up to me so I bent
down to kiss her again. This time, her mouth opened, her arms wrapped around my neck,
and she pushed herself to me as my arms circled around her back and our lips and tongues
We kissed deeply for a few minutes, when she broke it off, and led me back into the house.
We went back to the living room, asked me to sit and said she'd be back in a minute.
When she returned a few minutes later, the lights dimmed further and as she walked around
the sofa to me my breathing almost stopped when I noticed Cindy was now wearing a black
and rather sheer robe. She turned around and sat on my lap and pulled my face to hers and
kissed me fiercely. As I put my arms around her and traced her body I could feel no bra, yet
she had retained a thong. The kissing got hotter as she started to unbutton my shirt, and
slipped her hands inside to feel my chest. I moved my hand up to cup her breast, which was
very warm, and I felt her nipple hard against the palm of my hand. My other hand traced her
legs as the bottom of her robe started falling open.
By now I was quite certain that Cindy could feel my cock poking her as she was sitting on my lap,
when she got up, took me by the hand, and led me down the hall to the master bedroom. The
lights were already dimmed, and I noticed her black dress draped over the chair at her dressing
table. She turned around just as we reached the bed, slowly opened her robe, and let it fall
off her shoulders but hanging on her arms. Her body was exquisite, her breasts firm, nipples
erect, stomach flat, and as the robe slipped off her arms it revealed a lovely little thong with nary
a hair in view. Cindy draped her robe over the chair next to the bed and started to help me
undress. She tugged at my belt and undid the clasp of my slacks while I finished pulling off my
shirt. When she pulled the zipper down my slacks fell to the floor and I stepped out of them.
Cindy cooed as she cupped my now stiff cock that was straining inside my boxers, and again
pushed herself into me as we ran our hands over each others bodies and kissed frantically. Just
as I reached between her legs to cup her pussy she pushed my boxers down, releasing my 7
inches and pulled me to the bed. She lay back on the bed and continued pulling me to her, when
I reached for her thong and tugged at the strings on each side while she lifted her ass to make it
easy to take off. Her pussy was bare, with blond pussy hair above her clit trimmed and shaved
into the shape of a slight triangle. When she opened her legs more after I had pulled her thong
off I noticed that the lips of her pussy were slightly opened, indicating she was already wet.
I lay down beside her and we both clamped onto each other, running our hands up and down
each others body, exploring, touching, squeezing, and caressing. My mind was racing as I
tried to calm myself to enjoy the feeling of Cindy's body, which rivaled that of many women
who were much younger. I ran my hands down her back as we lay on our sides as we kissed,
cupping her ass. Her muscles flexed as my hand squeezed her butt, and I let my fingers wander
down below to the space between her legs as she ground herself into me. My fingers came into
contact with the lips of her pussy, which were already saturated with her juices. As I probed her
pussy with my fingers she moaned and lifted her leg over mine and reached down to guide my
almost painfully hard cock between her legs.
As the head of my cock found the lips of her pussy, she moved her hips back and forth, soaking
the head and shaft of my cock. I readjusted myself a little and started to slip my cock into her
opening, and felt it make room for the head of my cock. Cindy and I both moved at the same
time so that I would end up on top of her as I raised myself up with the head of my cock still
lodged in her opening, and then slid into her. She raised and opened her legs as she pulled
me down and my shaft into her. Her pussy, while hot and wet, had a tightness that resisted my
cock initially as I worked into her. When our pelvic bones met and my balls were resting
against her pussy, I lowered myself down to suck her nipples, and moved up her neck,
eventually kissing her deeply.
Our bodies started moving together, and when they were moving too much to kiss we
escalated to pure unadulterated screwing. Her pussy clenched at my shaft as I drove into her
and our bodies slammed together. The smell of sex permeated the room and I saw the light
reflecting off the shaft of my wet cock as it moved in and out of her pussy. Cindy was moaning
passionately as she thrust her body up to meet mine, and I felt the slickness and heat of her
pussy as it sucked me in. She suddenly shuddered and cried out as her pussy gripped me
so hard I almost slipped out of her - but I drove it back in and fucked her like a piston as her cum
flowed out of her pussy, soaking my balls, and leaked onto the sheets.
