First time cd crossdresser with daddy at pool

First time cd crossdresser with daddy at pool
A Day at the Pool
One of my buddies and I were at his dads house doing what most
unemployed graduates do, laying around being lazy smoking pot. We had just
bought a bag and a six foot bong and were smoking it for the first time.

We had no idea what to expect from the bong and my buddy, Ted,
jokingly said to me ‘Ryan if you can’t take the whole bong you’re a pussy
and have to wear a bikini around the pool all day’.
I laughed and responded ‘okay, but if you can’t you’re a bigger
pussy and have to wear a dress to the gas station to get us smokes ‘.
So with our little bet we packed the bong and he went first. I
actually was surprised as the bong filled up that we even thought that we
could finish it. Then ted cleared the whole thing and I was even trying to
make him laugh to fail the whole time.

It was my turn and I figured he did it with no problem that I
shouldn’t have one either. I started and about half way though I just
couldn’t go any further. I tried my best but was coughing and had to stop
and as soon as I stopped Ted was laughing and said ‘I’ll find you a bikini’
I didn’t think he was serious and finished the rest of the bong
without much thought.
Now I was way high and he looked at me and asked ‘Do you care what
bikini I should grab you?’
I laughed and said “the hell I’m going to wear a bikini and you
don’t have one anyway. ‘
He looked me in the eye and said ‘You made the bet that I was to
wear a fucking dress you sure as hell going to wear the bikini and my dad
has a bunch of shit from when his last girlfriend walked out on him.’
I guess I was pretty stoned and didn’t put up any more fight and
followed him into his Dad’s room. His dad was a pretty cool guy and that is
why we hung out at his house. He usually didn’t care if we smoked or drank
and he had a pool. Plus the house was in the middle of the woods and
pretty secluded from any neighbors. It made for some fun parties in high
Ted showed me the dresser in his dad’s room and told me his Dad’s
last live in girlfriend, Janet, just up and left. They must have had on
hell of a falling out since she never came back for any of her stuff. He
open the bottom drawer and told me I could choose the suit myself while he
I looked at the drawer and there was a mess of color. I pulled out
the top and it was a little purple bikini top. There must have been five
suits in there and I dug around until I found the only one piece.
Ted looked at me and said ‘that’s not a bikini, you have to wear a
While he sat on the bed I found the only one that had some moderate
coverage and a full size bottom. I guess it wasn’t too bad since it was
like a Speedo but it was hot pink and there was a triangle top that
Ted was laughing and said ‘Why don’t you grab a joint and go get
dressed. I’ll meet you by the pool.’
I did as he said and grabbed a joint from his room and headed to the
bathroom to change. I sat on the toilet and smoked the whole joint myself
and by the time I was done I really thought it was a great idea to put on
the suit and strut my stuff. If I had to do it I might as well have some
fun. I stripped and put the bottoms on which weren’t anything different
but the top felt a bit silly. I looked at myself in the full length mirror
and thought the bulge in the bottoms looked a bit off so I reached in and
tucked my cock between my legs. The suit was snug enough that it held me
back in that position very well. I felt almost ready to go and peeked out
the door.
I knew Ted was going to see me eventually but I still felt a bit
odd to be in a bikini. So I snuck back to Ted’s room and had another hit of
pot. After that I thought maybe I could have some fun and went to his
dad’s room to accessorize a bit. I looked around and found a robe and some
heels that actually fit me. I figured I was ready finally and headed out
to the pool.
Ted was lying back in the sun when I walked out and he turned
around and gave me a wolf whistle. I blushed a bit but walked over to him
and asked him ‘You like what you see?’
Now that brought a big laugh out of him but he did say ‘you really
don’t look too bad in a bikini.’
‘Here have a drink’ and he offered me a drink that looked like ice
tea and told me ‘Take off the robe and enjoy the sun’.
So I took off the robe and sat down and tried the drink. I guess it
was no surprise that it was a long island tea and I felt I deserved it. We
sat there for a bit in the sun with the cocktail and had a smoke.
The sun felt great and the mixture of pot and booze had me feeling
After awhile Ted got up and dove in the pool, I was hot also so I
followed him in. It actually felt good and the bikini top really didn’t
make any difference. We swam for awhile and then returned to the chairs to
relax more.
