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13
Anonymous
@confessions
21 Aug 2014 10:14AM
• 10,364 views • 0 attachments
[ − ] thread [ 9 replies ]

I hate traveling for work. What I do can be done remotely. I'm the guy relaxing at the coffee shop, or the library, sitting in the mall, anywhere I have a decent wifi connection and I'm good. On rare occasions I have to travel onsite and it sucks. This particular time was a favor for a friend. He had too much on his plate to do the job so it fell to me. Kiss the wife, hug the kids, off I go to San Diego.

The whole flight I kept starring at the letterhead on the proposal. I could swear I knew the logo, knew the name of the firm, but couldn't place it. Even when I made it to SD I couldn't quite figure out how I knew that firm. Hotel didn't do early checkin, no big deal it's a roller an a backpack I can manage. I debated about renting a car an then just hailed a cab. The firm was massive, huge lobby, hot receptionist. She took my name and told me it'd be a moment.

It wasn't until I heard the click of the heels, the gasp, and the soft voice that it clicked and I knew why the name was familiar. Standing behind me was my ex from high school. Yay awkward professional environment. She found out that morning that I'd be the one handling the job. Her boss assigned her as my babysitter while I was here. Jane didn't think it was funny, her boss probably did. Jane offered a tour of the place. I asked where I could leave my bags and the receptionist stashed them for me. I kept pace so I wouldn't stare at Jane's ass. She'd grown from the high school girl into a beautiful woman. I noticed the ring, lucky guy. She rattled off about this office or that person and I just nodded and kept going. I was here to fix the system, everything else was a distraction.

After the tour I offered to buy Jane lunch. I admitted I'd taken a cab and that I hadn't checked in yet. Just to make it overly awkward I threw in "not a date" and the smile on her face said I'd hit my mark. I was fine with taking a cab but she offered to drive. We picked up the bags and headed to some Thai place. Lunch was great. Conversation was all business until that ran out. Then things went personal. I was married, I had kids. She was married, had a little girl. We stayed away from the "since high school" cliche. I think both of us wanted to avoid talking about that part. Eventually I picked up the check. Again I offered to get a cab so as not to inconvenience her. She insisted on dropping me off at the hotel.

It was in the hotel parking lot where I sensed something was wrong. Instead of just dropping me off she parked on the side. She seemed distracted and suddenly started sobbing. She'd caught her husband Brad cheating 2 weeks ago. They were not separated. Her daughter was up with her parents for the summer and she really didn't want to go home to an empty house. I was the shoulder to cry on and I let her sob it out. I offered dinner plans and asked if she wanted to share the room. Room was already booked. She smiled and asked if I'd rather stay at her house. I started to talk about the cancellation policy and she laughed. The firm did a lot of business with this hotel, she could fix it with a single call. Hearing her laugh made me feel better. I hadn't realized we were holding hands, but I did notice her hand on my thigh. She rubbed a little bit and smiled. I didn't fight it and pretty soon my pants were unzipped.

She had her phone in one hand and my cock in her other hand. I could hear the lady's standard hotel greeting. Jane rattled off her friend's name and the lady said it'd be a moment. Jane smiled and started sucking. When her friend came on the line she popped off and started jerking me hard. She told her friend she needed to cancel the room. When the friend started talking she popped back on. 20 minutes of off and on and me having to be as quiet as possible. Once Jane hung up she worked her magic. She knew how close I was, and she didn't care. It felt amazing to drain my balls in her mouth. She stayed on a few moments longer and sucked me dry, swallowing every last drop. I tried not to laugh when she said "hope you wife doesn't mind I borrowed you".

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3
Anonymous
@confessions
23 May 2025 2:35AM
• 425 views • 0 attachments
[ − ] thread [ 2 replies ]

Have you ever had a woman you wanted and lusted over for a long time, and then, when it finally happened, it was all you imagined it would be, only to be disappointed at the end?

We both knew Maya back in hs. She was by far the pretties girl in the entire school, but she wasn't popular, no, she was one of the nerdy girls, yet, the way she dressed, so closed and unrevealing, nor the way she acted, all shy and introverted, couldn't fool guys to look over her hotness.

She was our friend, and we both lusted over her. I tried something, she rejected me, like she rejected everyone - no one could touch her.

Now, this all happened in my home town, and as I went to college, she stayed, with him, my best friend. First Christmas I came back home from college, they already became an item, but we kept contact, all the way through college. Every time I visited, she evolved more and more, into a mesmerizing woman, being with him gave her confidence, both socially, and about the way she dressed, behaved.

I got married to a girl I met in college, in the city, after graduation, and they started living together, back home.

Twenty something years have passed. I got divorced in the mean time, and bought a little condo back home, for vacation, and started spending more time there. We lost touch over the years, but when I met him, and asked him about her, he confessed they broke up years ago. Then I bumped into her...

Saying that a 44 year old is stunning, always has to be taken with a bit of salt, but man, she was. I had no time to waste, texting have started, coffee dates, dinners... After one, she agreed to come back to my condo. When I kissed her, she kissed me back, and then surprised me, by going down on her knees, by herself, moments after, and unbuttoning my pants. When she took it in her mouth, I couldn't believe it. This was a woman, who I have been obsessed with for over two decades. I jerked off to the thought of her, thousands of times, and there she was.

It was wonderful, sensual, romantic. She came, while on top of me, tweeting like a little bird. Then I got to be on top, and when I was about to nut, I pulled out, but my excitement got the better of me, so instead of shooting for her belly, I unloaded all over her bald, perfect pussy.

