Events during first serious relationship, post-divorce
It Started At The Pool - Part 4
I you haven't read the first three 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 4 finds Cindy and Greg are in Bermuda at a boutique hotel just outside of Hamilton. Jen and Diane are
both having roommate problems, and since Diane's roommate decided to give her notice, the two of them
want to move in together, but are awaiting Cindy's ok.
Greg is interested in this development, as it might make things easier around the house, and it might also
be safer or less risky to drop over to "visit" the girls on occasion.
Considering the time of year, Bermuda was still a pretty quiet place, as the tourist season had yet to
begin. Subsequently, Cindy and I had the place to ourselves for the first few days. Then another
younger couple, Tom and Sandy arrived. Cindy and I were hanging around the pool area and patio,
but as the pool wasn't terribly great for lap swimming, one could still get exercise. Cindy was
lying in the sun on one of the chaises in her bikini, catching some rays. She looked like the image of
her daughter lying there, and still has that capacity to make men (and me) stare despite being north
of 40 years.
We met Tom and Sandy as they came to the pool to relax, and they were clearly a much younger
couple. Each of them was probably about 30 or so, and Sandy, who wore a lovely little (and I mean
little!) bikini that was comprised of little more than maybe 5 square inches of cloth (tops), and a few
strings to hold it all together. I'd guess she was maybe a size 6, and her breasts were easily C-cups.
Her muscles were toned, so it was obvious that she lifted weights or did some other kind of exercise
on a regular basis. Her hair was short and dark brown, and as I learned later, had green eyes.
Tom was a bit shorter than me, but also in reasonable shape. He wore a standard boxer-style
bathing suit, had sandy-brown hair and a medium build.
I took notice of Sandy as soon as she came out of the side entrance to the hotel wearing robe, and
when she shook it off I was taken back by what a great figure she had. She pulled one of the other
chaises over near where Cindy was sunning herself (as she was fully exposed to the sun, the other
chaises were in a shaded area) and reclined back on her chaise.
Tom followed her out, dragged another chaise over next to Sandy's, dropped off a few things, and
then dove into the pool. We eventually introduced ourselves, and started to chat. Apparently, they
had both decided to take a few days off, and had dropped their only child (a son) at Tom's parents
house to spend some time alone relaxing. We took note that the women had started chatting, and
Tom asked me how old Cindy was. When I told him she was over 40, he was visibly stunned, and
told me I was a lucky man. I grinned and agreed with him, saying from the looks of it he was also
We chatted about current events, sports, our careers, and other stuff when he piped up with "how
liberal is Cindy?". No one had asked me that question before, so I asked him "can you define
liberal?". He smiled, and said he hoped I wouldn't be offended, but said that his wife Sandy was
also rather fond of women. When they arrived, Sandy looked outside their window down at the pool
after they checked in, saw Cindy sunbathing, and insisted on heading for the pool immediately. I
told him that that was a topic I had never explored with her, as she was my girlfriend, and though
we lived together for some months that topic never came up. As far as I was concerned, it didn't
bother me, but I couldn't speak for Cindy.
Tom laughed, said that Sandy would take it slow, would very likely find out, adding that she
usually preferred younger women, but that Cindy just blew her away when she first saw her. I
smirked at that comment, saying that I'd had the same reaction when I met her myself.
It wasn't long before one of the hotel staff came out and walked over to the ladies, who were chatting
up a storm. Cindy called over, and asked if I'd like a cocktail. I looked at Tom, he said "sure", and
I said "we're both up for a drink if you're ordering". She waved and the guy from the hotel vanished
inside, eventually returning with some drinks. I hadn't gotten the full workout, but figured what the
hell, and called out to the women and asked them to bring our drinks over. Cindy and Sandy both
got up and brought our drinks over, and sat with their legs dangling in the pool. When Cindy put
hers down I reached up and pulled her into the pool with me as she shrieked with surprise. Tom
quickly followed suit, and Sandy also got dragged into the water.
Cindy quickly jumped up on my back, so I was giving her a piggy-back ride around the pool. Tom
and Sandy were soon doing the same thing. The horsing around quickly deteriorated into Cindy
and Sandy trying to dislodge each other from my or Tom's backs, each riding their man as if they
were jousting. They were shrieking and laughing like school girls, when Sandy was successfully
dislodged from Tom's back by Cindy. When she fell off, her top became unfastened, and mostly
fell off. Cindy then let herself off of me, and swam over to sit in front of Sandy while she put her
top back on. I heard Sandy say "here - get closer - I don't want him to see me", and as Cindy
backed herself to her Sandy reached for her shoulders and pulled Cindy in front of her. So close
I was sure, that her breasts were pressed into Cindy's back.
Tom and I were laughing (me pretending I had no idea of Sandy's attraction to women), but I was
watching Cindy carefully. Her eyes got really big, and she was clearly surprised, but pretended that
it was all in good fun, as Sandy took longer than I would've expected to put her top back on (women
who are in a hurry do that very quickly, I've noticed). After she got her top back on, I saw Sandy
whispered something into Cindy's ear, and then released her. Cindy then swam back over to me,
pulled me close to her, and then suggested we get out to enjoy our drinks.
We got out of the pool, picked up our drinks, put them on a side table, and I went and pulled
one of the comfy easy chairs over, next to Cindy's chaise. Tom and Sandy also climbed out as
we sat down, clinked our glasses, and took a good pull off our drinks. Cindy had ordered
us mai-tais, which were pretty lethal - whoever poured them was heavy handed on the rum
bottle. We hung around the pool for a while chatting with Tom and Sandy - they were both from
New York and had gotten married in Bermuda at this hotel several years prior. Another few
rounds of drinks went by, and eventually the sun got a bit hot, so I suggested to Cindy that we
head inside for a nap prior to going out for dinner. Cindy excused us, saying that we were heading
for our room for a nap, when Sandy suggested that we have dinner together.
