Events during first serious relationship, post-divorce
It Started At The Pool - Part 3
I you haven't read the first two installments, you might want to do so to get the background of what
has transpired with Greg, Cindy, her daughter Jen, and her friend Diane.
Part 3 finds Cindy justifiably concerned about her daughter's confessed attraction/desire for Greg.
Jen is back in school, and Cindy's been home for a month and things have largely returned to normal.
However, a new complication has arisen with Cindy's next business trip, because she's been asked
by her company to stay away for an entire week, including a weekend. Cindy finally told him about
what transpired between her and Jen, and is concerned enough about her upcoming trip to consider
leaving her high-powered job to protect her relationship with Greg - from her own daughter.
To Take a Trip.
Cindy and I went to the kitchen and poured ourselves a few cocktails, decided to sit in the living
room, enjoy our drinks, and determine what we wanted for dinner. Jen was already on the sofa,
reading with her feet up, under a blanket. She smiled at us as we came to join her, and made room
on the sofa for us. When her mom turned away Jen looked at me and stuck her tongue out playfully,
and then went back to reading.
We started to think about what we wanted for dinner, and as the discussion went on we determined
that we all wanted something different. Hence, we decided to go out for dinner. I went off to see
about making a reservation at one of the Italian places in town, as the women hung out in the living
room. The first reservation I could get was for a few hours out, and it would only take 20 minutes to
get there, so we had some time.
I walked back into the living room, and the two of them went silent. "Everything ok?" I asked. "Yes"
came the reply in unison. "Great - our reservation isn't until 8:00, and that gives us an hour and a
half before we have to think about leaving, so I'm going to head down to my office and check on my
email, and read up on a few things", I said. "Ok" came from the two of them so I grabbed my drink and
I was just finishing up with some correspondence when Jen showed up at the door of my office. I turned
to see her leaning in the doorway. Jen was wearing a nice skirt that accented her curves gracefully,
and I was pleased to see her dressed like a woman and wearing stockings (they were casual, but nice).
"What can I do for you?" I asked.
Her looked instantly changed to that of a lusty vixen, and she opened her mouth and ran her tongue
around her lips as if she was working over the head of a dick, and then said "there's something I'd
like to do to you…". I sighed at her and said "Did you know you're mother is upset enough at you to
consider leaving her job so she won't have to travel anymore?" "Yes" she replied "she just told me."
"And how do you feel about that?" I asked her. "Like an idiot", she said, "If she quits her job, and is
home all the time, then it'll be difficult to…", and then she lifted her dress to show me she was wearing
high gartered stockings under her skirt, without any panties. My eyes were instantly riveted between her
legs (my god, she is beautiful, and such a slut!), and when I looked up she was smiling. I told her "cheer
up, you can still do that, but it would then likely be without my involvement. You'll have to either find a
boyfriend, or otherwise continue with Diane, or find some other option. Where's your mother?".
"She went into her office (one of the unused upstairs bedrooms) to make some phone calls." she said.
"So she told you that she was going to consider leaving work because of you - how did you respond?"
I asked. Jen replied, "I told her that she shouldn't worry about it, that I'd be away at school most of the time,
and that I had another interest anyway". "Oh? What interest is that?" I asked. "Diane, but I certainly didn't
tell mom. I think she'd hit the roof" she replied. "Ya know, at this point, I think she might be almost relieved,
because that would lift a lot of pressure from her", I told her. Jen looked at me, clearly unimpressed, "I am
not in love with Diane. I enjoy having sex with her, and she clearly enjoys sex with me, but you might recall
she did sort of leave me for a boyfriend, and I don't see how I can love a woman romantically. For that I
need a man - I had never been attracted to women before Diane and I got loaded and carried away with
each other. Where I really like her, and think she's beautiful, I think what I like about her is that her body,
in many ways, looks just like mine. We're about the same size and can virtually fit into each others clothes -
its almost like having sex with myself. I do love her, but thats as a friend, albeit a very, very close one".
"So, do you find other women attractive?" I asked. "I don't know. I do notice them and I suppose now that
you ask I measure them against myself more carefully. Maybe I do. But I have no interest in them
romantically." "Fine, so has your mother decided what she's going to do about this trip?" I asked. " I think
she's mulling it over" was the reply, adding "when I told her I had another interest she looked relieved, and
wanted me to tell her about it. But for obvious reasons I couldn't go there, and told her it was someone at
school, which is true". "All right, why don't you head back upstairs and study or read before we go, as it
won't help your mother if she finds you alone with me", I said.
I turned around to my computer to end the conversation, when Jen said "Greg?", and when I turned around
there was Jen, smiling, bent over with her skirt up, legs wide, perfect ass and pussy exposed, with a finger
buried to the knuckle in her pussy. "Go!" I said. She straightened up, smiled over her shoulder, and headed
up the stairs. I sat there with my brain in a turmoil with what I had just seen. Now its true that I had seen all of
her before, but now I hadn't seen her naked in a month, and seeing this young, tight-bodied near
nymphomaniac exposing herself to me caused tremors in my brain and crotch that shook me to the core.
Certainly, I got to see her extraordinary mother (who easily fit into her daughters clothes), who was in
outstanding shape, had a high sex drive, and internal muscles that made my innards jump when she squeezed me, all the time. But variety is supposed to be a good thing. In theory anyway.
My mind stirred on this topic for a while, and soon it was time to leave, so I shut down my computer and went
upstairs. I added a freshener to my drink and strolled into the bedroom, where Cindy was already putting
street clothes on, and she seemed kind of buoyant. She was standing with her back to me and saw me in
the mirror and softly sang out "hi sweetie". Then she pulled her sweatshirt off and bent over at the waist,
which (as usual) took my breath away. I walked up behind her as she reached for her bra and held her
close, and gave her a lingering kiss on the back of the neck, which visibly brought up goose bumps all over
her, and walked over to my bureau to select some clothes to wear. I took off my clothes and was putting on
some slacks when Cindy came over to me from behind and held herself to me, kissed the back of my
neck, gave my cock a quick squeeze and smiled at me as she walked out of the bedroom, grabbing a set of
pearls on her way out. I finished dressing and followed her into the living room, where Jen was wearing the
same skirt and waiting for us.
