The year was 1987 and I was home on leave from the military. One particular Saturday night my parents were haveing a get together with some friends so I decided to go out and try and find someone to have fun with.
I couldn't decide what to wear until I just decided on what I thought would make me look sexy.
I grab my things and head into the bathroom and put on my sexiest black satin panties,black bra,a black skirt type garter belt and black hose and a mini one peice tight fitting black skirt.
As I am sitting on the toilet attatching my hose to the garter a man,around 50ish walks in,it was "Jacob",my parents only bi sexual friend, I don't think he quite saw right away,he quickly pulled the door shut and said the bathroom was occupied downstairs.
I replied that it was o.k. and that I would be done in a minute.
Well,I think he came to realize what he got a glimpse of and opened the door back up and smiled ear to ear.
"WOW...I never knew you had this side to you,you look sexy".
I said "thank you".
He asked if he could come in,I of course said "sure".
He closes the door behind him and asks me if I have sex with men dressed up like that?
I replied "only a few so far".
I notice a bulge staring to form in his pants and I said "I can take care of that for you if you want".
He unzips his pants and walks over and I tell him it has to be quick so no one suspects anything.
He aims his cock for my lips as I stay seated on the toilet and easily inserts it all the way to the back of my throat.
He pumps his cock in and out of my mouth,moaning oh so softly and he asks me where should he cum,I just continue sucking his hard,tasty meat.
About 3 minutes goes by and he states he is ready to cum and tries to pull away,but I grab his ass and pull him towards me,forcing his cock deeper down my throat.
I feel his cock start to expand in my mouth and the rush of cum starts spurting into and down my throat.
I swallow every drop,he zips up and leaves the bathroom smiling.
I left soon after with my bag of makeup and wigs and shoes with regular clothes over top,on the way out my parents ask me where I am going.
I tell thim I am going to spend the night a my girlfriends house and they say "o.k. see you tomorrow".
I head out to a known cruisy park and apply my make up and remove my regular clothes,put on my wig and heels and go and sit on a park bench.
It's not long before I'm being cruised by a guy around 20 or so,he walks over to me and asks me if I'm a special girl and if I was looking for a good time.
I said "sure baby,what do you have in mind?"
He said he wasn't sure and I said "well lets start slow and see where it goes from here".
I got up and led him into the park restroom and into a stall.
I unzip his pants and unleash a nice thick 8" cock.
I go down to my knees and take him into my mouth,I no sooner get him all the way in,he starts shooting cum in my mouth.
I pull him out quickly and jerk the rest off onto my black mini dress in anticipation of what I was planning later.
He apologizes and I tell him that it was fine,we can practice more at a later time,and I told him that I was only in town for a few more days and that I usually go here at some point in the night.
I stay only a little while longer,no action to be had.
I get in my car and drive by "Jacobs" house to see if maybe he is home,I see some dim lights and the flicker of the television,so I park my car and head up to his house,I knock on the door,my heart racing,hoping he is home or maybe that he isn't.
I mean what if he says something to my parents about their little slut boy?
I go to turn away and run like crazy,but it's too late.
He opens the door naked and says "damn baby,you look even better all made up and what is that on your dress? Looks like someone had some fun".
I apologize and say "I shouldn't be here" and he says "nonsense,come on in".
As I enter the house I notice an older man,late 60's sitting on the couch,cock hard and glistening.
"Jacob" says "Pete" this is the guy...er girl I was telling you about".
Now "Pete's " cock was impressive for his age,so I thought at the time. Nice and long,hard and not too thick.
"Jacob" leads me over to the couch and sits me down next to "Pete" and tells me to suck his cock while he goes and gets something.
Who am I to turn down a hard cock?
I take "Pete's cock in my hand and start licking his already wet shaft up and down and stroking it with my hand.
I occasionally take him in my mouth,switching back and firth between licking,stroking and sucking.
His salty pre cum tasting very sweet.
"Jacob" comes back out and I notice he has a video camera and he is recording me,I don't even care at this point,I continue to please the man attatched to the cock in my mouth.
"Jacob" then sets up the camera on a tripod and puts the lights on full power,lighting up the room and I notice his windows are wide open and his curtains fully pulled back for the whole world to see and hear.
Too caught up in the moment to care,plus it's fairly late anyway.