There wasn't much going on on the Island since it was still too early for tourist season to begin, so
Cindy took down their room number and said we'd get back to them a little later, and otherwise we'd
see them tomorrow. They said that was fine and back to our room we went.
As soon as we got into our room, Cindy let her robe drop, took off her bikini, and announced that
it was time to wash the chlorine off. So I dropped my swimsuit and towel and we stepped into the
oversized shower in the bathroom. We soaped each other over and kissed deeply in the shower,
enjoying the feeling of the slipperiness of the lather as we held our bodies together. I became
aroused while I was soaping down Cindy's back, and I pressed my cock into ass as I caressed her
breasts. She moaned happily and quietly suggested we get out of the shower. We rinsed off and
dried each other carefully. Cindy took out the hairdryer, and turned it on while I moved into the
bedroom and lay out on the bed.
She finished her hair quickly (her shorter hair made that a much faster chore), opened the door,
and sensuously walked over to the bed where I was laying. I watched her as she came to me,
smiling. I moved over to make room for her. She climbed onto the bed and lay on her side next
to me, pulling me close, and kissing me deeply. She turned over and asked me to hold her, which
I did happily, running my hands up and down her body, as she sighed.
I asker her if anything was wrong, and she said "I'm not sure". "How so?" I asked. "Remember when
we were in the pool, I knocked Sandy off Tom, and her top fell off?" she asked. "Sure do" I said,
"that was hilarious". "Well, remember that I went in front of Sandy to hide her breasts from you while
she put her top back on?" she asked. "Yes - I saw her pull you back" I said.
"She sure did, in fact she pulled me so far back that I could feel her pressing breasts in my back" she
said. "Oh. And?" I sad. "She said she hoped it wasn't too forward, and didn't want to offend me, but
that she really found me very attractive" said Cindy. "Really. And how did you feel about that?" I
asked her. "I'm really not sure" she said, "she is a lovely woman, so in a sense I suppose I should be
flattered. But I love you" she said. "And I love you" I said. "Is there anything else that happened
there that I should be aware of?" I asked, and I slid my hand down and pulled her over so she was
lying on her back. I then ran my fingers between her legs, and noted that Cindy was really wet.
"Hmmm…" I whispered into her ear. "Hmmm what?" she asked.
"You'll have to pardon my observation, but you're awfully wet. Are you sure you're not really sure?"
I asked softly. "I've never been with a woman and never even considered it" she said, "and I just
don't know about that. Still, she is a lovely woman and I found it flattering", said Cindy. "And
arousing" I said. I started to kiss her shoulders, and slowly up her neck. Then I moved over her and
gave her a deep kiss, as she put her arms around me and clung to me. I ran my tongue down her
neck to her breasts, took each one into my mouth, working her nipples until they stood up, and kissed
her down to her abdomen while I ran my hands over her body. I soon moved between her legs, and
kissed the insides of her thighs, eventually centering on her pussy. She was soaking wet, her inner
lips already parted, open, and inviting. I reached to her with my tongue and licked her from the bottom
to the top of her slit, finishing at the top of my initial assault on her pussy by sucking her clit gently into
my mouth as her hips thrust up to meet me. Her back arched in pleasure, and she moaned lustfully.
I stayed centered on her clitoris and kept sucking it into my mouth, drinking her juices as her hips
gyrated slowly and her fingers ran through my hair.
I moved down a bit and then dug my tongue into her opening, pushing it in and out to fuck her. Now
her hips were moving with me as much as she could, when I moved back up to her clit, found her magic
button, and circled it with my tongue. Her body instantly tensed, she pulled me into her pussy as
I sucked her clitoris and she rewarded me with a rush of wetness, grinding her pussy into me while I
sucked her. I rejoiced as I looked up at her tight body, frozen, with her abs beautifully defined, her
eyes clamped shut, and mouth open, as she held me in place. When I moved my tongue she pushed me
away and covered herself, gasping out "too sensitive, too sensitive". I looked down, and there was a
considerable wet spot on the linens.
I pulled myself up over her, and my now rock-hard cock found her opening. I slid into her in one
motion, and lowered myself to her giving her a deep kiss as she tried to drink all the fluids out of my
mouth. "See how good you taste?" I whispered, as I started to move in and out of her. Her body
began to respond immediately, and soon I was up with my arms fully extended, watching her push
herself up to meet my thrusts, her breasts heaving, eyes shut, and smiling. I was really turned on
watching her, and I felt my orgasm building. Her body began to tense as her inner pussy muscles
started really working over my shaft. I looked down to see my cock sliding in and out of her, felt
my balls slapping against her pussy, when it all became too much and I felt my cock almost vibrate
as several ropes of sperm injected into her womb, the impact of which made her come. I watched
her body thrash as her inner muscles almost squeezed me out of her. I pushed back, feeling her
pussy grasping my cock. Eventually I collapsed on top of her, leaving my still hard cock inside.
"Ya know" I said, "I don't blame Sandy for propositioning you."
Cindy smiled and said "oh yeah? Why?". "Because I find you deeply attractive mentally and physically,
and I love sharing a bed with you, thats why" I said. "You were right", she said, "her propositioning me
did kind of arouse me". "So, what are you going to do?" I asked. "I wouldn't even know where to start"
said Cindy, "and why are you encouraging this?". "I'm not encouraging anything. Aren't you the one
who determines who you're going to have a relationship with?" I asked. Cindy said "but I told you
I love you". "And I love you", I said, "don't forget that, but is your arousal, caused by her propositioning
of you, mean that you're automatically going to fall in love with her and leave me?". "Certainly not"
said Cindy. "So, if you're in love with me, but she arouses you, and you're still aroused by me, then…"
I let that thought just hang out there.