As she calmed down, she held my body close until her sensitivity subsided, and I started moving
in and out of her again. I ran my hands all over her as we fucked, kissed deeply, and fucked
some more. Finally I felt the need to seed building, and she sensed it was coming because
she wrapped her legs around my ass and pounded back up at me and clenched the shaft of
my dick as I pulled out of her. I couldn't hold out any longer and sent a number of jets of hot
sperm into her womb - Cindy cried out as she came again. We lay there together, and
eventually my dick slipped out of her as I moved over to lay on my side.
Cindy had a nice, rather glazed look on her face, which was almost glowing. She started
running her hands up and down my body and started to kiss me all over, working her way
down to my cock which she sucked into her mouth. She pushed me onto my back and
took me entirely into her mouth as she ran her tongue all around my shaft and head, sucking
it gently, but with purpose. I pulled her body over to me and ran my tongue around her
clitoris, which caused her to moan as she spread her legs and pushed her pussy to my face,
working us into a sixty-nine.
We were hotly locked together, practically in competition to see who could suck each other
into submission faster. When I took her clit between my lips and sucked it into my mouth
she gasped saying "oh my God…" and started panting and rubbing her pussy over my
mouth. He hips gyrated and her pussy ground against my lips as I sucked her, when she
shrieked and rewarded me with another flood of pussy juice that I happily lapped up. Cindy
lifted herself up, and straddled my now hard cock with her pussy lips, slowly moving her
hips back and forth. She leaned forward and kissed me deeply as she slowly took my cock
inside once again. I reached up and rubbed her nipples, and move my hands down her
body as she gyrated over me. I eventually moved one of my hands to her pussy and used
my thumb to massage her clit as she fucked me. That had the desired effect as her gyrations
rapidly increased and she bounced up and down on my cock, as her pussy nipped and
grasped my cock as she moved.
This time, watching this lovely woman impaling herself on my cock with such lust really turned
me on even more, and I thrust up into her as I emptied my balls into her womb once again. She
rolled off of me, looking satisfied with herself, onto her side. We held each other, kissing, and
then gradually fell asleep.
We woke up the next morning, with the bedroom door still ajar, hearing noises in the kitchen.
Cindy looked rather alarmed at first, put on her robe and went out into the hall. She soon
came back, and said that Jen was making coffee and breakfast. She'd forgotten that Jen
had come home and stayed Sunday night (it was a long weekend, and Jen would be leaving
for school late Monday afternoon). Cindy mentioned that she hoped Jen hadn't heard us
last night, but the lights had been left on (albeit low), and the door to the master bedroom
had been left ajar (whoops!).
Before we went out to join Jen, she shut the door to the bedroom, and said she hoped that
I wouldn't think less of her for being so forward with me (!) on a first date. I told her not to
worry about it, that I had had a wonderful time, and pulled her to me for a smoldering kiss.
She returned the kiss as we ran our hands all over each other, got dressed, and went off
to the kitchen to have breakfast with Jen (who had greeted us both with a large smile).
Cindy and I had really hit it off, and she was wonderful in the sack and had a really sweet
disposition. Eventually we'd started to coordinate vacations and travel together. She was
great to travel with, and had a great sense of humor when visiting other countries and
things didn't work out exactly as planned. Eventually we went camping and hiking, and it
seemed no matter where we went she was dressed the right way and handled it like a pro.
She was a great cook; I also knew my way round the kitchen, and made different stuff
so we seemed to compliment each other really well. I found myself really becoming attached
to this woman. She later sat me down, said she loved me deeply, wanted to be with me,
and asked if I would move in with her. I told her I would consider it, and eventually decided
to do so. She certainly had plenty of room, and had several unused rooms in the finished
basement for my personal stuff, storage, and for me to have a large private office.
Everything with this relationship seemed breathtakingly normal and stress-free: our families
got on great, lots of wonderful and energetic sex, and we both had the space we needed with
and without each other. Eventually, Cindy was asked to take on more responsibility at work,
which meant she would have to travel for roughly a week out of a month (thats not a big deal),
and since it came with a considerable raise we discussed it and she decided to go with it.
After Moving In.