We went to dinner, and were seated in a small corner booth, Cindy on my right and Jen on my left. After
ordering a round of cocktails and a bottle of wine (to have with dinner), Cindy excused herself and went to
the powder room. I was sipping my drink when Jen reached over, ran her hand up my leg, and squeezed
my dick the second Cindy was out of sight, and I almost spilled my drink. "Jesus, don't do that - we're in
public!" I whispered. She just smiled and whispered back "no one can see - the tablecloths are too long".
"How does that matter? if your mother comes back and finds me hard she's going to wonder why" I
whispered back. "Really? Are you telling me she'd check you in a place like this? Does she do things
to arouse you in public?" she asked. "Thats none of your business" I whispered back. Just then I
brushed my salad fork off the table with my elbow, and it landed between us on the upholstered bench of
the booth. I reached down to get it, when Jen got it first and took it away before I reached it, and moved
her hand between her legs. I reached for her hand, but she took mine, pulled it between her legs, and
held it to her bare pussy, and I could plainly feel her excitement.
I retrieved my fork from her hands as she was laughing, but only after she'd smeared my hand with her
wetness. I put the fork back in its proper place on the table, caught the aroma of "Eau D'Pussy" on my hand,
gave Jen a frown and got up to head for the men's room just as we saw Cindy on her way back to our
table. While I was working my way out of the booth, I'd managed (much to Jen's amusement) to reposition
my now hard cock so it wasn't as obvious and headed for the washroom, with my sport jacket buttoned.
As Cindy and I passed each other, I turned to her as I caught her eye and she smiled at me. I returned her
smile, and ran my eyes up and down her figure and gave her a friendly but very quiet "I want to bounce your
bones" kind of grunt as I went on my way. Once in the washroom, I scrubbed my hands thoroughly, allowed
my hard-on to subside, took a leak, and washed my hands again.
Dinner was great, and finished uneventfully. We went home, watched a little tube, and went to bed. I
got in first, and held the covers open for Cindy as she slid into bed with me. She was wearing only a
very sheer silk night-shirt that hugged her figure. She lay down next to me (I usually sleep naked) and
the feeling of the silk and her warmth was really nice. I rolled onto my side, and traced the contour of her
body with my fingers. She reached over and pushed the light switch, leaving only a small reading lamp
on, and then turned over and pulled me to her. We kissed deeply and calmly, and ran her hands over me
as she reached for my now partially hard member, and whispered "I was aroused by how you looked at
me, along with that little grunt you gave me at the restaurant." "You arouse me" I answered back. She
pulled away and turned to her nightstand, pulled a bottle of lube out, and applied it to herself. She then
rolled me on my back and pulled her nightshirt up, straddling me. She took my almost-hard cock in her
hand and rubbed it against her pussy as she kissed me, slowly taking me inside of her. I lay there with
her on top of me, feeling her inner muscles as they flexed and massaged me. She started slowly moving
herself along my shaft and I could feel her breasts and nipples rubbing against my chest. I looked at
her and she had her face up and eyes closed with a look of serene pleasure on her face. I rolled her
over, taking care to stay embedded, and slowly took her to the moon. When her orgasm arrived her body ,
shuddered and grasped and squeezed my cock, and I came a few seconds later. We lay together, as all
was right with the world in that moment.
Cindy got up to get a glass of water, and as she walked away I could see the telltale evidence of our
activities on the back of her nightshirt. She was out the door before I could say anything. I heard her
and Jen in the hall saying something, and she was soon back in the room with glasses of water for the
both of us. After a few sips, Cindy hit the button for the nightlight, and as I was lying on my back, she
draped her arm over me and nuzzled my neck. I put my arm over her so she could rest her head on
my shoulder. Then she whispered, "Jen told me she's found a new interest at school". "Really? what's
that?" I whispered back. "Who that is is more like it, and thats more important" she said. "Oh... did she
elaborate on who? Who's the lucky guy?" I asked. "She didn't say, but apparently its someone she's
known for a while. Perhaps I don't need to worry as much as I thought, now that she has a new
distraction" she whispered. "So have you decided what you're going to do?" I asked. "Well, if she starts
spending weekends away from home with any regularity, I'll know she's fully occupied, and I'll feel safe"
she said. "What are you going to do with this trip they want you to take?" I said, "thats coming up pretty
soon isn't it? You'll have to make travel plans, and so on."
She whispered back "they made arrangements for me to go, but if I'm going to pull out I'll have to do it
soon." "Whatever you feels best. I certainly love it when you're here, but where my career allows me
to mostly be around home, I accept that you have a life, a career, and your priorities. I can't decide
that for you - and unless you ask me for an opinion I'm only here to listen and support you" I said. Cindy
whispered "I know and appreciate that. So I"ll ask you, what do you think I should do?".
Damn it. Me and my big mouth! I opened myself up to this. So I thought about it and told her "You've
got to do what you feel is right inside. I'm old enough to take care of myself". "But would you be able
to stay away from her if she did something aggressive? Do you find her attractive?" she asked. "Do
you mind if I turn the light back on?" I asked. "No, why?" she asked. I turned the light back on and
picked up the photograph of her and Jen together that was taken in the summer, that showed them both
to advantage, and showed it to her.
"Does this answer your question?" I asked. She looked at it and asked what my point was. I poked her in
the ribs and smirked at her and said "that is the point. You aren't looking very hard. My dear, I admire
your brains and your beauty, but this is one occasion where I'm at a loss as to where your powers of
observation went. I'll keep this simple: the family resemblance between you and Jen is astonishing.
She obviously is her mother's daughter, you have the same hair, same body shape, and you might
recall, that I called you Jen when I met you at the pool. I thought you were her, right? You fit into her
clothes and she fits into yours. Lets be realistic, if I didn't find her attractive, how could I possibly be
attracted to you? I wouldn't be much of a man if I weren't acutely aware that she's a lovely young lady,
would I? And I know you're proud of her and would think I was insane if I somehow thought otherwise.