Cindy looked the card on the nightstand, picked it up, and punched the number into the phone. I heard
Sandy pick up the phone "Hello?" she said. "Hi Sandy, this is Cindy. We'd love to have dinner with
you guys tonight if you're still up for it". "Sounds great, shall we meet a 6:45 in the lobby?". "Sure,
that sounds great. See you then", said Cindy.
She looked at me, lay beck down next to me, and draped herself over me sideways. "We're going to
take this very slow, and see if it goes anywhere. I'm not sure I"m ready for this: I could've read the whole
thing wrong; she might back off; maybe she didn't mean anything at all; and maybe I'm not ready. Don't
be shocked if nothing happens" she said. "I have no expectation outside of you and I having a wonderful
dinner, and a wonderful time together. If the slightest hint of anything goes south, we're excusing
ourselves and going our own way. If you're not comfortable, if you're not having fun, anything. Period",
I said. "Thanks for being so understanding" she said, clinging to me, and kissing me deeply.
We dressed for dinner, and met Tom and Sandy in the lobby. Tom had made a reservation at one of
the nearby restaurants. I'd been there before on a previous trip, and it was excellent then. So we
jumped onto our motorcycles and off we went into town. Once we got there, the women brushed their
hair and in we went. This restaurant specialized in seafood (we were in Bermuda, after all) and dinner
was excellent. We drank a few bottles of wine with dinner, and had a nice buzz going. Over dessert,
Tom mentioned that he'd visited a liquor store and bought a few more bottles of wine, and suggested
maybe we should head back to the hotel and have one as a nightcap. The ladies, who had been sitting
next to each other and giggling over dinner agreed, so off we went after paying the bill.
We got to the hotel, and the place was almost deserted. The lights were on in the entryway and halls,
but otherwise empty and we had the place to ourselves. It was unseasonably warm, so Tom ran up
to their room to get a corkscrew, and the rest of us went out to the pool area. We sat around the pool
area where our chairs and chaises were, and I'd noticed a raised platform earlier that had either a
wading pool or hot tub. I stuck my hand in the water, found it was a hot tub, surrounded by lovely plants
and freshly blooming flowers. I walked the 5 yards back to the others, as Tom returned with 4 glasses,
a bottle, and a corkscrew, and mentioned there was a hot tub just behind this bank of shrubs.
Tom opened and poured the wine, so we sat around sipping it, enjoyed each others company
and the evening. The lights were on in the pools, leaving just enough ambient light to see our way
around. After a few glasses of wine each, we were all getting silly, and Tom ran up to get another
bottle of wine. Sandy got up and walked over to the hot tub and called Cindy over to have a look.
Cindy got up and went over to see, and I could hear her say how pretty it was. The moon had been
rising, and was three quarters full, so it was throwing additional light, much brighter that it usually
is at home. Tom came back with another bottle, opened it up, walked around refreshing
everyone's glasses, and mentioned how nice the tub looked. "Maybe we should get our bathing
suits and partake of it" I suggested.
Sandy snorted, and announced "we're all adults here, I'm going in now - we're the only ones here, and
I don't care. With that, she unbuttoned her dress, and shrugged it off her shoulders. It dropped off
of her, leaving only a tiny black thong. Her breasts were lovely, hanging down slightly, with her nipples
sitting on top, kind of looking up at you. She reached down, slid off her thong, and when she stood up
and stepped towards the hot tub and lifted her leg to step over the edge. I could see she was clean
shaven, with the hood of her clit just sticking out of the top of her pussy. She settled into the hot tub
with an "ahhh…" and said "well? am I the only one? Tom, be a good guy and hand my my glass".
Tom hustled over to pick up her glass, which was just out of her reach, looked at us, and shrugged.
Cindy and I shrugged and started pealing off our clothes. Then Tom and Cindy stepped into the tub as
well, Cindy sitting next to Sandy, as I grabbed the bottle of wine and then settled in next to Cindy.
We all had a toast, announcing that this was all "very civilized" and downed our glasses. I refilled
them and our conversations continued into the evening, getting more ribald as it progressed. After
some period of time, Sandy, who had been laughing and whispering stuff into Cindy's ear, had
been turning to her while doing so (thereby rubbing her breast on Cindy's arm), announced that she
was getting too hot. So she stood up turning towards Cindy, making quite certain that Cindy (and I)
got a good look at her pussy before she settled down on the edge of the tub. Cindy then announced
that she, too, was too hot, but she was going to jump in the pool. So she got up, jumped out of the
hot tub, and sprinted for the pool. I heard a big splash as she jumped in. Sandy got up and ran over
to the pool, and I heard her jump in as well, and after a few shrieks I stood up to see the the two of
them laughing next to each other. Then the laughing stopped, and Sandy moved closer to Cindy.
Cindy didn't move away, and I saw Sandy's hand come up and brush the side of Cindy's face and
run her fingers through Cindy's wet hair as she inched forward.
I saw her stare directly into Cindy's eyes and leaned in for a tentative kiss. Cindy didn't move away,
she just looked at Sandy, who went in for a second kiss, and allowed that one to linger. Now Sandy
have moved so that Cindy had to be feeling her body heat even in the pool. When she didn't
pull back, I saw Sandy's arms snake around Cindy as she pulled her in for a much deeper kiss.
