Date: Sun, 16 May 2021 15:41:55 -0400
From: Drew Hart <drewfhart@gmail.com>
Subject: My Adventures as a Bi Male Part 10 bisexual/encounters

Part 10

In 2005 the company I was working for sold and I received a big payday
for my stock, I also started to receive job offers and decided to leave
for a bigger opportunity with a company. It was also around the time I
was turning 30 so I planned it out to have a month off between jobs since
I have not had a break since high school since I went right into college
and worked every summer. I planned 3 weeks of vacation 1st flying down to
Florida and going on a cruise for a week, to be followed by flying to a
resort for 2 weeks, then back home for a week before starting the new
job.  The 1st week on the cruise was fun, it was a singles cruise week
and I did a lot of hooking up with just females getting laid the entire
week, but no bi sex. I got off the cruise back in Florida and flew right
to a resort for the next 2 weeks. The 1st couple days was similar to the
cruise I hooked up with single girls and relaxed which is what I needed.
A couple days into the trip while relaxing I met a couple Bob and Jill
there for their 20th anniversary and were both 42 years old. Jill was
about 5-6 120lbs long blond hair, and Bob was in shape about 5-11 salt
and pepper hair.  We had some good conversations over drinks and agreed
to have late night cocktails together. That night we met for drinks and
had a good time, and at what point Bob went to the restroom and Jill
mentioned that Bob was going golfing the next day, she winked and said he
would be gone in a couple hours as I was interested in getting together
with her in their room. I was taken back at 1st and said wow nice offer
and you are hot but not sure how smart that is with Bob here and I
rejected her offer with her being upset by the rejection. Bob returned
and they left to go back to their room.  The next day I was having a late
morning cocktail when Bob approached me, he had on his golf gear and
grabbed a drink before the shuttle was taking him to the course. Before
he left he said he and Jill agreed to have a fantasy week and what
happens on the island stays on the island, he knew what she asked me last
night because he is the one that approved it and said please reconsider
her offer while he is gone.


I sat there drinking and was shocked by this but also very interested
now, 30 minutes later as I was laying down Jill came and sat next to me.
We talked, had drinks and flirted with each other, eventually making it
into the pool where we messed around and finally kissing while she
grabbed my cock through my trunks. We got out and had another drink
letting the sun dry us as we continued to flirt and even kiss, finally
she said are you going to fuck me or what. I wasted no time as we headed
to her suite where we spent the afternoon giving each other oral and
fucking each other multiple times. We made our way back outside grabbing
drinks as she continued to flirt with me and kiss me and then Bob
appeared after golfing all afternoon. This didn't stop Jill as she
touched me kissed me in front of Bob and then they left saying they had
to get dressed and have dinner and we agreed to have drinks late at
night. I went back to my room and fell asleep for a couple hours after
all the action. Once I got up I showed, dressed and made my way back to
the bar area outside and had dinner and drinks. Later in the night I was
approached by Jill who gave me a hug and invited me over to her table
with Bob, she looked very hot in a nice tight dress.  Once I sat down
Jill sat very close to me with her hand on my leg and taking mine and
putting on her leg. We had drinks and talked about Bob gold and some
sports, after about 30 minutes Bob got up and said he was heading back to
his room, as he left he said have fun as he winked. Jill and I had
another drink and talked about our afternoon, my hand made it between her
legs feeling her soaked pussy. Jill then went on to tell me that when her
and Bob left earlier they went back to the room where she told him about
what they did as he fucked her which was the best sex they ever had based
on me warming her up for him. She then said he wants me to go back with
you for a midnight session, but with one condition, I asked what that
was. At this point I had a finger in her pussy and her hand was rubbing
my cock, she leaned in and kissed me then whispered in my ear that he
wants me to cum in her pussy so he can feel it later. We almost ran to my
room where we had a fuck session for the next hour with both of us coming
twice, and me both times in her pussy. After the 2nd time she got
dressed, kissed me and said she will meet me tomorrow and left.