Everything proceeded as it had before and remained pretty normal except that Jen would
sometimes spend more time at home when her mother was away on business. Once in a
while, Jen's friend Diane would come with her and spend the night or a few days at the
house. It didn't hurt my feelings to have two great looking young women hanging around the
house. And as is typical, I would run into Jen at the pool where I really enjoyed watching her
As Jen and I became used to having each other around clearly our comfort levels increased
and we chatted about things of a more personal nature. I enjoyed her company and as time
passed we'd occasionally watch movies together. If I was hanging around the house and/or
working from home I would typically wear sweats, and she'd usually wear yoga pants or
the PJ's that have become so common amongst college kids. As the summer progressed she
would sometimes wear very little around the house, which didn't generally bother me. One
evening I was watching some movie when she came in to join me wearing a teddy and a pair
of panties and my jaw visibly dropped when she plopped down on the sofa.
She saw my reaction and said "what's the big deal? You've seen me wearing a lot less than
this at the pool, and this is comfortable". "Good point", I replied. I was thinking, however, that
panties have a lot more transparency in a sense, as they don't have additional reinforcement
and layers in the seat. Being a guy (and enjoying seeing scantily clad women) I wasn't going
to argue with her. Jen would soon be wearing only panties (or short-shorts) and a t-shirt around
the house or when she was in her mothers office when studying. And since Cindy didn't say
anything about her clothing choices when she was home, I assumed it wasn't unusual.
One of my clients then asked me to take a trip out to Seattle at the same time Cindy was, so we
told Jen we'd both be out of town. She said that was fine, but she'd probably be at school and I
didn't think anything about it. Eventually I left for my trip with Cindy (we shared a car to the
airport as we were leaving within a half-hour of each other) and we were both going to be away
for the week.
My meetings were incredibly productive, and since my clients had had some other events get
cancelled, we made far more progress than expected and finished early. I called the travel
desk at my clients and they arranged for me to get a flight home on Thursday instead of Friday.
I took a taxi home from the airport and was surprised to see Jen's car in the driveway. I let myself
in through the door next to the garage, because I could drop my lap-top and business stuff in my
office on the way upstairs. The house was pretty dark despite it being only around 10 PM, and I'd
noted that Jen's room light was the only one on when the cab pulled up to the house. So I climbed
the stairs and walked with my bag to our bedroom, when I noticed that Jen's door was ajar, and I was
going to say hello when I heard a loud moan come out of her room. I took a look into her room
though the crack in the door and saw Jen and Diane naked on her bed, in a sixty-nine. My heart
practically stopped and my cock instantly stiffened as I watched these two petite young women
with their faces buried in each others pussy as they writhed in pleasure, moaning and clamped
I just stood there watching the two of them as I slowly set my bag down and pulled out my rock-hard
cock and started stroking it. The scene was so erotic - I had of course watched lesbian porn and
had studied it carefully to get pointers in how best to eat pussy, and hopefully make any woman I was
in bed with delirious. But seeing it live in the flesh with such beautiful young women was entirely
different, and they had apparently been at it for a while because the odors of sex were apparent, and
Jen's bed was fairly close to the door so they were maybe 6 feet away from where I was standing.
Fortunately, I hadn't bothered turning on the hallway light so they couldn't see me watching them
through the crack in the door. Jen's and Diane's pussies were completely shaved, and both women
were digging into each other, alternating between tongue-fucking, and licking and sucking each
I continued stroking my cock as they licked themselves into a frenzy, moaning louder as the minutes
passed. They came within a few seconds of each other, and as they lifted their faces away from each
others pussy the wetness was obvious. They both got up onto their knees and kissed deeply, mashing
their breasts together nipple-to-nipple, fingering each other as they rubbed their sweaty bodies together.
Then they both sat down on the bed facing each other, intertwined their legs and pushed themselves
together and started scissoring their crotches, rubbing their obviously soaked pussies and clits as the
sound of wetness and smell of pussy permeated the air. I watched for several minutes, as the grinding
of these young bodies, their breasts heaving, reducing these two into pure animalistic, lusty sex fiends
as they both moaned and cried out when they came.
That was it for me, I gave it one more stroke, and came so hard that I squirt semen all over her door, the
wall, and through the crack of the door onto the carpet in her room (not much, but visible nonetheless).