"You didn't have to,"she commented,"there is no worries there".

That night, I learned that he left her, because she couldn't have kids. I also learned, that she is absolutely still and forever in love with him, and I decided, that that plot, is not healthy for me.

I did buckle, two more times, we spent two more nights together, before I packed my shit and got out of there, not to come back for another two years. She may be my perfect woman, but I am not her perfect man, and that would come back to bite me in the ass, sooner or later.

And that is my, said, love story.

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5
Anonymous
@confessions
22 Apr 2014 10:56PM
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I live alone with my cat and I get up early in the day any head to school(college),recently my neighbors have been fighting a bit to where you can hear them. I live in an area where the apartments are close together. I get home around 11am and at take a nap,I wake up to a knock at my door,it's my neighbors daughter(18 or 19 which ever) she goes to one of the high schools around the area,she's about 5'2 and a very very nice body,her ass is an 8 but her tits are way past a 10. She had came over to see if she could stay the night cause if her parents fighting,my place is just beside them and I've talked to them a few times and played with their daughter a few times with the other kids around,mainly just riding bikes,swimming or playing basketball. I said should could stay till it gets dark and go home,she's been over a couple of times and enjoyed playing with my cat,I would ask her to watch my place while I was out longer than I thought I'd be,I let her in she knew where everything was so I told I was going back to taking a nap and to come get me if she going home. I slept very well that when I woke up it was 8pm I had missed my whole day,I walked down stairs and she was cooking dinner. She said her parents left to go to a movie and to stay here, I didn't mind it but I wished they had asked if it was ok,so I let her stay and she finished cooking. We finished the food she made and just sat around watching tv,she must've went home to change cause she was wearing sweat pants and a sweater when she came over,now she's in short shorts and small black T-shirt. We talked for a bit about how she was doing in school and all that stuff,I soon notice she kept getting closer to me,she got close enough fore to notice she's not wearing a bra. My cat jumped into my lap and laid there she starts to pet my cat and starts talking about her relationship with her bf,now I got bored but heard she hasn't had sex with him but only gives him a bj when they're alone,I start to get a hard on and I think that's what she was going for cause her hand was petting closely to my crotch than my cat. I tried to play it off and soon she had her hand on my crotch. "Would you like to know how good my hand feel?" She said in a very seductive way,I nodded and she unbuttoned and unzipped my pants. She starts to stroke my cock,her hands felt so soft,I saw her nipples get hard under her shirt and she caught me staring at them and took her shirt and soon got on her knee infront of me and put my cock between them. "Do you like my tits? They are so big everyone stares at them in school." Omg her tits felt so good,the softness and the warmth of them made me cum on them. I was still hard,mainly cause I haven't jerked off in 3 days so I was backed up. She stood up and turned around then slowly pulled her shirts down to show a purple thing with a heart shaped opening in the back of it. We started to fuck on my couch her tits kept bouncing up and down,I suck on them as we fucked her got a bit louder,about 25-40mins of messing around she decides to go home and leaves her thong. The next day after I get home I got a picture sent to me of her tits,and a text that said "You should come over here one day,I'm always home alone."

I go over a few times a week while her parents go out,she loves to mess around on their bed.

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-4
Anonymous
@confessions
03 Mar 2013 12:45PM
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This is an absolutely true confession. It happened last Sunday.

My best friend since high school is married to an absolute beauty, whom I've also known since shortly after high school. I've lusted after her for ages: big, beautiful tits, long dark hair, very sexual woman, too (I know, I lived with them as a roommate for years and jerked off many times to her body and the sounds of her getting nailed in the next room.). Not only have I lusted after her, I've lusted after her mother, three of her aunts and her cousin. At times I've jerked off while fantasizing that all of them were my incestuous little band of sex slaves in collars and fucking each other and me.

I never have and never would make a move on her but I have always lusted after her. She has two kids with my best friend now and still has a slamming body.

Anyway, last Sunday I was over at their house helping him put in a new bathroom and the two of them had to go to Home Depot to pick up some stuff and they asked if I would stay and watch their sons. No problem. I've known them all their lives.

While they were gone their sons were downstairs on the Wii and I was upstairs and I was consumed with the notion to go through her underwear drawer. I have done it on other occasions over the years, but not in a long time. So, while the boys were downstairs I went into their bedroom and opened her underwear drawer, picking out a nice pair of leopard skin panties. Then I went to the laundry hamper and got a pair of her used panties and took them both into the bathroom. I sniffed, licked, and rubbed the used panties all over my face while I jerked off.

I flipped the clean, leopard skin panties inside out and held them out before me. It's important to note that I hadn't cum in many days (probably five or six) before this. When I came, there was a LOAD of cum. I mean a fucking LOAD, all over the crotch of her panties. My knees were shaking. I splattered my cum all over the inside crotch area of her clean panties, which I then folded back up exactly the way she does it and put them back in the drawer, second from the bottom in the pile of her sexy underwear (The dirty underwear I sniffed, licked and rubbed on my face was more plain, everyday stuff, black but high cut.).

I then put the dirty underwear back and continued throughout the day. I went down and played Wii with the boys and had a snack, then they came back and I acted like nothing had happened out of the ordinary (or course.).

I really loved doing it. The next time she wears those panties she'll have my cum between her legs, against her pussy lips, where I always felt it belonged.

I'd do it every day if I could but that opportunity rarely comes up. When they had an apartment years ago I would occasionally stay with them and while they were out I would go through her panties, mainly the dirty ones, and sniff and lick then and rub them all over my face while jerking off, but I never came in her panties before.

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