We’d been out there for about two hours and were swimming in the
pool again when we heard Ted’s Dad, Frank, on the pool deck. He was
laughing when he asked us ‘Is this how you boys usually spend your time
when I’m out?’
I must have turned bright red and Ted said right away ‘Nah, Ryan
lost a bet and this is my punishment for him’
Frank smiled and said ‘Hell you look better than Janet did in that
suit. Mind if I join you boys by the pool, it’s such a nice day’.
Seeing it was his house there wasn’t anything we really could say,
we invited him to join us.
He looked at me and said ‘keep that suit on and I’ll be right out.’
About five minutes later Ted and I were laughing about the whole
situation when Frank came out. He had a towel and a drink himself. What I
didn’t notice was he also brought a camera. After he set his stuff down he
came over and took some pictures of us saying ‘I have to get this for my
scrapbook ‘
That sort of sobered me up but he must have seen the fear in my
eyes since he laughed and told me ‘relax Ryan, and enjoy yourself. Why
don’t you two come out of the pool and have a drink with me’.
We both got out but he took the camera again and kept getting pics
of me. I told him to stop but he laughed again and told me ‘come and sit
down and be more ladylike. ‘
Finally I figured ‘what the hell’ and did some poses for him and
said ‘you might as well get my good side’.
We all laughed and had some more to drink together. We all went for
a swim for awhile and Frank bumped into me often, probably more that
necessary. He actually was wrestling with both of us but I felt as if his
hands were on me most of the time. I really didn’t mind and didn’t try to
avoid it either.
Frank got out and said he’d make us some lunch.
Ted and I continued to swim while he went into the house. Frank was
back with a plate of food and told us to come and eat.
He really was a good Dad making us lunch and all. When I got out he
handed me my towel. After I dried I was about to wrap the towel around
myself when Frank came over and held my robe open for me. I figured he had
seen it and I should put it on as offered.
He told me as I put it on the robe that my shoes were right over by
the table and I didn’t need any more of a hint that he expected me to put
those on too. I figured it wasn’t a big deal anymore and put the heels on
and walked to my spot at the table. We all had lunch together and a little
small talk. We were all done eating and Frank came back with another round
of drinks and sat down with us again.
When I had my first drink he asked Ted ‘what time are you supposed
to be at your Moms place for your weekend getaway?’
I didn’t know anything about this so I didn’t think much of the
question. But I guess Ted did since he got right up and headed to the
house mumbling the words ‘shit, I’m late’.
Frank looked at me ‘Ted was supposed to be at his Moms place at
least an hour ago for a little trip out of town.’
I didn’t know what to think but Ted was back dressed in no time
and he told me he had to run since he already was in huge trouble. He said
bye to his dad and he was off.
Now this was not the situation I had ever thought I’d be in, sitting
by the pool with my best friends Dad wearing a bikini. Not just a bikini
but a silk robe and heels. Frank must have seen my apprehension.
I stood up and told Frank ‘I should be going too’
Frank immediately replied ‘you have a full drink and it’s a
beautiful day, you couldn’t leave yet’.
I felt awkward but sat back down and we sort of chatted and enjoyed
the sun with our drinks.
Frank said he had to run inside and would be right back so I sort of
relaxed and had a smoke while I waited. I was feeling a little more
relaxed since I actually felt like we had a real conversation and it wasn’t
me just talking to my friend’s dad. I never thought I’d almost feel like
an equal instead of a k** but I guess that is what happens as you grow up
and graduate high school. I must have been really absorbed in thought
because Frank appeared and snapped me back.
He had two more drinks for us that I tried to nicely decline but
again he said we were having a nice time and he really enjoyed my company
by the pool. I was enjoying myself too by this time so I stopped putting
up a fuss.
He did point out that I was getting a little bit of sun and he
produced a bottle of suntan lotion that he said I should put on. I agreed
that was probably a smart idea especially since I didn’t need to get a
bikini tan line.
He chuckled saying ‘it probably would look pretty hot if you did’
and he squirted some lotion in his hand.
I had thought he was going to give me the lotion but he told me
‘come over and sit down in front of me so he could lotion you up’.