I pulled my shirt off, and cleaned up as much as I could and tiptoed off to the bedroom, my heart pounding
like a drum.
I quietly closed the door and deliberately kept the light on really low as I didn't really want to reveal my
presence, got undressed and considered what I had just witnessed. My girlfriends super-hot daughter
who'd we'd known to have boyfriends was involved sexually with Diane, and was either -bi-sexual or
had since determined she was a lesbian. This didn't bother me, especially given the scene I had just
witnessed that took my breath, and maybe a half-gallon of sperm away. That was without a doubt at
the top of whatever else I had ever experienced erotically, and my cock immediately became hard again
just thinking about it. I turned off the reading lamp, and stroked myself to another mind-blowing orgasm,
and fell asleep after deciding not to discuss anything with Cindy regarding Jen.
The next morning I got up late, and I went to the kitchen when the smell of fresh coffee permeated the
house. When I got there I smiled and said "good morning, ladies - I didn't expect to find you here".
They were both kind of stunned and Jen sheepishly asked me when I got back. I told her late last
night, that I was so tired I just dumped my computer downstairs in the office, and went to straight
to bed. They sort of brightened up and didn't ask how late, and I wasn't offering any more information
so I changed the subject.
We had a nice breakfast, and after grabbing another big mug of coffee announced that I was going down
to my office as I had a ton of work to do. After a while, Jen called downstairs, said she was taking Diane
home, and would be back after classes. I called back that I'd see her later and as I got back to work, my
phone rang, and it was Cindy telling me she'd be home around 9:00 that night as her flight got cancelled.
I told her fine - I'd make dinner so she'd have something to eat when she came home, and if she called
me before she got home I'd meet her at the door with a glass of bourbon in hand. I heard a loud and
happy sigh on the other end of the phone and heard her say "I am SO looking forward to THAT… I knew
I picked the right guy - I'll see you when I get home. Love you…". I said "Me, too - later babe" and hung
Later in the afternoon, Jen came home. She called for me, and I called back that I was reading on the patio
when she came out with a few drinks (a strong glass of bourbon for me). I told her that her mom had called
and wouldn't be back until 9:00 or so, while noting her light, form-fitting sweater (evidently braless), black
leggings, and pretty feet with nicely manicured and polished toenails. Gad, but this young woman knew how to dress in a way that could arouse a dead man, and I had to sort of readjust myself to keep from exposing the fact that my cock was starting to harden. So just chatted about general stuff, my business trip,
her classes and so on, but eventually she came out with "about last night…"
I played dumb looking to see where this was going and asked "what about it?". Then she looked me
straight in the eyes and asked "exactly when did you get home?". I said "I'm not entirely sure, but it was
sometime after 10 or so, why?". She said "come with me, and bring your drink" and we went inside. I put
my stuff down and followed her down the hall when we came to her room, and she pointed to the now dried
semen on her rug, turned to me with a little smile, saying "you saw me with Diane last night didn't you?".
I nodded in the affirmative. She turned around and led me back to the living room, saying it was handy that
her mother was coming home late so we could clear the air.
So we sat on the sofa and started a more ernest conversation, with her saying that she'd gotten up after she
and Diane finished, and almost had heart failure when she stepped in the wetness on the floor and
recognized it for what it was. So here we were both somewhat guilty, she explained: her for having a
sexual relationship with Diane that they had both kept hidden from their friends and families, and me for
having watched them and leaving a pile of squirt on her carpet. Hence - since all exposing either of us on
the part of the other would likely cause is a serious ruckus with no good outcome, it would be best for both
of us to just keep it between us. I agreed, and apologized for leaving a mess on her carpet, but admitted
that I'd be lying if I didn't enjoy watching them.
And then she started telling me about how it all came about.
Jen said that she and Diane had gotten drunk at a party soon after both of them had been either been
broken up with or had left their boyfriends, and shared a taxi to Diane's place when they determined they
were both too drunk to drive home. When they got to Diane's, her roommate had left a note saying she
went home early that week due to family issues, so the two of them sat down on the sofa and started
smoking pot. Apparently, they had gotten into "shot-gunning" each other, blowing smoke into each others
mouths. Then Jen continued telling the story.