The next morning, like the previous day I made my way to the bar for late
morning drinks, I had lunch and relaxed but no sign of Jill or Bob. A
couple hours later I saw them getting off a shuttle where they must have
gone on a trip. Jill came over to me and said will I be here for a bit
and I said yes, and she said good she will be back in 30 and gave me a
kiss and left. She returned as she said and had a drink with me then said
will I take her back to her room for a nice afternoon snack, and off we
went. We got back to her room and I was taken back. There was Bob wearing
only panties with his arms and legs tied to a chair, and also gagged. The
chair was in front of the bed in the room where Jill sat me down there
and we kissed and made out like two teenagers. After a couple minutes of
this Jill pulled me off the couch so we were both standing right in front
of Bob, she pulled off her bikini and she grabbed me to suck her nipples,
she then looked at Bob and said you want me on my knees, and he just
shook his head yes, as she fell to her knees and lowed my trunks
releasing my cock ad Bob moaned into his gag. She took my cock and looked
at Bob again and said honey this is the cock that's been fucking your
wife, and with that she took my cock in her mouth while her husband
watched. With this scene I didn't last long and after a couple minutes I
exploded in her mouth while she took it all in her mouth while Bob
watched on. She kept sucking me, and rubbing my balls, getting me hard
again and then led me to the bed where she positioned us so Bob could see
us perfectly as I fucked his wife. Since I came already I was able to
last a while as we fucked in many different positions, also Jill was very
verbal making comments about how my cock was bigger and I fucked her
better than Bob. I finally came in her as we laid next to each other
catching our breath, she made a comment saying that was the best fuck I
ever had. She then asked me would I please untie Bob if he has to do
something. I went over and untied him, he got up, took the gag out and
went right into the bed as Jill spread her legs and he ate my own cum out
of her pussy. I stood there watching Bob eat cum out of his wife's
pussy, my own cum, she verbally called him names, saying this is what he
always wanted to do. As I watched I somehow got hard again and Jill
noticed this, so she motioned me over to lay on the bed. She changed
positions, getting up on all fours as she instructed Bob to eat her out
from behind and sucked my cock. After about 5 minutes Jill let my cock
slip out, and looked at me and asked me can my husband suck your cock. I
was so horny I nodded my head and Jill rolled to the side and said pussy
boy suck his cock until he comes. Bob took my cock in his mouth and gave
me a good blow job, I could tell this wasn't his 1st time but probably
hid from Jill, based on her talk saying this is something he always
wanted to try. I lasted about 5 minutes before I exploded in his mouth
with him taking it all since it wasn't that much since this was my 3rd
time.  I got dressed as they laid on the bed and I left.


That night I didn't see them so I just hung out alone at the bar having
drinks and relaxed listening to music. The next day I didn't see them as
they probably went on a trip. I relaxed all day catching up on rest and
enjoying the drinks and weather. I went back to my room around dinner
time, to take a shower and as I got out there was a knock on the door and
it was Jill dressed very sexy, I let her in and she gave me a kiss and
asked me if I wanted a date for the night, to which I agreed. We had a
romantic dinner on the beach which she setup followed by a show we went
to back for drinks and then back to my room where we had a couple hours
of amazing sex and then fell asleep. We woke in the morning, which led to
a fuck session which the led to the shower where we fucked in there and
back to the bed where we talked about our amazing night. It led to us
talking about the other day with Bob sucking me and asking was I into
that which I told her I was Bi and enjoyed it. She liked hearing that and
asked if I was up for it again, and I said I think I could be convinced.
She said she was going for a spa day all afternoon, can I please take
care of her husband's fantasies, I said maybe she kissed me and said she
had to go and leave.  I went to the bar around my normal time and shortly
after noon Bob came up to me and we had drinks. After a couple drinks I
said to Bob that wasn't the 1st time you sucked a cock the other day was
it. He said no it wasn't but Jill didn't know, he went on to tell me he
was BI and had his 1st experience with a coworker a couple years ago, I
told him about myself also, and then we headed to his room. Once in his
room we hopped into the bed into a 69, and then he begged me to fuck him,
he had lube but no rubbers and my thought process was I have been fucking
his wife bareback wo oh well. He was a good fuck, nice and tight, and
after some time I was ready to come and asked him where he wanted it and
he yelled in me so I unloaded in his ass. We then headed to the shower to
clean up which then led to kissing and oral in there until we were back
in the bed with me fucking him again, until Jill walked in. All she said
was this is hot as she removed her clothes and got on the bed so Bob can
eat her out while I fucked him. After a couple minutes of this she said
don't come to me, and to pull out. I pulled out as I was standing there
and Jill told Bob to clean my cock off and give it to her, Bob obeyed and
sucked my cock, then led me to the bed where Jill was laying there with
her legs spread, Bob took my cock and guided it to her pussy pushing m
cock into his wife and then kissed me and said please fuck my wife. I
fucked Jill hard for the next couple minutes until she came and I came in
her pussy. As I pulled out Bob jumped right in to clean her pussy out. As
I was leaving they said they both wanted to have dinner with me tonight,
I agreed and met them for dinner, and afterwards drinks and music. It was
getting late and Jill said she was tired from fucking me all night and
her spa day so she was calling it a night, she gave us both a kiss and
said try not to have too much fun. Bob asked was I up for some more
action, and I said I was but I need help now, he asked with what and I
said I have been taking care of you too but I am in need of some fucking
to me, and grabbed his sock thru his shorts and said how about this in my
ass tonight. He didn't need to be told twice and we headed back to my
room, where we 69 and he fucked me bareback twice coming at me both
times.


The three of us played for the next couple days until they left a day
before I left, we lived back in the states I on the east coast and them
in the middle of the county. We exchanged information promising to keep
in touch and me thinking we never would but we did. As I write this story
this encounter took place 16 years ago, and we get together to this day a
couple times a year and vacation together which has led to many amazing
encounters which I will share later on. What a Great vacation.


Part 11 to Cum