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Caught At The Window With My Friend

Posted by: Age: 16 Posted on: 9 comments
18 likes 24 views Category: Masturbation Male-Male Tags: Watching, jerking, mutual masturbation, neighbor, friend, caught, stranger, blow job

So it's been almost a year now of watching the neighbors have sex or just watching Michelle get undressed. I'd guess once a month. My best friend and I are able to catch them or her and jerk together by the window.  Well one Saturday night,  things went south. 


My parents were going out of town for an overnight and I was staying home to watch the house and dogs. I have Eric come over so I won't be totally alone.  We chill during the day and go grab Taco Bell for dinner.  We get done eating,  it's like 8 pm, and I take the dogs out. I notice the neighbors' car isn't home, so they must be out.  I go in and tell him,  so we leave the door open to hopefully she the headlights when they pull in.  After about an hour, sure enough,  I'm in the bathroom,  Eric says they just got home. 

 

We get in our normal black outfits and head out back. The bedroom light turns on, so we get close. We can see them walk in,  Michelle is stumbling and laughing. It looks like to us they had been drinking,  and she had too much.  I whisper to Eric, I hope they still have sex. They start making out, her husband is groping her breasts. As they make out, her husband is slowly undressing her.  At one point he has her blouse and bra off sucking on her nipples. That must have done it for Eric, he drops his pants.  I'm hard but waiting see to more.  Her husband then gets her pants off, and lowers her panties. This must have been a special night, for the past year Michelle has had a neatly trimmed pussy. Tonight she was fully shaved, and she was horny,  you could see her clit showing while she was standing there.  I couldn't wait,  I now drop my pants and start jerking.  Her husband starts fingering her,  she stands there, legs spread moaning as he pounds her pussy with his fingers.  

 

 

Then she bends down and starts taking his pants off. He is rock hard, she pushes him down and climbs on him.  They are 69, her ass facing us.  I've never seen her asshole or pussy so close to the window.  I was so turned on.  At some point I here a noise and look to the road,  there is a women standing next to me by the large bush we were behind.  I jump, and say what are you doing.  Not loud tho.  She smiles and says I'm wondering the same.  I pull my pants up immediately, Eric stops and does the same.  She asks what we were doing,  I say nothing.  She then says,  oh that was more then nothing.  I say now what then.  We walk away from the window to NY side yard.  She says, well what you were doing you could get in a lot of trouble for.  My heart is pounding out of my throat. I respond with, I'm sorry.  What she says next,  still shocks me to this day.  She says we'll I could report it, or the two of you could continue doing what we were doing but she was going to watch.  I say what do you mean.  She says I know you both were jerking off. Then she says are you two gay. I respond and say no,  we're horny boys,  we were watching the neighbors have sex.  She says even better, if you don't want trouble, you're going to let me watch.  

 

 

She then explains that she is a widow. Her husband passed 8 years ago, and they were very sexual. She said she was 60 now and hadn't had sex or gotten the urge since he died. She said I was walking,  which she did late at night because it's peaceful and she happened to notice us doing something and came to look.  Then she says, "Make up your minds." Immediately, Eric drops his pants,  his dick is still hard, and he starts jerking. She says, "I like your decision."She looks at me and says, "Well..." I drop my pants, not hard anymore, so I say, I have to warn up.  She says OK, I'll watch him.  Not sure if it was nerves or what but I was having trouble getting hard.  Eric seemed to be fine,  after minutes he says I'm gonna cum.  She says, cum for mommy then,  Eric explodes, shooting his cum all over the ground in front of her.  She licks her lips and says, nothing better then hot cum. After he's done,  he says can I go.  She says go clean up,  your good with me. He pulls his pants up and runs inside. 

 

 

She turns towards me and says, what's wrong,  still warming up.  I say maybe it's my nerves.  She says, well you were watching the neighbors right?  I say yes.  She goes,  well I'm old and may not be helpful but here. She was wearing a nightgown like outfit. Looked like a oversized shirt.  She pulls it up,  revealing her hairy pussy and huge kinda saggy breasts. Her nipples pointed down but were hard, there was no areolas, they were skinned colored. I immediately start getting harder.  She notices and says, wow my saggy breasts and untrimmed pussy is helping. I say, you are sexy,  even with your age.  She smiles and says, you don't have to flatter me.  I'm enjoying myself. At this point, we're at most 5 feet apart in my backyard. She takes a couple of steps towards me and says your cock is nicer then your friends. I thank her.  She then says do you mind.  I stop jerking and say mind what. She gets down on her knees right in front of me.  She grabs my hard cock and says, let me take over, I say ok. She slowly starts jerking my cock, pulling my skin back and forth. She says, I've only ever been with my husband and he was cut. I've never played with foreskin.  I say ok... She then pulls all my skin forward and puts me in her mouth. Her tongue is rubbing my foreskin, it felt so good.  At this point the most I'd done was finger a girl and she jerked me off.  It felt so good,  I moaned quietly. She said, am I your first,  I say yes.  She smiles and says, I'll take good care of you.  She then proceeds to jerk and suck at the same time,  it felt amazing. It didn't take long and I'm close.  I say to her,  I'm really close.  She pull off my cock just long enough to say, then cum. She went right back at it, 2 strokes in I let out a deep breath and cum into her mouth.  She stops jerking with her hands and just uses her mouth.  Teeth on my cock sucking hard, I'm had a week worth and she drained all of it in her mouth.  By the end I grab the back of her head and thrust the ending out. She then pulls back and says, swallowed every drip sweet. 

 

 

She stand up and says, go clean up,  I'm going home to masturbate. She said this would be her first orgasm in 8 years.  Oddly I say, thank you.  She smiled and walked away.  I pull my shorts up and head into the house.  Eric is cleaning the floor up.  I ask him what happened.  He said he cleaned up and I wasn't in the house so he went to the window to make sure I was ok. He said he saw her naked body and got hard so he started jerking again.  He said then I saw her giving you a bj and I came all over the floor.  We talked about it so night.  What a crazy night yet again.  My first bj from a widow who caught me peeping. Crazy......

 

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