I didn’t know what to say but I guess I hadn’t thought about him
ever putting lotion on me. But I also didn’t have too much apprehension so
I went and sat down in front of him and he started to put the lotion on my
Man did the lotion feel nice as he put it on for me. His hands were
sort of massaging it into my shoulder and then he moved to my back. I just
closed my eyes and enjoyed the massage. As he finished up my back he made
sure to not miss any spots which made his fingers slip a little into my
swimsuit which sort of caught me by surprise.
I still was enjoying the feeling of his big hands on my back when
he said “okay young lady your backs all done now let me get your arms.”
I didn’t protest at all but thought I could take care of those
myself but as he worked the lotion on my arms I sort of lost my mind
because I really was enjoying his attention. This must be what it is like
to have a real massage I guessed. He finished up my arms and had me sit
back and he started on my feet and worked up my legs.
Now I was getting a bit nervous since on my back he didn’t miss a
spot and my legs went all the way up to where I never thought a guy would
ever touch. But it felt so good I didn’t even flinch as he kept going. And
when he got to the top he gently slipped his fingers just barely into my
swimsuit and I couldn’t help myself but enjoy his touch down there.
God I must be crazy because it felt so good to be touched by him
this way. It must be just what a massage feels like;’ I’m going to have to
get a massage’ I thought.
Frank said ‘stand up so I can could get your stomach’
So I stood and he sat down in front of me. I know he was talking
but my mind was elsewhere as he smoothed on the lotion on my belly working
around my bikini top. I almost told him he could reach in my top to coat my
breasts since my nipple were tingling and I wanted them to be touched but I
resisted that urge since that would be really weird and this was a just him
being nice.
Well he finishes and I didn’t really want his hands to leave but I
knew I had to be polite and I said ‘thanks for putting the lotion on me. ‘
He said’ it was my pleasure and you can return the favor’
So I got up and told him to have a seat as I grabbed the lotion.
I wasn’t sure what I was doing touching another man but he had just
put it on me it was only fair to pay him back. I squirted the lotion on his
back and started to rub it in. I had never really looked at his body
before but he was pretty fit and had a very nice build.
I was massaging it in getting to feel how developed his back muscles
were and enjoying touching him a bit. I knew it was just admiration. I
moved on to his arms after I felt like I had gone over every inch of his
back. I worked it into his fingers and all the way up his arms. I didn’t
have him move around like he had me but I moved myself around to reach each
area. As I worked each arm he would rest his hand on my butt. I thought
that it was an odd area for him to need to rest his hand but I didn’t react
since it felt nice and I actually moved to maintain his hand in that
position. I don’t know why but I made it easy for him to keep his hand
I finished his arms and asked ‘lie down and I’d take care of your
I really wanted to do his chest since I wanted to feel his muscles
after feeling his back but I thought that would be odd again so I figured
I’d do the same routine he did for me. Keep it the same just a couple of
guys putting lotion on each other. Girls do it all the time to each other
and this is no different. So I had him lay down to do his legs.
He opted to sit in the recliner by telling me ‘you can do a good job
if I sit this way for you’ and kept his legs sort of bent up which made it
easier for me, maybe I should have sat that way for him but I hadn’t
thought about that when he asked me to lay down. After he got comfortable
I picked up his foot and started to rub the lotion in. I tried to do just
the same he did to me as he worked up my legs. He was very gentle but it
felt soothing so I tried to mimic his work. I figured it would be easier
for me since He had loose shorts on and I wouldn’t feel weird about
reaching into his swimsuit like he did mine.
He never touched me where he shouldn’t but he didn’t miss a spot
either. As I was working up his leg he lifted his foot and I was looking
where I was going next and I realized I could see right up his shorts.
Uhh, I wasn’t expecting that and there is something else, He wasn’t wearing
swimwear but just loose short with no underwear. I could follow his toned
hairy legs all the way up his short and I could see his balls.
Man they looked big and I couldn’t take my eyes off of them. I know
I shouldn’t be looking up his shorts but I couldn’t stop and I didn’t know
how far I needed to go with the lotion.
Well I did the best I could but when I got up to his shorts I sort
of chickened out and stopped right at the hem of them. I didn’t say a thing
but moved on to his next leg and I couldn’t help but to look at his shorts
again. But I couldn’t see anything and I was happy about that as I worked
on his foot.