Am I wrong?".
"The family resemblance thing is obvious - people have told us both that before. Sorry, I'm so used to her
that I don't think even about it, and you pointing it out to me makes me feel a little foolish. I'm slightly
taller than she is, but if you couldn't see you might not know the difference", she said, and continued
"But I know what I can do, and I've been thinking about it - I'm going to cut my hair shorter". "What will
that do?" I asked her. "It'll be easier to take care of, it'll dry faster, and there'll be no mistaking the two
of us" she said. To this she had a point, and her previous statement certainly hit the nail of the head.
We both went to work the next day, and I got home earlier and she'd called to say she'd be late for
dinner. So I put something together and when she walked in my jaw dropped to the floor. Cindy had
gotten her hair cut short enough so that it was over her shoulders, accented her beautiful neck, and
framed her face in a way that made her look… elegant. She looked at me and said "what do you
think?", and seemed concerned. I stared/leered at her up and down. I walked over to her and turned
her around slowly so I could properly observe the whole view, quietly whispered "woof!" just loud
enough so she could hear it, proceeded to kiss her tenderly up and down her unobstructed neck from
behind and exhaled my hot breath into her ear, wrapping my arms around her. "You're hair isn't long
enough to conceal the hickies you're going to have all over your neck by the time I'm done with you"
"Then you're just going to have to control yourself" she said, obviously pleased with my reaction, "and
if I find myself with any hickies you'll have to grow eyes in the back of your head". Hmm. Where did
I hear THAT before? "I decided to do the trip" she said. "What? Really? What made you decide that?"
I asked. "Two things: one, I think I procrastinated too long and If I were going to pull out I should've
done it earlier - to do so now wouldn't be professional; two, I'm more at ease since Jen has this new
distraction, and I'm hopeful that will work out for her. Plus, she had mid-terms coming up, and a major
paper due so she'll have to apply herself more".
So Cindy left on her trip the next week, and she already made arrangements through work for us to
go to Bermuda on the company's dime during what would be Jen's spring break. Alone.
I ran into Jen in the pool a few times before her mother left for Dallas, and she showed up with a new
swimsuit. It was still designed for lap swimming, but it was a bikini style one that showed her toned
figure to advantage. It was a beautiful thing to watch her body move through the water. Some guy
who couldn't swim under control joined her in her lane, and while thrashing around almost collided with
her, so she moved from that lane over to mine. We finished up our workouts and ended up in the spa,
and chatted. She was working on her exams, but had finished her research paper. Her roommate
had recently taken to "sleeping" with her new boyfriend in their room, and were keeping her up at night.
She'd complained to her roommate who told her to mind her own business. Apparently, when Jen
pointed out that since they were fucking barely three feet away from her, and that made it her business,
her roommate became angered and therefore made zero attempt to keep the noise level down, let
alone staying under the covers.
Early the next week, late at night, Jen showed up at the house. I was in my office chatting on the phone with
an old friend, when she came to the door, looking exhausted. I wasn't expecting her, and was a bit jolted to
see her standing there. "What's wrong, why are you here?" I asked her. "I can't sleep, and Donna (her
roommate) is simply out of control. She brought not only her boyfriend over, but some friend of his for a
threesome, and then they demanded that I join them. I went to the RA, who's going to try to find me another
place to live, but in the mean time I can't sleep, and despite the commute being a lot longer I'm better off
here. I hope you don't mind" she said, looking very unhappy. "By the say, where's mom?" she asked. "She
went to Dallas" I replied. "She didn't tell me she was going… And for that matter, neither did you" said Jen,
but she was now smiling. I told her to either go study, or to bed. I had a few things to finish up before I turned
I eventually wandered upstairs, and went to bed. And soon, there was a rustling on the bed and she was
there. Naked. I felt her hands run down my body, cupping my balls. "I have to sleep" I murmured, "I've got
a lot to do tomorrow. Please go to sleep", and turned over. "You don't have to do anything, I'll do all the
work" she said, continuing "I'm going to give you a tongue bath you'll never forget, and the sooner I get
started, the sooner we can both get to sleep".
I groaned and rolled onto my back, knowing she was relentless and wouldn't give up. She whispered
"on your stomach" and helped turn me over. She methodically moved from my neck down my back,
kissing, touching, and licking me. I could feel her hot breath everywhere she went, as she progressed
down my body slowly. I knew tomorrow was going to seem to take forever, but decided to just lay there
and accept it for what it was. She gave me a pillow to put under my chest, and continued down my body
and legs, pulling the covers down as she went. Jen then turned around and straddled over my body on
all fours, rubbing her breasts and nipples all over my back, and ass. She squatted down and I felt the
obvious wetness of her pussy as she rubbed it on my Achilles tendon, while she kissed the backs of my
thighs and ran her hands up the sides of them. Soon there was a concentration of her working my ass,
and she started kissing and rubbing both cheeks, while she caressed my balls and pushed my legs
further apart for better access.
All of a sudden she parted my cheeks and buried her tongue into the crack of my ass, and ran her tongue
around my asshole. She poked her tongue into it and started rimming me aggressively as she rubbed
her pussy on the back of my leg. I was now fully awake and delirious, astonished at what a slut Cindy's
daughter was. She collapsed between my legs and worked my backside and balls, as she took them into
her mouth. She then got up on her knees, turned me over, and knelt down to lick the shaft of my iron hard
cock and take me into her mouth. She pushed herself up, allowing my cock to thump against my stomach,
when she straddled me and impaled herself on my shaft. Jen was soaking wet, and her pussy was hot
and very tight as she pushed herself down onto me, while her insides made room for my cock. When she
bottomed out I could feel her juices leaking out of her and down my balls.
She sat there in the pitch dark of the room, flexing her pussy muscles, apparently just enjoying the
sensation (or satisfaction) of me being embedded in her womb. Her body started to move up and down
my shaft slowly, when she leaned forward and clung to me, and I felt her entire body's friction while she
pleasured herself, grinding our pubic bones together. I ran my hands over her tight and hungry body, and
grasped her ass with both of my hands and helped move her. I ran a finger down the crack of her ass and
felt the wetness of her pussy on my fingers. She started moving faster and was groaning, when I felt her
insides starting to tighten. Her groans started getting louder and her her body trembled as her orgasm
built, and when her body stiffened I roughly dragged my finger up from the back of her pussy through her
ass crack and sank my finger to the knuckle into her asshole as she screamed and shook uncontrollably.
