Three's Company

Another great feeling/accomplishment. An older, gorgeous woman.
She definitely knew how to suck. She stroked me and took breaks, examining my dick. I came for what seemed like 30 seconds. She kept her lips locked on.
She got up and suggested we go to her bedroom.
She stripped as I watched. She had neck length red hair in a professional cut. She wore pink lipstick. She kept herself in great shape and had smallish titties that were shapely. She had freckles over most of her body and trimmed her pussy.
We moved to her bed. Her apartment was furnished nicely.
She stroked my dick as I examined her body.
"What's your name"
'You're beautiful"
"You are also and you have a huge dick"
I started reciprocating her blow job. I slide her lips apart and gently sucked on them. I played with her lips and her clitoris.
She ;pulled my face to hers and said
"I want you to fuck me"
I gave her what she wanted.
Afterwards we laid there again and she panted
"Wow, that was incredible"
I was embarrassed again.
"Is there anything you want to do?" Jennifer asked
"I haven't fucked anyone in the ass yet"
"I've never done that"
"It's not important"
"NO, your dick is incredible, I'll give it a try"
Jennifer got up, went to her bathroom and returned with some KY-jelly.
"lube me up first"
I spread some of the jelly on my finger as she rolled over
Jennifer has great ass. She didn't sag and she worked out each day. I just stared at this lady that was 5 years older.
I spread her pretty ass and rubbed her anus with my finger. She spread wider ane moaned.
I worked my finger in. She moaned more
I worked that finger in her for a few minutes and then slid in a second.
It seemed like she should be ready so I pulled out my finger and slid between her legs.
I spread apart her cheeks and guided my dick towards her ass.
I got my dick head up against her anus and gently pushed.
It was difficult and I didn't make much progress. I waited and pushed again.
After about 5 minutes of gently pushing I was only in an inch.
Jennifer pulled forward and rolled over.
"This isn't going to work. Is there something else you would like to do?"
I thought about it for awhile.
"How abut some pictures"
"Nude pictures of me?"
"No way, they will make it to the internet> I'm engaged"
We relaxed a bit and I looked around the room. She had some office equipment and it was apparent she did some work at home.
"What if i take them with your camera or phone, we print them on your printer and you can delete the files.
"Okay, that will \work"
I couldn't believe it. She posed for me any way I wanted. It's a bit funny though, the ones I like the best are the classic poses, not the raunchy ones.
She got a wash cloth and cleaned my dick and we fucked again.
"Keep this quiet, I don't need my finance finding out"

I thought by now I had experienced everything I ever would.
About a week later, after I had fucked and sucked with Susan I headed to the bathroom again. After I was done I went into Jimmy's room and grabbed him.
We went into the hallway.
"What do you want?" Jimmy asked.
"I want you to rim my ass while I fuck Susan"
"Yeah, I don't think so" a he looked at my dick
"Come on Jimmy"
We talked about it for at least 20 minutes and he finally agreed.
"Come over her to the bathroom" Jimmy said.
He ran a wash cloth in the sink and rubbed some soap on it.
"Lean against the counter" he said
I turned away from and leaned against the vanity as he directed. He took the cloth and started scrubbing my ass. He spent at least 5 minutes cleaning my anus.
I went back into Susan's room and started rubbing her. She was always reading and in no time I was fucking her again.
Jimmy slowly came in the room and gently made it onto the bed and between my legs. I was getting excited.
He slowly lowered his head and I could feel his breath on my anus. Then He gently ran his tongue around my rim. What a feeling. I was fucking his s****r while he rimmed me. I came almost immediately.
Jimmy tried to get up and leave.
"Hold on Jimmy" Susan said
"I want that too"
Neither Jimmy or I could believe what we heard
"Are you sure?" I said
"Yup" said Susan.
She grabbed my member\
"How soon can you be hard?"
"I don't think it will take long, give the circumstances."\
Susan played with me as I looked at her beautiful body. It didn't take long.
Susan pushed me down and climbed on top. As she started humping she directed Jimmy
"Now do my ass"
Jimmy did it again and I couldn't believe I was watching a beautiful young girl fuck me as her b*****r rimmed her.
I came, Susan came and we collapsed.
"So Jimmy" I said. "How long have you been gay?"
"I'm not gay"
"Okay, how long have you been bi?"
"I'm not" I've never done anything until I met you. Your dick is something. I'm just attracted to it"
I looked at Susan
"As far as I know, it's true"
After that night I knew I could fuck whenever I wanted. I rarely wore anything more than shorts. If Susan was busy or not at home I would fuck Cynthia. If Jimmy was home he would watch. Sometimes Cynthia and I would watch him suck me.
If Cynthia was busy I would fuck Susan. Pure bliss
Abut once a month I would fuck Jennifer, the red head. I didn't tell Susan about her. Jennifer was a thrill because felt like I was cheating. She showed me pictures of her fiance and the two of them together. That was fun.
At the end of the summer Susan, Cynthia and Jimmy tired of barely making ends meet and they went back to their home town. I went back to college. I continued to see Jennifer.
That year I met a great girl, my current wife and I fell in love. We married just as we both graduated. I think the experience I gained that summer gave me the confidence to approach her and make her happy.
I'm now married and have two great k**s.
I continued to see Jennifer but eventually broke it off. I feared getting caught and losing mt wife.
I did have one last odd encounter due to Jennifer.
About two years after I was married she called me at work and asked me for a favor. Her current boss was female and highly successful. She also hadn't been laid for some time. Jennifer was up for a big promotion and she wanted me to take her boss to dinner.
"You're pimping me out?"
"Yes, kinda"
"It would really help me" she said
She assured me her boss was attractive
"I'll try it. If she isn't everything you say, I'll bail"

It was set up for two evenings later. We were supposed to meet at her bosses' place, go to dinner and see how the evening played out. My wide was with her mom so that wasn't an issue
I went to the swanky apartment building and she rang me into the building.
Jennifer let me in the apartment and guided me to the living room.
The entire wall was all glass and I could see the Portland skyline. Jennifer handed me a drink and I stood up to take a look.
I heard a women's voice from behind.
"Jennifer tells me I can have you for anything I want"
I turned abound and there was this 35 year old attractive women standing there. Jennifer was gone"
"My name is Elaine"
"I'm Derek"
I looked up and down. She was lean, had light brown hair that was almost turning gray. She was wearing a sheer night gown.. I could see the outline of her tits and they were healthy. Not real big but very good shape
"Well; is it true? Can I have you?"
"I guess"
"well then why don't you start by stripping?"
"I had never been directed like this, but Jennifer had give me some great moments.
I took of everything and stood back a bit.
"Wow, that dick is everything she said it would be"
Elaine approached me and dropped immediately to her knees. She examined my dick.
"I've never seen anything this big"
She licked it and examined it. She eventually took me in her mouth.
I stood there, with my legs apart, taking in the view of the city while this women sucked me off.
In no time I shot a load I thought would gag her. She kept a tight grip on my member and swallowed every drop.
Elaine got up and dropped her gown. She swill had it
Yeah she wan't a spring chicken but she had spent a lot of time in the gym.
She also spent a boat load of money at the spa getting everything waxed and buffed.
Her naked pussy looked like a teens and reminded me of Susan.
I started growing again.
Elaine pulled me on the carpet and into her pussy.
We fucked twice, each time ending in a great orgasm.
"That was wonderful" she said. " I owe Jennifer"

About two weeks later I received a text
"got the promo....thanks"

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Categories: First TimeTabooVoyeur
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