"Jacob comes over and sits on the other side of me and now I take turns sucking both of their cocks.
All the while my cock straining in my panties under my dress.
Their hands rum up and down and all over my body,talking to each other saying how good a cock sucker I am.
"Jacob" ask me if I have ever had sex in a sex swing before and,not nkowing what it was I told him no.
He gets up,goes into the bedroom,comes back out with this contraption and hangs it right in front of his huge bay window.
He starts to pull the curtains and I stop him and tell him to leave them open,so he leaves them open atleast 3/4 of the way.
He stands me up and leads me to the swing,and gets me situated in so that I am comfortable.
I am now at a good height for their cocks to enter me.
"Pete" goes first,applying lube to his cock,he has to slide my panties to one side because they were under the garter.
He slides his cock in nice and slow.
I feel the head press against my ass first and then the shaft sliding in.
He lets out an "OH God this is FANTASTIC!"
I oan my approval as well as he slowly pumps his cock in and out of me.
Jacob walks towards my head and inserts his hard cock into my mouth.
I am in pure extasy,one man fucking my ass and the other fucking my mouth.
They both take turns,playing switch.
"Pete's" fucking me then "Jacob" and back and forth for probably 2 hours.
Everyone sweating and moaning.
Every now and then a car would go by the window,making me hornier and hornier thinking they could have seen what was going on.
At this point "Pete" is ready to cum,a few more thrusts and he pulls out,shooting a huge stream of cum all over my dress and hitting mme in my chin as I continue to suck "Jacob's" cock.
As "Pete" finishes,"Jacob" gets bewteen my legs as I sway back and forth in the swing.
He shoves his cock into my ass and starts pounding me like no tomorrow.
Saying how he wanted to fuck me for a long time and I told him he should have acted on that impulse.
"You were too young" and I would reply "old enough to fuck a man like you".
I told him to just close his eyes and go back 8 years when I was 14....
He closes his eyes and starts pounding me harder and harder and harder.
My moaning getting very loud now,anyone walking by outside could not only see they could hear.
"Come on daddy,fuck me" i tell him.
I think that was all it took,he couldn't even pull out.
He just lets loose with a load of cum deep into my ass.
As I feel his cum spurt into me I expolde in my panties,still covering my cock somehow.
As he pulls his cock out cum drips out of my ass and onto the floor.
Both "Jacob and "Pete" help me out of the swing,I ask if I could take a shower and that my parents didn't expect me home tonight.
They both smiled and said "no problem" almost in unison.
"Jacob asked if I would sleep in something sexy and with my wig and I of course said "yes".
After the shower,I put on a sexy red teddy,red thigh highs and matching red panties,my blonde wig and went and layed in the bed between them.
We all kissed good night and fell asleep.
About two hours later,"Pete" wakes me up,his cock is erect.
"Pete" I find out is not awake.
I gently move under the covers and take him in my mouth. After a few minutes of sucking this sleeping mans cock,his hips start to move and I know he is awake.
He slides the covers back and I hold my finger to my lips and say"shhh".
As I am sucking his cock,I reach down and slide my panties off,I then quietly move up and get ontop of "Pete" and grab his cock and glide it into my ass.
I bend down and whisper in his ear,to be quiet.
As I am laying ontop of "Pete" I slowly,very slowly move my hips back and forth,just enoough to get his cock going in and out a little.
We fuck for twenty minutes when I am rewarded with another impressive load into my ass.
I lay there as his cock goes limp in me and soon I roll off and slip my panties back on and we both fall asleep.
The next morning arrives and "Jacob" is all over me.
"Pete" has gone home already.
"Jacob" waste no time and lubeing up my ass.
Say's we have to hurry,his ex wife is coming over soon.
He pulls my panties down,throws my legs up in the air and slides his cock into my moist ass.
Ten minutes and he is cumming in my ass again.
He pulls out as his wife rings the door bell.
He says for to wait a minute'he'll be right there.
I put on my dress and panties from last night,he answers the door,I grab my bag and walk right by her.
She says to "Jacob" "isn't SHE a little too young for you".
And she knows me from going to my parents house when her and "Jacob" were married and she didn't even know.
I think I ended up spending more time with "Pete" than "Jacob",but they both had their fair share of me.
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<a href="https://www.lushstories.com/stories/crossdressing/my-parents-friend.aspx">My Parents Friend</a>