As they caught even more of a buzz, they got closer to each other when Diane, who was kneeling towards
Jen lost her balance while blowing smoke into her mouth and ended up planting her lips on her. They
finished the shot-gun of the moment but froze when their lips met with mouths opened as Jen accepted the
smoke from Diane. Their tongues met and in an instant their frustrations with their boyfriends, lowered
resistance because of their partying, and horniness all hit at the same time. Immediately they were kissing
hard and deep, clinging to each other, beyond caring. They were soon rubbing their bodies together and
Jen said she remembered getting super wet and hot as both of them became turned on to each other.
Diane had pushed Jen back onto the sofa and was on top of her when she reached up and rubbed Jen's
nipple between her thumb and forefinger through her top - sending bolts of electricity through her body.
At that point she knew they were having sex for and nothing was going to stop it.
Jens knee rose up between Diane's legs, and they ground themselves together. Diane suddenly pulled
back and pushed herself up and looked at Jen. Then with an instant and mutual agreement, they both got
up and ran to Diane's bedroom, hand in hand where they ripped each others clothes off and made love all
night long. They've been together ever since, and while they both date occasionally (they both like
boys/men just fine), they will otherwise be Lesbians Until Graduation (LUGs). I told her not to worry about
it - if there was going to be an issue it would be between her mother and her, but certainly not with me.
She then sheepishly said that she needed to admit something as well. I asked her what she meant by that,
and she told me that the first night I spent with her mother, she heard her mother's moans and cries when
we were in bed and she had come home early. We had also left the door ajar, and she had watched us
for an hour, and got herself off as well - so now we're even!
Jen then said "you know, in a weird way, I'm kind of relieved this happened. I haven't had anyone I could
confide in about any of this… My mom would probably hit the roof."
"Well,", I said, "we don't have much left to hide from one another now do we?". She laughed and
agreed. So I slapped her on the knee and said "C'mon, you can help me make dinner". So we went to
the kitchen and started cutting stuff up, had a few drinks and just enjoyed each other's company. Not too
long after dark, I got a call from Cindy saying she was almost home, and I told her that dinner was just
about ready so her timing was perfect. I poured her a stiff drink just as the taxi pulled up, and handed it
to her as she walked in the door. We clinked our glasses together, took a good pull off of them, and I kissed
her deeply. I had been anticipating her return and was seriously horny. But for now I knew it was wise to
wait, so I took her bags from her and carried them to the bedroom as Jen called out ("Hi mom!") to greet
Cindy home. Cindy followed me and shut the door behind us and was taking her business clothes off
before I put her bags down. I turned around to watch her and sat on the bed as she kicked off her
shoes, and smiled at me whilst I watched her undress hungrily, and I felt my cock hardening. Now nude,
she walked over to me and pushed me back on the bed and climbed on top of me and planted her lips
on mine as I stroked her back.
She got up, and said "I've been SO looking forward to this… But Jen is waiting to see me and I hope you
don't mind if we save this until later." I told her I didn't mind, but she reached down and unbuckled my
pants, unzipped my fly, noted the pre-come wetness of my boxer shorts, pulled them down and sucked
my prick into her mouth. I gasped and said "I thought you wanted to wait" and she looked up smiling, and
replied "thats just to give you something to think about". She went back down on me, worked my shaft over
with her tongue, swallowing me almost whole for a moment, and then got up and said "let's go have
dinner" as she pulled on a set of sweat pants, a t-shirt, and finished off her drink.
We all had a great dinner together, and after chatting about the events of the week (with a few topics
excluded) watched a movie together. Eventually we decided to call it a night and Cindy and I retired to
our room, where we pulled off each others clothing, kissed deeply, fell onto the bed, and settled into a
beautiful and extended 69. We made love for a few hours and fell into blissful sleep in each others arms.