Her tongue snaked out of her mouth, and when I thought Cindy was going to back away I saw her
mouth open, allowing Sandy's tongue in. I looked over at Tom, and mentioned that the ladies were
becoming friendly. He whispered that while he got to watch, Sandy didn't let him participate very
We both stepped over to the pool, and I sat down with my glass of wine in the chair I'd moved over
there earlier in the day to watch. The two of them continued kissing while up to their necks in the
water. I saw Cindy's head move over to expose her neck to Sandy, and I saw her body stiffen before
it relaxed, making Sandy smile. I gathered by that movement, that Sandy's fingers had found their
way into Cindy's pussy. They moved over to the shallower section of the pool, which was nearer to
where I was sitting, when I heard a noise next to me. Tom pulled one of the chaises over so he could
watch, and was settling into it with a glass of wine.
Then Cindy half got up or was half lifted onto the side of the pool, and she leaned back onto her
elbows. I saw Sandy as she moved closer to her, and while looking her directly in the eyes gently
pushed Cindy's legs apart. Sandy stood and moved between Cindy's legs, puller her up, and
kissed her deeply, their tongues aggressively searching each others mouths. Sandy then started
to kiss her way down Cindy's neck, to her breasts, taking her nipples into her mouth. I heard
Cindy gasp, as Sandy tweaked her nipples between her thumb and forefingers. Then Sandy moved
down as she pushed Cindy back, pulling her legs up, and started to kiss the insides of her thighs.
Cindy was shaking and I could hear her breathing becoming irregular. She mewled when Sandy's
tongue found its way between her legs, and I saw her abs suddenly flex as her body started to
respond. Soon we could both hear Sandy slurping at Cindy's cunt, and Cindy was moaning
quietly, but with obvious lust. Cindy's legs lifted up, and planted her heels in Sandys back, drawing
her closer, as her right hand pulled Sandy's head into her pussy.
Then I saw the telltale sign of Cindy's body stiffening, so I knew she was about to come. My cock
was as hard as steel, and I hadn't even realized that I'd begun stroking it while watching this super
erotic scene taking place. Shortly thereafter, Cindy's body convulsed as she came and cried out.
She slowly released Sandy, who moved forward, slowly getting out of the shallow end of the pool
while straddling Cindy, and bent down to kiss her. I saw Cindy returning her kisses, and knew she
was tasting herself. Sandy looked at her questioningly, and Cindy simply pushed Sandy around
the other way, slid under her as Sandy lifted her leg, and pulled her down to her mouth. I saw
Cindy's tongue stick out to meet Sandy's pussy, and dig into it. Sandy shuddered, lowered her
head down in between Cindy's legs, and started to pleasure her orally once again.
The two of them were locked together, and Tom and I were both stroking ourselves while watching
the women in our lives work each other over. It didn't take long before the two the them came
together, moaning as they drank each other juices. They both got up, looked over at me and Tom,
and walked over to us. Cindy came over and kissed me frantically, and I tasted Sandy's juices when
she stuck her tongue in my mouth. She then knelt down and took my cock deeply into her mouth,
running her tongue all around the head and shaft. Cindy then pulled me off the chair, and reached
over and pulled Sandy off Tom's cock, and whispered in her ear. Sandy smiled, and got on all fours
facing Cindy. Cindy got on all fours facing her, and they started to fresh kiss each other frantically.
I knelt behind Cindy, and slid my super hard shaft into her from behind, as I watched Tom to the same
I was already close by the time Cindy and Sandy were done with their 69, and now my orgasm
came boiling up from within me and pumped deep into Cindy's cunt, as her pussy milked my
cock. Tom came shortly afterwards, if not at the same time, in Sandy's pussy. Sandy then
pulled a cushion off one of the chaises, and settled down onto it, motioning Cindy over. I saw
Cindy crawl over to Sandy from the opposite direction, first kissing her face. She then moved
down Sandy's body so that they were both sucking on each others breasts. They both worked
their lips, tongues, and hands down each others body until they returned to another 69 with
Cindy on top. They ate each other out, sucking the cum out of each others pussy, until they
both came again, heaving and moaning into each others soaking wet snatch.
They both stayed there until they recovered, and then slowly untangled themselves. Cindy
wavered on her feet, and she stepped gingerly over to me and sat on my lap, picked up her
glass of wine, and drank deeply. "I've had enough for tonight" she declared. So I got up and went
over the the hot tub to collect our clothes, and went back to my chair where Cindy was now
passed out. Tom looked over and chuckled, and asked if I needed any help. "Thanks, I think
I'll be fine - she's pretty light" I said. Had a great time tonight. We'll probably see you both
tomorrow" I said.
I put my pants and shirt back on (it was easier to wear than to carry them) bundled the remaining
clothes up, and put them on the edge of the chair. I then picked up Cindy, who was more or less
passed out, hefted her over my shoulder in a fireman's carry, and head back to our room. Once we
got back, I put Cindy gently on the bed, and went to the bathroom. When I came back, she was
sitting up, but looked somewhat worse for the wear. Cindy looked at me with bleary eyes, when
all of a sudden they got real big and she ran into the bathroom to drive the proverbial porcelain
bus. She then spent the next half hour in the bathroom, dealing with the consequences of drinking
too much, and finally came back out looking rather embarrassed.
"Ohhh… I drank far too much. Why didn't you stop me?" she asked. "Um, I've never seen you
drink that much and I assumed you knew what you were doing" I said. "And what have I done?
what you must think of me" she moaned. "I think my lady drank too much, and that she'll learn
the error of her ways. But now she should drink a few large glasses of water and go to sleep"
I told her. "Why water?" she asked. "Because alcohol is a diarrhetic, and if you don't, you'll have
a hangover you'll never forget" I said. I went and got her a big glass of water and handed it to
her, and she reluctantly drank it down, plopped down on the bed, and immediately passed out.