I could feel the rush of hot wetness that poured out of her, so I flipped her over and climbed on top of her,
and stuffed my tongue into her pussy and sucked the juices out of it. She reached for my still-hard cock
and sucked it in, savoring her flavor as she ran her tongue over the shaft. I pushed it down deep into her
throat, and she pushed me back up, trying not to gag.
I picked myself up and moved back around so that I was between her legs, and running my tongue up
her body. I brushed my teeth over her nipples as I brought her leg up on my arm, and felt for the
opening of her pussy with my free hand, guiding my cock. When I found it I lifted up and drilled into
her with all my weight. Jen's pussy tightened as her body convulsed, while a second powerful orgasm
shook her, and I continued to drill her pussy relentlessly. But my desire to screw her until she was dry
was overruled by my inability to resist the need to empty the contents of my balls, which pumped a
commanding load of seed into her loins. She shuddered again, and held me in place as her orgasm
(and mine) subsided. While lying on top of her, I could feel her heart beating almost out of her chest as
she tried to catch her breath. Her arms finally released me, and I rolled over, and off of her.
Jen whispered "that was fucking awesome…". I ran my fingers down her body, and she shivered. I
turned over onto my side, and said "go to sleep, slave". As I nodded off, I heard her whispered reply,
I awoke early the next day, pulled on my sweats, looked at the young woman lying in the bed, and headed
to the kitchen to make some coffee. I toasted and ate a bagel while the coffee brewed, and when it was
done I headed downstairs to my office. I quickly got into work, and started writing a report for the
executive staff, when I heard the water rushing through the pipes upstairs - apparently Jen decided to
take a shower.
I was heads down going through some correspondence when I heard her coming down the stairs, and
soon she was standing in the doorway of my office in a sheer robe, with her hair up in a towel, holding
a mug of coffee. I heard her say "mind if I come in?", I said "no" and she strolled in a pulled a chair over
towards my desk, and sipped her coffee. I was finishing off a message, when she put her feet up on the
desk. I reviewed the message, sent it on its way, turned to see her feet up on the desk, legs open, and
her pussy looking up at me. My eyes moved up her body, and then I noticed that she was pleased that
I scanned her body before looking at her. She put her coffee down, put her feet on the floor, stood up,
and shrugged her robe off her shoulders, let it fall onto the chair.
She stepped even closer to me, brought her hands to both sides of my face, and gently guided it to her
pussy. I could see her hooded clit, and her inner lips hanging just out of her. I removed her hands from
the sides of my head, and stood up, and guided her over to the table facing the wall near the door. I then
bent her over the table, keeping her legs spread wide and both feet on the floor, and told her to stay there.
I observed her muscular ass, legs, and perfect shape as she stayed bent over the table, waiting for
whatever I'd planned next. I slapped her ass, and she jumped, but returned to her position. I ran my hands
up her legs, over her ass, up her back, and enjoyed seeing her arch her back. I then brushed her pussy
lips with my fingers, to find them damp. I slowly undid my sweats and allowed them to fall to the floor, and
my cock swung free. I rubbed it up and down her bare pussy lips, and started to masturbate her clit with
the head. I took my time, and she started trying to push back to take me inside, but I commanded the slave
to be still. Every now and then I rubbed my cock along the lips of her pussy, and up over her asshole,
and squeezed the pre-cum out of it, making her ass and crack slippery and wet.
Eventually, I started to push inside her, which given the ever-building wetness, was evidently welcome.
Jen sighed when I penetrated her, and moaned when I slid it all the way in. I then pulled it all the way
out, lowered myself to my knees, and stuck my tongue into her pussy. Her body smelled fresh, and the
aroma of her pussy was intoxicating. I pulled her outer lips one by one with my lips, and then circled her
clit with my tongue before sucking it into my mouth. Her pussy was frankly wet now, and she was pushing
her ass back to me, trying to get more of my tongue into her. I stuck a finger into her pussy and got it very
wet, and circled it around her cinnamon ring. She squealed and pushed back as I ran my finger around her
hole. My finger slid into the first knuckle, and I heard her catch her breath, but she kept pushing back,
burying my finger all the way. I got up, leaving my finger inside of her, and slid my still wet cock all the way
to the hilt.
She started breathing harder, and I stroked my shaft in and out of her several times when I pulled it back
out and squeezed more pre-cum onto her other hole. I ran my finger around a few times as she pushed
back on it, and then pulled it out, and replaced my finger with the head of my cock, which was wet with
pussy juice and pre-cum. As I pushed on her she she pushed back, and the head embedded itself in
her cinnamon ring. I took some of the juice that was leaking out of her pussy and put it (with some spit)
around the shaft of my cock and pushed into her. When I was about half way I stopped and let her get
used to this new invasion. I stood looking down at my cock, embedded halfway into the ass of this young
woman, who had offered her body to a man more than double her age. She started to pull forward, but
then pushed back, and pushed back some more, and I felt her ring gripping the shaft of my cock as it
slowly bottomed out, and my balls were now mashed against her pussy.
The thought of being embedded so deeply inside her ass caused my cock to surge with strength, and I
pulled out a bit and then sank it back in. She started to move with me, and we started to pump together.
Eventually, our pace increased, and I felt my orgasm building. I reached down between her legs and
rubbed her clit with my fingers, as her wetness coated them. When I got to her love button she became
frantic, and squeezed my cock in a way that caused me to lose control and explode into her rectum.
I just stood there, trying to not let my legs collapse underneath me while I was rocked by a powerful
orgasm, and I pumped jet after jet of sperm into her. She came hard, and squeezed my cock clear out
of out of her. I fell forward onto her back, and stayed there catching my breath.