Eventually, as a new sales region was being created and Cindy had to spend a little more time away on
business, Jen would spend some more time at home often with Diane coming over. The two of them
looked so cute together, and as Jen revealed to Diane that I knew about the two of them and was cool
with it, they soon openly showed affection to each other in front of me. Since Jen and I always saw
each other at the pool in our bathing suits, and now at home as well (not to mention, completely naked,
Jen had started to wear even less around me and occasionally only wore a t-shirt and nothing else, but I did
notice that she was starting to lose her completely clean-shaven look in favor of a large triangle over the
top of her pussy. I had to ask her to wear just a little more, as otherwise she was really becoming a
distraction - much to her amusement. But she and Diane, when staying at the house when Cindy wasn't
home, would both walk around wearing very little. While this was going on I had to learn to position my
cock so it wasn't obvious that I was as stiff as a board. Nonetheless, I was accepting the "sacrifice" of
my boner discomfort in return for seeing two young women strolling around the house with very little
clothing on (otherwise, I might as well turn in my "guy credentials").
As Diane became comfortable with me being around when she and Jen were there, it became a common
event for her to spend the night. Occasionally, I would hear a moan coming from Jen's room, but they
were a lot quieter than they had been that first night I'd seen and watched them (sadly). Once in a while
I'd pass one of them in the hall going to/from the bathroom, and would catch the fragrance of pussy as
they walked by.
Eventually, the winter settled in, and Cindy was still having to travel, albeit not quite as often as before.
But during the winter, travel becomes more unpredictable due to weather conditions, and living in the
frigid north east added to that potential.
During Christmas break, Diane went to visit her parents, and I'd noted that I hadn't seen her quite as often
and asked Jen about it. She looked at me, sighed, and said that Diane had met a guy, which meant their
time together had become more limited. Diane's boyfriend had made disparaging remarks about girls
having sex with girls, and though she wanted to continue having sex with Jen, they now had to be a lot
more careful. Anyway, the weeks passed and she still came over, but only occasionally to spend a night
at a time when Cindy was away, and her boyfriend was otherwise occupied. I asked Jen why she didn't
find herself a boyfriend, but she sort of shrugged and said that "the boys at school didn't really interest
her that much, they lacked maturity, and most of them had sold out to the frats..."
After Christmas and New Years, Cindy had to make another trip out west, and said she would be back
late on Friday as they had a early dinner meeting - and she had to take the last flight home. She texted me
Friday at lunchtime and said "don't wait up for me - I won't be home until after midnight - I'll meet you
in bed :-)". I sent a message beck to her "can't wait - see you later…", and went back to work. I was
heads down most of the day (let alone week), and hadn't been watching the TV or the weather. I ate
dinner with Jen, we watched a movie, had a few drinks, and I fell asleep on the sofa. When I woke up
I got up and wandered off to bed where I read a little while and fell into a deep sleep.
Sometime late that night, I felt movement on the bed, and while half asleep felt that familiar body snuggle
close to me. I reached over and felt the wonderful shape fold itself into me, as my hands stroked the body
cloaked in the sheer nightgown that I'd seen and removed so many times. I felt the heat emitting off her
body as I ran my hands over her breasts and felt her nipples sticking out. I whispered "I'm so glad you're
home…" and heard a moan as I stroked her. I moved my hand down her torso, and eventually between
her legs, which parted as my hand cupped her pussy. I inserted my middle finger into her pussy to stroke
up and touch her clitoris, and found her to be soaking wet and very hot. She gyrated her body and pussy
to accept my fingers as I continued to stroke, and my erection quickly built. I pushed my cock down
between her legs and under her ass, and used it to stroke her pussy from behind while I kissed the back
of her neck and rubbed her clit. I felt goosebumps come up over her body as her breathing rate increased.
Given how wet she was, and now that I was fully awake, I pushed her shoulders forward and pulled myself
back a bit. Noting how wet my cock was, the head quickly found her opening, popped in, and I started
pushing into her. She responded with a low groan as my cock entered her. She was already squeezing
my shaft with her pussy muscles as I entered her, and I could feel her body trembling as I bottomed out
and let my cock bask in the sensation of a hot and wet pussy. We slowly started moving together as I ran
my hands down her back and I thrust into her. The smell of sex permeated up through the blankets as
her body responded. I grabbed her hips and started slamming her from behind, when my cock was
clenched by her pussy, her body shook, and my balls were bathed in a large quantity of cum.