She was obviously done, so I put her naked body under the covers, left another big glass
of water on the nightstand next to her, in addition to a few Midols (great pain killers), shut off
the lights and went to sleep.
The next morning, I woke up, and Cindy was still out cold (but breathing normally). The other glass
of water and Midols were gone, so I assumed she'd at least be in fair shape when she finally
awoke. Since it was close to 9:00am, I got up, left her a note telling her I'd gone downstairs for
breakfast, and shut the door quietly.
I ran into Tom, who was just starting breakfast, and he waved me over. I asked him where Sandy
was, and he said still in bed. I gave him the same answer for Cindy. I ordered breakfast, and upon
finding out that the kitchen would soon be closed I ordered some for Cindy, too, but asked for it to
come when I was just finishing. We chatted through breakfast, and I had several cups of coffee and
a big glass of OJ, and I began to feel pretty good. Cindy's breakfast showed up, so I told Tom we'd
maybe seem them later, picked up Cindy's breakfast and the pitcher of coffee and headed back up
to our room.
Cindy had just wakened when I came in, and looked lovely, despite being clearly hung over. "Here
sweetie, I brought you some breakfast - I hope I chose well for you this morning because the
kitchen is now officially closed". She was still naked from the previous night. She got up, went to
the mirror, shuddered, said "I'll be a few minutes", and went into the bathroom. About 5 minutes
later she came back out looking somewhat better, wearing one of the hotel terrycloth robes, and
sat down at the table. She just quietly ate breakfast, and drank coffee, and I read my book on the
balcony. After she was done, she put the tray outside the door, and came over to the balcony and
beckoned me inside.
She shut the balcony door, buried her head in my shoulder and starting crying hysterically, clinging
to me. "Whoa" I said, "whats all the waterworks for?". "I am so ashamed. Oh my God I am so
ashamed. What you must think of me. How will I ever live this down?" she bawled. "Stop it…
C'mon, stop it. Everything's fine. What's wrong?" I said, trying to console her. "I wouldn't blame
you if you left me" she sobbed "I've been so irresponsible… I am so embarrassed. I'm so..".
I put my finger on her lips, and she looked up at me, and her eyes were red, and she had tears
running out of her eyes. My heart went out to her - obviously she was deeply distressed. So I
pushed her back onto the bed and cradled her head in my arms, and then moved her head into
my lap. She lay there facing into me, her body shaking. "How's your head feel?" I asked her softly.
"Its actually not that bad. That extra glass of water and pills you left me really helped. What were
they?" she asked. "MIdols - they were the only pain relievers in our bags that I could find", I
answered. "Hmmm. When I woke up and felt like I'd been hit by a truck, I just saw them there,
and downed them with the glass of water you left me. They really helped. Now I'm just tired" she
said. "Then why don't you take a nap, and I'll go and read by the pool in the meantime?" I suggested.
I got up and looked out at the pool, and saw Tom and Sandy already out catching rays. "We could
just go and hang out by the pool, as an alternative" I suggested. "But what if we see Sandy and Tom?"
she said, and started crying again. "What if we do?" I answered. "You're not getting it - how can I
face them today, or any other day?" she said. I sighed. "If they aren't ashamed, why should you be?"
I asked. That got me no answer, so I offered "Tell you what. How about if we go into town and wander
around. Hamilton is a nice town, and there are a lot of interesting shops and restaurants there. Lets
go there, decompress, and have lunch. We can ride out to the beach later and maybe go for a swim
or something?". Cindy bought that, and decided to take a shower first. So she got up, dropped her
robe, and headed into the bathroom. I took off my clothes and followed her into the shower, after seeing
the outline of her magnificent figure in the frosted glass. As I got in, her figure aroused me, and I pulled
her to me.
Cindy stood there as I lathered her from head to foot and pressed myself to her. She turned around and
put her arms around my neck and kissed me deeply. She cleansed me all over, got down on her
knees, took me into her mouth, and made oral love to me. I just stood there and enjoyed it, and
whenever I tried to pull out of her to head for the bedroom she held me in place, until my orgasm came
and I emptied my balls into her mouth. She stood, proceeded to rinse us both off, and shut off the
water. We dried each other off, moseyed back to the bedroom, where she lay herself out on the
bed, and I lay down next to her. She looked at me with a little smile, and I leaned down to kiss her.
Cindy put her arms around me, kissed me back, pulled me to her. My cock was becoming aroused
again, and she reached down to stroke me. She then pushed me up, slid underneath me, and guided
my now hard cock to her opening as she wrapped her legs around me, pulling me into her. "Make
love to me…" she whispered.
She was looking at me with almost pleading eyes (apparently still upset from the previous night). I
smiled at her as I enjoyed the union of our bodies, feeling her pussy stroking my shaft with her velvety
and wet walls. I started to slowly fuck her, and looked down to see my now wet shaft sliding in and out of
her. Our pace gradually started to pick up, but I wanted this to last so I lowered myself to her onto my
elbows. I took her face in my hands and kissed her deeply to ensure she got the message, and again
started to slowly move in and out of her as I grasped her ass to help her move with me. We were
moving together in harmony, as she arched her back in pleasure and clung to me. I picked myself
up, moving down her body quickly so I could pleasure her pussy with my mouth. As I sucked her clitoris
into me her body instantly stiffed and she cried out softly, starting to convulse. I drank the juices
that were flowing out of her, and when she started to shudder I picked myself up and slid my cock
into her. Her body froze as her legs squeezed me, and I watched her tremble as her orgasm
subsided. As soon as she loosened her grip, I started to piston in and out of her, feeling the need
to seed approaching. Cindy looked up at me, smiling, thrusting her hips up to meet me, clenching my
cock with her inner muscles. It all became too mug, and I finally came, injecting hot sperm into her.