He then lifted his leg so it would be easier for me but that just
opened his shorts and this time I couldn’t see his balls but I could see
his schlong! My god what am I doing I had to ask myself. I didn’t stop
since I didn’t want him to know I could see up his shorts.
I tried not to look but found myself intrigued. He was so big
compared to me and he looked like he wasn’t circumcised. It looked so nice
and smooth. I worked my way up his legs and actually didn’t stop at the hem
this time. I had an urge to just touch it to see if it felt as smooth as it
looked. But I chickened out again or got my senses back and stopped just
after the hem.
And as I took one last look at it I could swear that it had grown
bigger, I wondered ‘how big does it get and was this turning him on’.
I had to admit I felt turned on even with another man. I guess he
towered over me so I told myself it was normal admiration.
I told him he had to ‘stand up so I can do your chest’
But he said ‘you can just straddle the chair and sit on my lap to
get my chest’.
Now after looking up his short for so long I knew what was in there
but I figured that was the easiest way for me to get his chest anyway. I
got up and straddled his body and the chair, I figured I’d just hover in a
squat and do his chest quick but as I hovered initially I started to lose
my balance and Frank caught me and said ‘it’s ok if you sit’
Well not only told me but used his hands to guide me to sit right in
his lap. I knew exactly what I was sitting on and found it strangely
interesting. I could feel his length and the direction it was
pointing. Well maybe I couldn’t actually feel it that much but from looking
at it I knew where it was. I just sat there and started to work the lotion
into his chest.
As I was admiring his muscles I was rubbing him all over his chest
which made me sort of squirm in his lap. I was enjoying it as I moved
around feeling where his manhood moved as I moved. I admit it was pretty
gay but it was fun and he didn’t say anything. But as I worked my way to
his stomach I had to really move and bend I noticed that something had
I could feel he was getting hard. Oh my god I didn’t know what I
should do. I was almost reaching into his shorts to put lotion on and I
could tell he was getting hard. I actually didn’t know what I was doing
because I didn’t stop anything either, I kept on moving my hips around
which kept rubbing his growing bulge and I was sliding my fingers into the
top of his trunks.
I looked up to see his face and he had his eyes closed but a smile
on his face and my hands were following his shorts to the center. I sort of
reached a little further and I could feel the top of his pubic hair.
I slowly finished that spot and took my hands out to announce
He reached up and grabbed my hips because I stopped moving and he
sort of kept me moving with his hands and told me’ that felt beautiful’.
Finally he opened his eyes and smiled more as I decided that I
should get off of him before something weird happens. I don’t know what
would be weirder that what we had just done but he let me off and told me
‘lay back and I’ll get us some new drinks.’
I quickly agreed since I was a bit flushed from what I had just
done but I watched as he got up and walked away, and there was no denying
it, he had one massive hard on. I actually couldn’t say much since I was
tucked between my legs which prevented mine from showing but I was
outrageously aroused. I knew that him getting me another drink meant I
wouldn’t be leaving until we finished but I promised myself that would be
the last drink and I’d get out of there and be out of this silly bikini
that I was wearing.
Frank came back with our drinks and we both laid back to enjoy the
day. We didn’t say much for awhile as I think we both needed to cool down.
When we finally talked, Frank was offering to light me another
cigarette, how gentlemanly of him. We chatted more and he made the comment
of how lucky we were to have a day like this together.
I agreed that the weather was too nice to waste but I’m not sure if
that is what he was talking about.
Over the years we had known each other by him being Ted’s Dad but
now we were having a real conversation. He asked me about my likes and
dislikes and told me about his. It was as if we were equals or friends, I
really liked the feeling of being friends with Frank.
It had been over an hour since we laid down and it was getting
hot. Frank suggested we go for a swim but I declined. He got up and dropped
the lotion by accident next to me. As he reached down to pick it up he
reached under me and picked me up and headed for the pool.
I put up a little fight but he said we both needed a swim and
jumped in with both of us. Well that was a shock when I hit the water but I
squirmed out of his hold and turned to try and dunk him. Frank swam away
and it turned into a fun game with a lot of body contact.