I pulled her over to me, and she flipped her onto her back, and opened her little gown. I started running my
tongue and lips over her body, from her ears, to her neck, down to her nipples, past her torso and traced
the triangular strip I loved to the top of her pussy. I circled the tip of my tongue around her clitoris, and she
pushed her pussy up to meet me. I pulled her clit between my lips and sucked on it as her hips started
gyrating. The musky smell, while a little different, was complimented by a larger than usual wetness, so
it seemed to me Cindy was especially happy to be home. I lifted myself up on my arms and moved between
her legs, which opened wide and up to ensure easy access. She reached down and stroked my cocked
a few times and positioned it to her opening, locked her ankles behind my ass and drew me into her as she
pumped her hips up to meet mine. Her pussy was so wet, so tight, and so hot that it seemed to surround all
of me as I drove it into her cunt.
Once I bottomed out, I began moving in and out of her, gradually building speed until our bodies were
slapping one another, my balls colliding with her pussy as I bottomed out, and getting drenched by her hot
pussy juices. Given how turned on she obviously was, It didn't take long for my balls to boil, and I tried holding on for as long as I could, but finally the need to seed her overcame my ability to endure any longer,
and I released several loads of sperm into her womb. I groaned in pleasure she came hard, thrashing
below me as her pussy squeezed every drop possible out of me.
I collapsed on top of her, and we kissed. Something was different, as Cindy wasn't giving me her entire
tongue as she usually did. I rolled off of her onto my back, and she started to lick and kiss my body as
she worked her way down to my semi-hard cock. She ran the tip of her tongue around my balls, and
up my shaft, and grasped my cock with her hands and started jacking me off as she licked my dick.
I was immediately startled, as this was something Cindy had never done before, and I reached over and
hit the button that turned on my reading light. Even without my contacts or glasses, I was stunned to see
Jen - NOT Cindy - look up at me as she sucked my cock deeply into her mouth. I pulled out of her as if I
was struck by lightning, and practically yelled "Jen! - What the fuck are you doing here!?!", and pulled the
covers of the bed over me by instinct, as if that made any difference at this point. Jen smiled at me, and
said her mother called earlier and said that her flight had been cancelled due to weather, and she'd
try to get the first plane out in the morning. I sternly told said "that isn't answering the question I asked"
and she replied "I wanted to fuck you since I looked in and saw you fucking my mother… I told you I'd
gotten myself off months ago when I saw you together - what I didn't tell you was that I was imagining
what it would be like to feel your cock sliding in and out of my pussy. And now I know…".
I remained stunned as she shamelessly pushed herself up, walked on her knees up towards my chest, and
sat on her ankles with her legs spread and pussy gaping at me. Her hair was resting on her shoulders
falling down to her just the top of her tits (just like her mothers), her pussy hair trimmed into a slight
triangle (just like her mothers), and she was wearing her mothers little night gown, though it was open
to fully reveal and show off her body, and she was smiling at me.
I couldn't believe it - I said "you… *planned* this." And she said "yes", and continued. "I'd wanted to
fuck you for a long time, but was discouraged when I started to wear less and less around the house,
and you asked me to not wear such revealing stuff. I knew you knew my mothers body, so I grew my
pussy hair out and trimmed it back so that it was just like hers. When she called and told me she
wouldn't be home tonight, you were working in your office, so I snuck into your room and took her
favorite nightgown. I knew she wasn't expected to come home until late, so when you went off to bed
I gave you time to fall asleep, and then entered the room quietly, moved a few things around for good
measure as if she had just come home, and slipped into bed with you. You did the rest.".
"I did the rest? - You didn't announce yourself! You didn't say anything! You were wearing your mothers
gown, what the hell is going on in your head?", I said. She replied "you got excited, ran your hands all
over me, and fucked me. Twice. You licked my pussy, kissed, touched, and tongued my entire body,
and came inside me… Look: your cum is dripping out of my pussy!". It was. I did. She inched forward
with her legs still spread above me, smiled and said "are you trying to tell me you didn't enjoy it? Hmmm.
let me check here…" and she reached down to my feel my cock through the covers, which was again
hard as a rock. "I see how angry you are… You're so angry that your cock is in serious need of some
attention, and I'm here to give it all the attention it needs. Look at how wet my pussy is. I'm SO turned
on by being in bed with you, partially because I know my mother would KILL me, but also because I
liked watching you pull your body through the water. When I first saw you and didn't know you were
so much older than me I was already attracted to you. No one was more surprised than me to see
greying hair when you pulled your swim cap off. But that night I thought maybe you'd be right for my
mom, and as it turned out, I was right - and the added bonus is that she's very happy…"
"However, you then went and disguised yourself and climbed into bed knowing what would happen,
and you would do this to your mother, who's happiness you're now touting?" I said? "How do you
justify THAT?" I asked.