I slowly pushed myself up, and told her "thats enough of you for the morning". I picked up my sweats
and wandered out of the office, and headed upstairs. I walked into the shower, turned it on, and stepped
in. In a few moments, I saw Jen's naked shape through the shower doors, which then opened and she
stepped in. I was letting hot water run down my body, and she pumped the bottle of body wash, and
began silently scrubbing me. I let her bathe me from head to foot, and then she shampooed my hair.
As I rinsed she soaped her self down, and followed me out of the shower when she was done rinsing.
Then, she meticulously dried me off, and then dried herself off as I watched. She then dropped her
towel, walked slowly over to me, put her arms on my shoulders, held me close, and kissed my chest.
"Is there anything else I can do for you", she asked. "Yes. You can now go and do your studying like
a responsible young lady" I said, "because I've got to get back to work".
As it turned out, Diane and Jen were in a class together for the current semester, and therefore it made
sense for them to team up for a class project. Diane was having a harder time with her new roommate,
who liked to party and listen to music all hours of the day, when she preferred to study quietly (I found
these nuggets of info out from Jen while we were eating lunch).
I suggested to Jen that maybe the two of them should move in together, since they clearly got along well,
and had this "friends with benefits" thing going. Jen laughed at that suggestion, because she wasn't sure
either of them would get much accomplished. But I pursued the topic, saying that the two of them were
mature enough to ensure they were going to get the work done, while solving two problems at the same
time. With midterms coming up the next week, and roommates presenting problems for both of them, I
suggested that maybe Jen should see if Diane wanted to stay at our place.
Cindy was away until the following week, we had plenty of room, I was busy with two clients, and had
a lot to do. Besides, then they could commute together. Now, I didn't mention that I'd love to see the two
of them walking around scantily clad, etc, which to me would present an added bonus. Jen thought about
it and said she'd bring up the idea with Diane.
I went back to work after lunch, was promptly involved in a few conference calls, and then had to visit
my client downtown. So I suited up, got in the car and took off after telling Jen (who I was pleased to see
was deep in study) I'd be home late, as we were finishing the day with a dinner meeting.
My meetings went well, but I still got home late (around 11:00pm) with a bit of a buzz going, because these
clients liked to party, and the booze was flowing. I pulled into the driveway and saw Diane's car there,
which was a surprise. I walked into the house and the two of them were wearing their usual around the
house kind of clothing (not much!) from the looks of it, and were watching TV under a blanket on the sofa.
I said hello and got a cheery reception from the two of them, and went to my room and got rid of my suit
and stepped into a fresh set of sweats. I returned to the living room with a glass of water and joined them
on the sofa to watch a little tube with them before going to bed.
During a commercial break, Diane grabbed the remote and muted the sound, and thanked me profusely
for allowing her to stay. I told her I was glad to be of help, and asked them if they got any work done.
According to them they had made a lot of progress, and were just relaxing for a little while before calling
it a night. I watched about 10 minutes before I found myself dropping off, so I excused myself, said
good night, got in bed, and promptly passed out.
Sometime while it was dark, I found myself no longer alone in bed. Now its hardly a burden to have a
young woman with a toned swimmers body jumping into your sack, but this was a new and uncomfortable
twist. Giving credit to the department of the obvious, allowing others to know you're fucking your mother's
boyfriend isn't what one might associate with a good idea. "Jen, what the hell are you doing here?" I
whispered as she felt for me, when I realized she was naked and still smelled of sex (presumably because
she was having Diane as a midnight snack). "Diane knows about us, so whats the big deal?" she said.
"What do you mean she knows about us?" I said, "you told her?". "Yes. Why?" she whispered back.
"Gee, why don't you just invite her to come in and watch?" I whispered back to her. "Because she might
take me up on it" she replied, adding "she thinks you're pretty cute, and she was here once when you and
mom were going at it. She talked about it with me". "What do you mean she talked about it?" I whispered.
"Diane asked me if I was uncomfortable with hearing my mother getting laid", she said, "I told her it
made me horny, and I told her about masturbating at the door the first night you and my mother did it".
"Jesus, is there anything you two keep quiet about between each other?" I asked. "We do have sex
together, so whats the big deal? Besides, she thought that was pretty hot" said Jen. "Jen, did you tell
her about your sneaking into the bedroom when your mother called and said her flight was cancelled?"
I asked. "Of course. My mother's nightgown was her idea", she whispered back, giggling, "and, it
worked like a charm".
I was dumfounded.
"I grant you you were successful in that regard. By the way, I have a request" I whispered. "Whats that?"
whispered Jen. "I want you to arrange for me to watch the two of you having sex" I whispered. "What? I'm
not going to let that happen" she said, poking me. "Why not? You have no problem with me seeing you
naked now, and I've already seen you having sex with Diane. So what's the big deal?" I asked. "The only
reason you saw us was because you came home early and didn't announce yourself, and even then you
left 'evidence'" she said. "Yeah, so? You admitted standing at our door for an hour watching your mother
and I, and masturbated over that as well!" I replied. "But I didn't leave a mess behind, and the only reason
why you knew about that was because I told you" she said. "Ok, SLAVE, I require you to have sex with Diane and let me watch" I sternly whispered. "What? No way! I said you can make me do anything, but thats with you!", she said. "Bullshit. You didn't stipulate who with - you said and I quote, 'Anything. Any. Time', or don't you want that to continue?" I whispered, continuing "you can pleasure me orally while you consider that".
With that, Jen reversed herself so she was facing my crotch, and took me into her mouth. I could smell the
aroma of an aroused woman as she applied gentle suction while running her tongue around the head and
shaft of my cock. She started to run one her hands over me, and traced her fingers around my balls, rubbing
and fondling them, as she started to get into it and began to move her head up and down my shaft. I just
lay there and enjoyed being given wonderful blow-job by this sexually hungry young woman. As the sounds
of her ministrations grew, her aroma became intoxicating, so I reached over the ran my fingers between her
Jen was dripping wet, and her juices were leaking out of her onto the linens. She whimpered as I traced a
finger through her pussy lips. I ran a finger back and forth a few times when she got up on her knees, and
straddled my face as she continued pleasuring me. As she lowered her hips I took her tight ass in my hands and ran my tongue around her pussy as her body trembled. I had only given her a few long licks with my tongue and pushed it as far as I could into her opening when she exploded and gushed her secretions on my face. She released my cock from her mouth as she tried to breath and I sucked her inner lips into my
mouth, and she screamed into a pile of blankets. She tried pulling away but I held her ass in place as I
continued, and she came again. I released her, and whispered to her "you may continue". She regained her senses and started on me again, and it didn't take long before my orgasm built and I released a massive
load of hot semen into her mouth. Jen drank it all in, slowly released my cock from her mouth, and rolled
off of me, panting.