I let myself down atop her, and she held me as if it was the last time we would ever be in each others
arms. She then softly asked "Are we ok?". "Of course we're ok" I said, "let me ask you this: did your
having sex with Sandy last night diminish your feelings for me?". And Cindy answered "Absolutely
not". "So, does that realization help you at all?" I asked her. "I'm having a hard time with this, but I see
your point. I'm just trying to internalize it" she said. "C'mon woman - lets get dressed and head into
town, and see some more of the island" I said.
So we got dressed, and walked over to our little motorcycle, waving at Tom and Sandy who were still
at the pool, and took off. We had a great time, as Bermuda has some lovely towns, and the people are
really friendly. We met a couple of Bermudians at a local restaurant who invited us to a party at their
place, so we exchanged numbers and email addresses before heading back to our hotel.
Cindy wanted to lie out in the sun, and I felt like taking nap (as it was early-mid afternoon), so she put
her bikini on and headed for the pool while I lay out of the chaise on our balcony and read.
Sandy waved at Cindy when she showed up at the pool, as she was still sunbathing. Tom had
apparently run into a business acquaintance and had just taken off for the afternoon to play 18 holes
of golf. They lay about and chatted when a breeze came up and made the poolside area cool way
down, so they packed up their stuff to head back in. Once inside, they ran into one of the hotel maids
who had just been outside as well, and noted the sudden drop in temperature. She suggested that
they try the new roof deck, and asked the ladies if they wanted to see it. They looked at each other and
said "Sure" and up the stairs they went.
When they got to the roof level and the maid opened the door there was a lovely walkway, lined with
flowers. And when they got around the corner, there was a walled-in area with two large, upholstered
chaises that were protected from the wind, so it was much warmer. And, if they wanted to look at the
view all they had to do was step out of the walled area, where a deck had been built, for a lovely view
of the harbor. The maid told them that the deck and sunbathing area was theirs to use, and since no
other guests were due, it would be most private.
So Sandy looked at Cindy, and said "looks good to me". Cindy apparently looked reluctant, so Sandy
suggested they just sit and chat. They both sat down, and Sandy asked if Cindy was uncomfortable for
some reason, to which Cindy nodded and said "yes". "Did it have anything to do with the other night?"
Sandy asked. "Yes" said Cindy.
"So whats the problem?"
"Well, I hadn't done anything like that before, and I'm feeling a lot of regret".
"Why, did Greg not approve?"
"No - Greg seems ok - I'm just not comfortable myself. And, I had a terrible hangover".
"Well, that isn't the fault of having sex with me, is it?"
"No, but that might've been what caused me to… let go".
Sandy smiled at her. "You seemed to really enjoy it. Your mind might've been saying no, but your
body certainly said 'yes'. You did enjoy it - didn't you?".
Cindy sighed. "Yes, I suppose I did, but what would my daughter think?"
"Do you tell your daughter the details about every time you have sex? Does she ask you or tell you
about your or her activities?".
"No. Of course not."
"So whats the problem? You don't tell people what they don't have to know. I never do, and wouldn't
dream of it. That only causes more problems than its worth. Anyway, you're starting to get a little pink, have
you put any sunblock on?"
"Whoops, no. Could you hand me my little bag? - its right next to you".
Sandy handed Cindy her bag, and she fished out her sunblock, and starting applying it liberally all over
herself. Then she got stuck dealing with the middle of her back, so Sandy offered to put it on for her.
Cindy seemed reluctant, so Sandy said "I promise not to bite - come on, lets be adults here." Cindy
relented and Sandy squirted some sunblock onto her hands, and started to rub it into Cindy's back.
Cindy was really tense, and that certainly drew Sandy's attention, so she suggested that Cindy lie face
down on the chaise. Cindy, after some cajoling, finally relented and lay down. Sandy started to work
her over, starting at the base of her neck (which she really likes), over her shoulders, and methodically
down the rest of her body. Sandy became aroused by Cindy's toned body - she was indeed gifted with
having a youthful figure that a lot of far younger women envied. She could feel herself getting wet, and
her nipples hardening. But she knew Cindy had already put sunblock on the rest of her body, so she
asked Cindy if she would mind putting some sunblock on her back.
Cindy got up and turned herself over to sit up just behind Sandy. Sandy handed her the bottle and
Cindy asked "where do you want it?". Sandy said "just do my back please", and as Cindy finished her
lower back and moved up a bit, Sandy reached around and unsnapped the bikini top and let it hang
on her shoulders so as to not alarm Cindy. Cindy hesitated, but then continued to apply sunblock. She
found herself enjoying the feeling of Sandy's skin underneath her hands. Sandy was now quite wet, and
asked Cindy if she minded if she sunbathed topless. Cindy, who was now becoming aroused but was
trying not to show it said with a reluctant tone of voice "Ok…".
Sandy let her top drop off, and turned around to look at Cindy. Cindy's eyes went to Sandy's firm
breasts, who's nipples were clearly swollen and hard. Sandy took a little squirt of sunblock and started
to rub it thoroughly onto her breasts, obviously lingering on them as she watched Cindy's reaction.