"Simple. I was seriously horny and Diane isn't available. I borrowed you because mom isn't home.
It's cold and nasty outside, and I wanted to feel a hot cock inside me - yours in particular. I figured
out a way to make that happen - despite my efforts I knew you wouldn't make the first move, so I did.
Regardless, here's the bottom line: you've already fucked your girlfriends daughter, and she wants
more, so whats it going to be?", and with that she started massaging my hard-on, and reached over
to push the covers back at the same time. "You want to fuck me again, don't you? I've seen how
you look at me, and at Diane when she was here, or when the two of us were together. I knew how
turned on you were when you watched us - the evidence was obvious." She then let the nightgown
fall off the rest of the way...
My mind was saying "NO WAY" and my cock was going crazy as she massaged it and finally pulled the
covers to fully expose me. She rose and straddled me as she detected weakening resolve on my part,
and then in one motion ground down and impaled herself on my cock as her eyes rolled into the back
of her head. She gave me a lewd smile, and said "don't' look now, but you're getting fucked by your
girlfriends daughter… again." Jen started moving up and down as I watched her tight pussy lips
wrapped around my cock as she pulled out, and heard her groan as she slid it back in. Soon her
pelvis was gyrating as her pussy leaked juices all over my balls and the sheets. Her body suddenly
stiffened and shuddered as she came, and a torrent of cum came out of her pussy. She collapsed
on top of me and kissed me, but now her tongue fought its way into mine, and I could feel her
exploring my mouth with her tongue, as her hands roamed over my body. She now sat up and continued
caressing me as she pulled out of me, and inched her hips towards my chest. I could feel her pussy
leaving a trail of wetness up my torso, when she finally lifted herself up and straddled my face,
settling her pussy on my mouth and said "please eat me…" as my tongue stuck out to taste her, and
my hands cupped her ass.
My tongue slid into her, and worked her pussy using every technique at my disposal. I looked up at her
and she was squeezing her nipples as her body responded. Soon her hips were moving with my tongue.
When I pulled her clitoris into my mouth and sucked hard on it, she moaned lustfully and came in my mouth.
She lifted her leg and moved off of me, and started lying next to me on her side when I pushed her on her
back, straddled her face and stuffed my cock into her mouth. She sucked it hungrily, and soon I started to
fuck her mouth, with my hips, as my hands controlled her head. I was now really turned on by the
shameless horniness of Jen, knowing that I was having sex with a girl easily young enough to be my
daughter. Just as I felt my orgasm coming, I pulled my cock out of her, quickly moved between her legs,
lifted themhigh and stuffed my shaft into her pussy. I reached down and held her ass with one hand and
used it to time my thrusts into her wet cunt. I watched her breasts jiggle as I slammed into her body and
she groaned with raw lust, feeling my balls slapping her pussy.
My orgasm came up fast, and I pumped my load into her as her pussy nipped and grasped at my
cock. I held her there as she pumped me a few more times, and shrieked as she came one more time,
soaking my balls - again.
I pulled out, breathing heavily, and lay back on the bed. She turned to me on her side, and lifted
her leg over mine. I could feel her wet pussy against my leg as she put an arm over me. I looked
over the bed, and it now had several large wet spots on it that hadn't been there before, so clearly the
linens were going to have to be washed before Cindy came home.
I muttered "you're a naughty, naughty girl" as I felt her breasts brush my arm. Jen giggled and said "maybe,
but you didn't seem to mind taking advantage of it… Do I deserve a spanking?". So I slapped her on the
ass and she yelped. "Don't do that again, or it'll be worse next time" I told her. She whispered "I hope
thats a promise..."