After tiring out we were sort of leaning into each other and I
noticed that Frank’s hands were sort of massaging my ass. I know I enjoyed
our last massage but I knew I should make it stop but all I did was gaze up
into his eyes, which I had never noticed before that they were a light
shade of green. I thought they were pretty sexy eyes and as I gazed our
faces kept getting closer.
His hands on my bum and I was feeling his chest. I didn’t want any
of this to stop but I didn’t want any of this to happen so I quickly moved
away from what almost felt like a start of a kiss and got behind him.
I thought it would be funny to pull down his shorts and I quickly
pulled them to his ankles. As I swam away I felt his big hands grab me and
we had a fun little struggle.
He didn’t pants me like I did him but got me in a bear hug and
worked his hands into the top of my suit.
I know it shouldn’t matter since I’m a guy but when someone feels
you up in a bikini it is just different. As soon as he found my nipples and
pinched them both between his fingers a lightning bolt shot through my
body. I just leaned back onto him as he caressed my breasts.
I reached back to pull him into me even closer, but as I reached I
didn’t grab him but found out he never bothered to pull his shorts up and
my hand grabbed the first thing sticking out. And you that was his cock. My
breast felt so good and I didn’t think what I had in my hand but just
grabbed it and sort of moved my hand to figure out what I had. Even when I
realized that it was his cock I didn’t let go but kept a hold of it.
At that same time I felt him kissing at my neck. What a combination
of feelings, my breast being gently caressed while getting sensual kisses
on the neck and having a great big handful of man sized cock. I just
enjoyed it as he worked up towards my ears which made me turn my head
towards him. As soon I moved towards him he moved his kiss to my lips.
What was I to do? I melted into him and slowly accepted his kiss.
I guess with the drinks I had I had lost all of my inhibitions
because when he stuck his tongue into my mouth I did nothing to stop
him. It had also been a long time since I had a girlfriend and it just felt
I turned towards him to straighten my neck out and my hand never
left his crotch. I was so excited I was stroking him as if it was my own
and it felt so wonderful.
We made out for ever it felt like and when Frank finally let up he
said to me ‘I’ve been wanting to do that since the second he saw your cute
little ass in this bikini’. Then He asked ‘is everything okay?’
I told him ‘I have no idea what ‘I’m doing but I don’t want to
With that comment he continued to kiss me and I kept stroking
him. His hands moved all over my body both on top of my suit and inside of
it. When he rubbed my crotch with my cock restrained I thought I was going
to cum right then but he moved on and just had me at the edge. I couldn’t
believe how hot I was and when he turned us around so his back was to the
wall I didn’t know what was going on
But he broke our kiss and told me ‘I’m so hard I’m ready to explode
but I don’t think I can by just being jerked off.’
I must have looked like a deer in headlights because I had no clue
what he meant until he pulled himself up onto the edge of the pool and I
was staring straight at his cock. I know I had already seen it but that was
by accident and this time it was inches from my face. I was still holding
it and I let my hands both explore freely. I cupped his balls and looked at
his uncircumcised cock as I moved the skin around. I had never seen one
this close or this big actually. I was mesmerized and I played with it like
a new toy, which I guess in a way it was.
Frank had laid back and spread his legs so I had free access to
him. After awhile I had the distinct urge to taste him cock. I suddenly
thought it was gay to be touching another man but then again I had been
playing with him this long so I guess I had stepped over that line a while
ago. Once I made that decision in my mind it didn’t much for me to decide I
wanted to taste him.
I looked up to his face which was laid back eyes closed and a huge
smile on his face. I reached my tongue out and just touched the tip. Now I
didn’t know what to expect but I got a low moan from Frank and he let me
know how good that felt. I got a little braver and explored him with more
of my tongue. I tasted his balls, licked the shaft and even stuck my tongue
into his pee hole and wrapped his extra skin up my tongue to see how that
I was really enjoying my exploration and the encouragement from
Frank made me try new things. It didn’t take too long before I had the head
in my mouth and wondering how much of his cock I’d be able to get into my
Not that it was a challenge that I needed to do but I tried to get
as much into my mouth as possible. I kept hearing Frank saying things like
‘oh god yes’ which made me try to get more.
After I’d gotten almost all of it in my mouth I felt his hands on my
head and he started to control my speed of sucking. He was really moving my

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