Cindy's gaze was on Sandy's breasts, when Sandy said "well, are you going to join me?". Cindy sighed,
feeling the wetness below starting to grow, and gave in. She unsnapped her bikini top and applied some
sunblock to her breasts. Cindy found it oddly arousing that she would be massaging her breasts in
front of another woman, yet here she was.
So they both lay back on the chaise and just chatted about life and other topics as they arose, eventually
forgetting that they were both naked except their bikini bottoms. At one point they were laughing at
some pun, when the bottle of sunblock fell off the chaise and they reached for it, knocking it further out
of reach. They both reached for it again, laughing, when their bodies collided and they both froze.
Cindy's mouth was wide open, and Sandy leaned down to kiss her full on the mouth. Cindy looked
stunned, but remained where she was. Sandy looked at her, leaned in again, kissed her slowly, and
snaked her tongue into Cindy's mouth. Cindy, now aroused even more, and noticing her wetness, found
herself kissing Sandy back. They both rolled onto their sides, facing hear other, their tongues dueling.
Sandy reached up, and started rolling Cindy's nipples between her fingers. Cindy was seriously
aroused, and still reluctant, but Sandy's fingers working on her nipples transmitted an electrifying
sensation straight down south, centering on the cleft between her legs.
She reached over and pulled Sandy closer, and then traced her hand down Sandy's body. Sandy reached
down and grasped Cindy's ass. Cindy rolled onto her back, pulling Sandy on top, and Sandy ground her
pussy into Cindy's. The two of them kissed frantically, and Sandy started working her way down Cindy's
body. She got to the bottom of her torso, moved her fingers under the elastic at the top of Cindy's bikini
bottom, and pulled it down so that she could kiss and tongue below her bikini line. Sandy took note of
Cindy's landing strip, and concentrated on following it down to the target of her desire. With her other hand,
she moved Cindy's bikini seat to the side, and stroked her tongue from the bottom to the top of her pussy.
Cindy's body tensed when she felt Sandy's tongue on her pussy. She felt her body shudder as her tongue
circled her clitoris. Sandy reached up with both hands, worked her fingers under each side of the bikini
and tugged. Cindy lifted her hips, and Sandy pulled them down, off, and put them aside. Sandy then
spread Cindy's thighs and pushed them up, digging her tongue into Cindy's wet pussy. Cindy's body
responded, and her legs wrapped around Sandy's back. Sandy slowly sucked each of Cindy's inner pussy
lips into her mouth, and gently sucked them in, drinking the juices that now flowed freely out, intermittently
digging her tongue deeply into her opening, and tongue fucking her as her body writhed and back arched
in pleasure. Sandy looked up, and watched as Cindy's head turned back and forth as she moaned with
lust and pleasure. Sandy could now feel her cunt obviously very wet inside her own bikini bottom, so she
wormed her way out of it while she fed on Cindy's pussy.
Cindy's body tensed, and her hands grasped Sandy's head while her body convulsed, and she came.
Sandy eagerly drank her juices in, and when Cindy released her, she stood up over Cindy looking down
at her. Cindy looked up, and Sandy reached down to help her up, and Cindy gave her her hands. Sandy
then pulled her up, and putting her hands on either side of Cindy's head, pulled it to her, guiding her lips
towards her very wet pussy. Cindy stuck her tongue out, and pushed Sandy's legs apart as she got onto
the floor, on her knees. Sandy's hands ran through her hair as she felt Cindy's tongue digging into her.
Soon her legs and hips were pumping to the rhythm of Cindy's tongue.
Sandy then pulled Cindy up, pushed her down onto the chaise, set the backrest level, climbed over
her straddling her face, settled her pussy down onto Cindy's lips, and leaned forward to eat her snatch.
The two of them were now together as one, drinking each other, and moaning with pleasure when I
Given Cindy's and my discussion earlier in the day, I was somewhat taken back, but was certainly glad that
the maid had told me about the deck on the roof. I stood there watching them, when Sandy noticed me
and gave me the "come here" signal with her fingers. I dropped my swimsuit as I walked over, knelt down
in front of Sandy and slid my cock into Cindy's pussy. I heard a satisfying gasp come out of Cindy as I
bottomed out inside her womb. As I pulled out Sandy licked the shaft of my cock and Cindy's clit. I moved
in and out of her enjoying seeing Cindy's hands on Sandy's ass, holding on for dear life as she ate Sandy
and got fucked and eaten at the same time.
I pulled my cock all the way out Cindy, as Sandy opened her mouth, so I slid my dick into her mouth. I felt her tongue working its way and down my shaft, and over and around the head as she sucked Cindy's wetness off of me. Then I slid it back into Cindy again, and we repeated that several times before I stood up, and walked around to the other end of the chaise and stuffed my cock into Sandy's pussy while Cindy sucked her clit. Sandy cried out as her body stiffened and she came all over Cindy's face, while her pussy nipped and grasped at my cock, as I unloaded the contents of my balls into her. Cindy sucked my cum out of Sandy, as Sandy convulsed with pleasure. Sandy then got up, and sort of staggered over to the other chaise and lay down on it, looking over towards Cindy and I. I got up on top of Cindy and slid my cock into her, and kissed her, tasting myself and Sandy's juices. Cindy held onto me, wrapped her legs around me, and we simply had raw sex, screwing wildly until she came. As she did, her pussy muscles squeezed my cock and drove me closer to yet another orgasm. I kept pumping my cock in and out of her, now up on my arms, elevated above her so I could watch my pole sliding in and out of her, as I watched her muscles flex as
she responded to my trusts. Finally, I could hold out no more and came - pumping whatever was left in
me into her womb.