As soon as she calmed and reversed herself, she wrapped herself over me and I felt her heart pounding.
"That didn't take long" I whispered, and said "I think you're really turned on by the prospect of me watching
you and Diane. You've been wet before, but I've never known you to drip. Nor have you ever come so fast
when I stuck my tongue into you". Jen whispered "You might be right… The thought aroused me, but I'm
not sure she'd go for it. On the other hand, she's probably listening to us right now - she encouraged me
to come in here tonight. The thought of me with you really turns her on…".
With that, I quietly disentangled myself and moved quickly to the bedroom door, and the second I got to
the door (which was not closed all the way) and looked out, I saw and heard Jen's door shut in the dimly
lit hall. I walked back to the bed, hit the button to turn on the reading lamp, took Jen by the hand, and said
"come on". While she initially resisted, on the second tug she got up, and I pulled her towards the
door of the bedroom as she whispered "I don't think this is a good idea". "Bull", I said, "this conniving
nonsense on her part has gone on long enough". I guided her out of my bedroom, across and down the
hall to hers, turned the doorknob and gently pushed the door in, and then the naked Jen. I head Diane say
"I think Greg might've heard me…", which was all I needed to hear, so I walked in behind Jen. Diane's mouth fell open, as she tried pulling the sheets up to cover herself.
I took Jen by the hand, and we both slowly walked over to where Diane was sitting on the bed, trying to
hold the sheets up to cover her naked body. She was looking at me with huge eyes, and I saw them
darting between my semi-hard cock, face, and Jen. I took one side of the sheet, motioned for Jen to take
the other, and pulled it away. She initially put up some resistance, but then realizing that she had been
busted, she released her grip on the sheets and we pulled them away. Diane was sitting on the bed,
uncovered by any sheets, with her feet on the floor, but was trying now to cover her breasts and pussy with
her hands. I stepped closer to her, and pushed her back onto the bed.
"Wh-what are you going to do?" she whispered. "Jen, you know what I want to see. Get busy." I said. Without a word, Jen got down on her knees before Diane, pushed her legs apart, and gently moved Diane's hand away from her pussy. Her cleanly-shaven pussy's lips were distended, and were obviously wet. Jen leaned in and ran her tongue between the distended lips and up to her clitoris, which she circled with her tongue. Diane's eye's were now concentrated on me, as she was watched my cock grow into a furious hard-on while I watched Jen eat her naked pussy. The look in her eyes turned from concern into lust as Jen's ministrations had their effect, and she stared at my cock. Her arm and other hand gave up any attempts to cover her breasts as she moved her hands to hold Jen's head to her pussy and her hips began to respond. She quickly reached behind her and stuffed a few pillows under her head so she could watch, and then returned her hands to hold Jens head, and run her fingers through Jen's long blond hair.
My cock could wait no more, and I started stroking it as I watched Jen bury her face in Diane's snatch. Diane
was now moaning with lust, and grinding her pussy into Jen, trying to drive her tongue deeper into her pussy. Just then I realized that jacking off wasn't necessary, so I got on my knees and pulled Jen's ass up so she was on all fours, and slid my almost painful hard-on into her soaking wet cunt to the hilt. I let it just sit inside her and enjoyed the feeling of Jen's pussy muscles massaging my shaft as her juices soaked my sack. She started to eat Diane with even more energy than she had before, as I started to move my cock in and out of her. My brain was exultant - I was watching a beautiful young woman lustily eat out her equally beautiful girl friend while my cock was buried inside her. As I thrust into Jen, Jen was pushed into Diane's pussy, and Diane was tweaking her nipples while watching me fuck her girlfriend from behind with a look of animal lust.
This combination was too much for me. My orgasm built up and I tried to hold back. Regardless, my cock
released a torrent of hot cum into Jen's tight pussy, and she moaned as Diane's body shook and went limp.
My cock was still hard, but rather sensitive, so I left it inside Jen as her inner muscles gradually released me.
I pulled out of Jen, who then got onto the bed, straddled Diane's face, and sat herself down on it as Diane
stuck her tongue out to meet it. Soon, she had Jen slowly gyrating over her face as she sucked and drank my load out of Jen's soaking pussy. Diane's pussy was looking at me, and her legs were still open. I moved
forward and took her distended lips into my mouth and sucked them in. I felt Diane's body respond instantly,
and she groaned while she hungrily sucked Jen's pussy. I gradually moved up to her blood-engorged clit
and sucked it into my mouth, slurping her nectar like a starving man. Diane's legs lifted up and she dug her
ankles into my back as she tried to pull my face deeper into her pussy.
Sensing that her orgasm was coming, got up off my knees, and slid my rejuvenated cock into her naked
cunt. She shrieked, her body quaked, her pussy clenched my cock, and I was rewarded by a rush of
wetness that gushed out of her pussy. I left my cock inside her and looked at Jen's beautiful body, as her
muscular ass gyrated on Diane's hyperactive tongue, and then down at my cock, which was deep inside
Diane's young body. I was living a wet dream come true, and as the smells of pussy and sounds of raw
lust coming out of Jen's mouth, coupled with Diane's moaning, motivated me to start slowly move my cock
in and out of her. Her pussy, while not quite as tight as Jens, was hot, wet, and smooth as silk. I could
feel her inner muscles as they responded to my cock, and my pace increased as my orgasm built. I held
off as long as I could, wanting to prolong the most erotic moment of my life. But I came powerfully, and I
felt jet after jet of sperm inject deeply into her as my balls emptied.