I collapsed on top of her, and lay there until I caught my breath. Finally I sat up, and saw Sandy smiling at
us both, with a few fingers buried in her pussy. I swung my feet to the floor, and propped myself up on my arms. "Wow, it's so much fun watching you two" said Sandy, "you've both got so much energy. But I can't see letting anything go to waste…". She got off her chaise (only a few feet away), crawled over, and took my cock in her mouth, while she took her fingers with her pussy juice all over them and stuck them in my mouth.
She cleaned my cock thoroughly, while I sucked her juices off her fingers. She then cleaned Cindy's
pussy thoroughly with her tongue. Her phone then beeped, so she pulled it out of her satchel and looked
at it, announced that Tom was on his way back, and had to go. We watched her pull her bikini back on,
gather her towel and belongings, gave us both a kiss and said she'd probably see us later. Cindy and I
decided to head back to our room as the afternoon was coming to an end, put our suits back on, and were
soon back in our room.
After using the toilet, we turned on the shower, both got in, and soaped/lathered each other down. Before
rinsing off, we held each other close and kissed deeply. We finished in the shower, dried each other off,
and got on the bed to relax together.
"So, I thought you were feeling some serious guilt because of your having sex with Sandy, but I gather
you go over that" I whispered to Cindy. She answered, "Yes, I suppose I did. For some reason I became
comfortable with her, and all of a sudden we were having sex. When you joined in, that really did it for me.
It was so sexy to feel you inside me while she was eating me - that was incredible. I was initially upset
when you walked around and put your cock in her, but she came so quickly as we both worked her over, it
was really fun. Lucky for you, you had enough energy left over for me afterwards".
"I can't see not having energy for you" I told her "you so turn me on…".
Cindy and Sandy had one more session together while I was off scuba diving, and Tom was apparently
off playing golf. I got back to the hotel just as Sandy was getting ready to leave our room, and was
putting her clothes back on. When I walked into the room the smell of sex was in the air, and Cindy's hair
was all mussed up (causing my cock to stiffen). She had just put on a robe, which I promptly untied
the sash of, and while leering at her, pushed her softly back onto the bed. As Sandy put her clothes
back on, I took mine off, and sank my stiff shaft into Cindy's already soaked pussy. She and I both
groaned with pleasure as I bottomed out, and started to move as her body reacted.
Sandy stood there watching us as Cindy and I made lust to each other, and dropped her shorts she had
just put on. Cindy, already aroused, came pretty quickly and moved me onto my back so that she could
be on top. She came again, and then moved up to straddle my face. As she lowered herself onto my face
and willing tongue, I felt the familiar hot wetness of a blow job on my cock, and realized that Sandy decided
to stay a little while longer for dessert. My cock was soon restored to full hardness, when I felt her impale
herself upon me. I looked up, and Cindy was leaning back into Sandy, her breasts were being cupped
from behind as they both rode themselves to another set of orgasms.
Mine quickly built up as the sense of deja-vu struck me. I soon felt a few jets of hot sperm inject deeply
into Sandy's womb in a beautiful climax to the days (and weeks!) events.
The three of us untangled ourselves, and I asked Sandy if she wanted to join us for a shower, but she
declined saying that she was going back to her room, as she had to get ready for a dinner with Tom, his
golf buddies, and their wives and/or girlfriends. She kissed us both goodbye, and off she went.
Cindy and I stepped into the shower, cleaned each other thoroughly, and dried each other off (we both
really enjoy showering together when we're unconstrained for time). We made a reservation at one
of the local seafood places and rode off on our motorcycle for a wonderful dinner. When we returned
we put our bathing suits on, sat in the hot tub for a while, and made love under the stars.
We ran into Tom and Sandy a few more times during our stay in Bermuda, but all good things must come
to an end. We exchanged e-mail addresses, said we'd all meet again, and so on, but I didn't have any
Cindy and I flew home, and while doing so Cindy decided that allowing Jen and Diane to move in together
was probably the better alternative, especially given that Jen's roommate was now having threesomes only
a few feet away from her bed in a tiny dorm room. Cindy noted wryly, that if you're going to have threesomes, at least you shouldn't be directly interfering with the lives of others. And of course, I was sworn to secrecy regarding her relationship with Sandy in Bermuda (not that I'd bring that up to anyone in the normal course of conversation anyway).
I noted that Tom had told me that Sandy almost never let him participate when she had sex with women,
but Sandy apparently had no problem having me joining in with her and Cindy. The topic never came up,
and since Cindy didn't ask I wasn't going to offer any information. As far as I was concerned, however
Sandy dealt with Tom was their business. But she was beautiful, hand a killer figure, gave great head and
fucked like a wildcat. I believed that I would remember our Bermuda adventure fondly at the time.
At the beginning of the next month we hired a trailer and helped Jen move into Diane's apartment after
her roommate moved out. Cindy and the girls went out shopping for items Cindy determined were
necessary to make things a little more home-like (Diane's parents seemed strangely out of the loop on
stuff like this, but we didn't inquire), while I fixed a few things and set up Jen's bed. Then we spent a day
helping the two of them get things reorganized.
As we were driving home, Cindy noted that we might now see a bit less of Jen, now that she had a
real apartment as opposed to a dorm room. This did turn out to be true to some extent, because now
Jen was able to actually cook (she discovered what a revelation it is to have a real kitchen at your
disposal), but she still came to the house to do her laundry and just get away. After the first month, she
sent me an email noting that I hadn't been over to visit the two of them. Cindy was going to have yet
another trip in another few weeks, so I dropped her a note suggesting we all have dinner then - and
we could either eat at their place, or I'd take them out to one of the local restaurants.
Jen thought that was a great idea, so I just left it at that as I returned to concentrating on my work.