I pulled out of her, and staggered over to the other side of the bed, where I lay down. I saw Jen take the
pillows out from under Diane's head, and move Diane's head towards the headboard. She then straddled
Diane's head, and sank her pussy onto Diane's lips as she leaned down to eat Diane's pussy in a 69. I
practically shivered with excitement as I watch these two locked hotly together, licking and sucking each
others cunts. Now Jen was sucking my load out of Diane's cunt, and I was watching Diane eat Jen's
pussy, while I was only inches away. It wasn't long before I watched them both cum, grinding their pussies
into each others face. Jen lifted herself off Diane, and Diane looked over at me, her face covered with
Jen's pussy juice. I kissed her and tasted Jen's secretions as our tongues met each other. I reached over
and cupped her beautiful breasts, and squeezed her nipples between my fingers.
Jen crawled up on my left side, and Diane was on my right. I lay back as I finished kissing Diane, and they
both draped themselves over me. I could feel both of their wet pussies on my legs, and their nipples on
my arms, and my cock somehow again started to grow. Diane grasped me tightly and whispered "Wow…".
We lay there in the afterglow, and allowed our blood pressure to return to normal. As my cock had grown
back to a full hard on, Jen reached down and started to stroke it gently. Diane, watching Jen, then
reached down to massage my balls. Jen then got up and slowly straddled me, impaling herself on my
cock. Diane then got up and straddled my face and lowered her pussy to my mouth. I stuck my tongue
into her and heard her sigh as she slowly moved herself in response to my tongue. I could feel Jen's
pussy on my cock as she moved up and down, and then looked up to see Diane leaning back, Jen leaning
forward, with her hands on Diane's breasts. They were kissing frantically, their tongues fighting each other
as they moaned. Diane's hands were clamped around my head, occasionally running her fingers through
my hair. As my eyes wandered over Diane's flawless body, I watched her abs flexing, her breasts swaying,
and hips moving to the combined rhythm of all our bodies.
I know we were in that position for a while, but it all became too much for all of us, and we all came pretty
much at the same time. My cock and balls were soaked at the same time my face got drenched, and my
cock once again delivered me an orgasm, pumping what little it had left into Jen's soaking wet snatch.
Diane lifted herself off of me, after which Jen leaned forward and kissed me deeply, and then slowly licked
Diane's juices off my face while Diane watched.
I was done. Spent. I didn't have the ability to do anything anymore, and my cock was so sore as to be almost
painful. I looked at the clock, and saw it was now 4:00am. Fortunately, I was working from home today, but
I had to be up in 4 hours. I started getting up to go to my room, but the two of them held me down, and
asked me to stay. We lay there, and Jen reached up and shut off the lights. And then I fell into a deep,
The next day was indeed a long one, and when I finally got done with the tasks of the day, I went to the pool
and did some laps, before returning home and falling asleep on the sofa. I was awakened by the sound of
Jen and Diane coming in the door, who greeted me and went off to Jen's room to continue their exam studies.
I made some dinner, and called down the hall telling them that supper was ready. In a few moments the
two of them came into the kitchen wearing long t-shirts, and nothing else. We had an uneventful dinner and they both went back to Jen's room, while I went into the living room and watched some tube while reading a
book. A few hours later they both came out to join me on the soft, one sitting on each side of me. Jen
reached for the blanket and covered us all with it so we could all snuggle together with our feet up on the
hassock. I nodded out, and woke up in time to see Diane's lovely head moving slowly up and down on my
shaft, giving me a glorious, wet blow-job, while Jen watched. It didn't take long for me to empty myself into
her mouth as she swallowed whatever had been left over from the previous night. The two of them then got
up, said they were returning to their studies, after which I went to bed and slept the night.
Jen had a major exam the next day, but Diane didn't, and she opted to stay in at the house. I spent most of the day in my office, and came upstairs for a late lunch. She came into the kitchen wearing a clingy t-shirt
(yum!), when she heard me in there, to see if there was something she could do to help, so I asked her to
cut up some veggies for a salad. I went outside, grilled up some marinated chicken, and was welcomed by
the sight of her bending over to fetch something out of the fridge and was delighted to see her still wearing
nothing underneath her t-shirt. We put dressing on the salad and began to eat, when she'd mentioned that
Jen told her I'd suggested they move in together.
"So - what did you think of the idea?" I asked. She said "it would certainly have advantages, but my older
brother is thinking of moving to town, as he wants to attend grad school. We're pretty close, and we've
discussed getting a place together". "Really?" I asked. "Having your brother living with you wouldn't cramp
your style somewhat?". "No", she said, "we're pretty open with each other". "Is he aware of your
relationship with Jen kind of open?" I asked. "Yes - he does know about that - he's the only one in my family
that does know. He doesn't care about that - he didn't like my boyfriend though" she said. "So Its convenient
that didn't work out, I gather" I concluded. Diane chucked, "well, for him anyway. But if we were going to get
a place together we'd both have a harder commute, because the school he's going to is on the opposite side of town. So either one of us, or both of us would have to suffer".
"I can see that. I was thinking more about the shorter term, since neither you or Jen is getting on well with
your roommates." I said. "Yes - besides, Jen and I are well aware of each other and our habits so it does
make some sense. I have been thinking about it" she said.
We cleaned up after lunch, and I left the kitchen heading back down to the office. Sometime just after mid
afternoon I heard Diane call down the stairs "Greg? - Can I come down and ask you something?", and I
called back "sure". I heard her coming down the stairs. She came into my office and said "Are you in the
middle of something?". And I had been taking a quick break to look through my personal email, and was
reading a few jokes sent to me by various friends. "No, not really - I was just taking a little break" I told her.
She said "Good, I was hoping maybe you would maybe do me a little favor". "Sure" I answered, "whats up?".
Diane walked over to my desk and cleared a few items and my notebook from directly in from of me, and
sat on the desk directly in front of me, pulling her t-shirt up and resting her feet on the armrests of my office
chair exposing herself to me, while leaning back onto her elbows, and looking at me expectantly. I stared
at her lovely naked pussy with its inner lips slightly distended, and at her perfectly toned legs stretching to
I moved my chair forward as she put her legs onto my shoulders and pulled me towards her. One of her
hands then guided my head towards her pussy as I opened my mouth and stuck my tongue out just as her
lips met mine, and I dug it into her. She sighed, and a little moan escaped her as I started. Her taste was
sweet, her aroma slightly pungent, and her body responded immediately to my tongue as her hand guided
me exactly where she wanted to go. Soon, her juices were flowing and I was drinking them. I pulled her
inner lips each into my mouth and sucked on them gently, as I looked up at her. Diane had pulled the
t-shirt up higher exposing her perfect torso, was now pinching one of her nipples while I manipulated
her pussy with my mouth and tongue, and I held her to me with my hands.
I then let go of her inner lips, and started to circle her clitoris with my tongue, and she then leaned all the
way onto her back and held her legs open with both hands. When she reached towards her pussy and
held the lips open to fully expose her clit I sucked it into my mouth. She was then working herself up to
a glorious orgasm, so I slid a finger into her pussy to rub her g-spot as she groaned with raw lust. Her
body started to shake, and then stiffened as I was rewarded by a rush of her liquid appreciation, that
flowed out of her onto the edge of my desk, and soaked my chin. She remained tensed and shaking, so
I stood up and dropped my sweats, and drove my now stiff member into her in one motion. Her pussy
was apparently still in the throws of orgasm, and this new invasion put her over the top. I watched with
intense satisfaction as her body convulsed and her breasts heaved.
She calmed slowly, and I just stood here allowing her body to manipulate my shaft. Diane looked up at
me, pulled me to her, offering me a deep kiss, as her tongue snaked into my mouth to salvage the
remnants of her flavors.
I pulled out of her, pulled up my sweats, smiled at her, and said "I hope that was satisfactory - but now
I've got to get back to work". She stared at me with a slightly glazed looked, smiled, and said "Jen told
me you knew how to please a girl orally… whew". She pulled herself up, stood, and turned herself to
me and hugged me, pulling me into her breasts as I sat in my chair. She then turned my head towards
her and lifting her t-shirt, presented her breasts to me. I gave each of them a quick suckle and ran my
teeth over her nipples as I grasped her ass with my right hand. I then gave her ass a little slap, and she
jumped and giggled, softly sang out a "thank you…" as she headed out of the office with her ass
sensuously swinging as she walked out and headed up the stairs.
The week progressed nicely, and the girls finished their exams in reasonable style. I got my work done,
and enjoyed a number of sessions with the two of them. It would be a beautiful thing that weekend, to
have these two hanging around when their exams were completed.
I came home from running errands later that Friday, and found the two of them half drunk on Jen's bed,
naked, in a 69, with Jen's pussy pointed towards the open door and Diane happily slurping away at it
from the bottom position. I stood in the door, watching them as my cock grew. I pulled off my sweater
and had just dropped my pants, when Diane saw me at the door. She motioned me over and used her
fingers to part the lips of Jen's cunt while she ran her tongue around her clitoris. I walked over and slid
my cock into Jen's opened pussy as she lifted her head and gasped at this unexpected pleasure. I left
my cock in there, and exulted in the combination of Jen's pussy muscles squeezing my shaft and Diane's
tongue licking my balls, and/or the union of my shaft and Jen's pussy from underneath.
I was in a form of male paradise, with two horny and gorgeous young women, both just old enough to be
daughters, demanding and performing sex acts with unbridled, hedonistic passion throughout the
remainder of the weekend.
The girls returned to school on Monday, and I had a few days alone at the house to recover before Cindy
came home. I got an unusually long e-mail from Jen, announcing that Diane's roommate had given her
notice that she was moving out at the end of the month, and since both were unhappy with their present
living situations they had decided that she should move in in the meantime.
I suggested that she clear that with her mother, since she was the one paying for Jen's room and board
at school, and this would be a new expense. But I was happy for the both of them, as it would solve
several problems, and it might be fun to mosey over for a visit from time to time.
Cindy came home, and it was wonderful to see her. Where I had been satisfied (and then some) with the
amount of sexual activity, I missed her companionship, her sense of humor, and maturity. I loved being
with the girls, but I'd knew that Cindy is the lady that I preferred. I made a special dinner for her, and had
the wine and candles on the table when she walked in the door. She was welcomed with a stiff glass of
bourbon as I took her bags, which I immediately carried off to our room as she followed me.
As she peeled off her traveling clothes, and was about to pull a set of sweats on, I came up behind her
and gave her a lingering hug, and kissed her beautifully exposed neck. I was satisfied by the rising of
the goosebumps all over her body and the sight of her nipples stiffening on the tops of her breasts. She
turned and we kissed deeply. I was going to leave her alone then, as I wanted to give her the option of
merely accepting my deep affections and have dinner, or otherwise, when she pulled me to her and
whispered "and where do you think you're going?".
We fell into bed, and alternated between glorious raw sex and love-making. We then got up, and in
robes only we walked hand in hand to the dining area and had a relaxing dinner. After cleaning up
and putting away what we had to, we went back to bed and just enjoyed each others presence.
Neither she nor I did any work the next day, and just spent it together making up for lost time.
We went to Bermuda the following week, enjoying our stay just outside of Hamilton in a boutique
hotel with stunning gardens. The weather was unseasonably warm, and it was wonderful to see
Cindy laying out in the sun in her bikini. The subject of Jen of course came up, and Cindy asked me
if she behaved herself. Given my point of view, I gave her a qualified "Yes", and told her about Diane
coming to stay over, and her roommate problems, etc. Cindy was relieved that Diane came over to
stay, probably assuming that that would've curbed any of Jen's efforts to ensnare me. I told Cindy
about Diane's roommate giving her notice, Jen's wanting to move in with her, and a head's up that
that conversation was on the horizon. Cindy thought about it, and mentioned that since there wasn't
that much time left in the semester that might not be a bad idea. She was more interested in Jen being
productive at school, and since she did get good grades and obviously worked hard to get them,
she'd consider that carefully, and would likely approve.
So it seemed that there might be some interesting times coming for Jen and Diane...