Derwood_lolly

Derwood_lolly Avatar
Gender: Straight Male
Age: 40
Relationship Status : With someone
Profile Visits : 331
Number of Comments : 55
Number of Confessions : 0

Derwood_lolly's Favorite Confessions:

Taken

I got married when I was 25. It didn’t turn out as good as I had hoped. I was divorced at 30. No kids. No house. Good nursing job.

At 31, I decided to reboot my life. I moved to a warmer climate after finding another good nursing job. I have since bought a condo in a nice suburb of a large city.

With all of that in place, I started to allow myself to find partners to meet my sexual needs. I wasn’t open to a relationship per se; just sex and fun. I went on a ton of first dates. Some were good and some were not.

I met one guy from another department at work and we had a really cool first date. We went axe throwing. We had dinner. We spent some time walking on the pier. The second date was more intimate. The third was our first full sex.

The fourth date is where my confession comes from. We are at his house playing on the couch when his friend calls him. He answers and says sure, come over whenever. It struck me as odd, but whatever. We take the play into the kitchen (that is a story for another day) and he ends up fucking me as I was bent over the table. He really pounded me that night. He was vocal too - calling me naughty names, spanking me and pulling my hair. I took his lead and let myself go - asking for more, moaning loudly, encouraging him to fuck me good.

Out of the blue, he stops fucking me. Like an angry cat, I whipped my head around and growled at him to keep fucking me. He teased my pussy with his head. I growled again….give it to me. Then there is a knock on the front door. He yells come in Jackson. At that point, he pulls my hair, lifting my tits off the table and rams his dick into my pussy. All I could do was yell fuck yes, fuck yes. His friend stood there watching him fuck the shit out of me until he asks if he wants a turn. He pulls my hair again and says do you want his dick too? His friend answers sure, I will take a turn, drops his pants and waits for my answer. In a completely shameful display of submission, I answered yes, I want him too. He let go of my hair. I tried to bury my embarrassed face into the table, but they were not having it. His friend got hard and rammed himself balls deep inside of me. He filled all of me as my date pinched and pulled at my nipples and spanked my ass. They used me hard on the table for about 15 minutes. They then took me to the bedroom and completely took me. I am a good girl and nothing like this has ever happened to me. I did a spit roast for the first time and I thought I died and went to heaven. When they finally had enough of me, I had cum eight times. My pussy ached. My lower stomach was sore. I had swallowed three loads and I wore two others. I had gone to a place I had never gone.

They wanted to do this again, but I could not until my body had recovered. We all meet once a week to play.

My Secret Life And My Secret Past Revealed My Boss Fucks Me Now

My mother and grandmother are both very tall. I inherited that as well, I topped out at five eleven. In a world where almost all women are shorter being so tall made me stand out and it made me want to hide. I got called a giraffe by the other students in school.

One day after high school, before I went to college, I walked out of a restaurant with a friend. She is also tall, and we both played volleyball. This man walked up to us and told us he was doing a shoot for an advertisement of the restaurant, and we were perfect, and if we would let him shoot some pictures with us to use in the advertisement. We would give consent.

The pictures were good, two high school girls at the door, with the restaurant sign above, and the downtown skyline behind that. He told me I had the look that photographers looked for with models, and being tall helped, short girls didn't make good shoots. He had me stand still, pull my shoulders back, 'yes get that rack going girl' and some of that. He gave me the name of a photographer in town and I should look him up, he gave me his name to use when I called.

I didn't call immediately, but when I did the photographer said he remembered his friend telling him about me. I went to his business, in the older part of town, in a small house. He had a small reception in front, and a studio in the next room, and the technical and developing room behind. He said he liked the feel of developing his own pictures, as opposed to digital and he showed me some wedding pictures and family pictures. If I wanted I could sign the release and he would take some pictures and see if he could market them.

In the room for the photographs, it was dark and the windows were shaded so he could control the light, he wanted me to, well undress. Nude shots is what he said sold best,. The first set were demure shots, covering my breasts, but the other ones were X rated and the more he encouraged me the lioness in me came out. Full frontal, on my back my legs held high, back side photographs, tit pictures, anything goes. He developed them and showed them to me and I got hot. Like hot enough to rub myself silly with them.

All through college I 'modeled' for him, the photographs were used for all sorts of magazines and digital sites. Names like Clara, and Cristine, and Elain were used. The more I shot the more I got hot. It was in college that I realized, like a light going off, that I liked to see naked women and rub out an orgasm or two. He had lots of girl photographs and he loaned me the ones that made feel hot.

He introduced me to a girl and said he would shoot us together, making out. Both naked, on a small bed so that the photographer can get all your parts. we kissed and made out. I liked it, kissing with her and I was soon dating her and we were making out alone without him, and kissing the forbidden fruit. The more we dated, the more we kissed and made out, the more we went down and had pussy for desert, the more she came out and introduce me to the lesbian scene in town. Gay is gay, but lesbian is lesbian and the twain shall never meet. Who gives a fuck about gay men and their problems, we had our own. I embraced the lifestyle and having a girlfriend to make out.

The lesbian scene lasted until well after I graduated and got a real job. My other life, the girls, the photographs, all that had to stay in the background. One day at work I broke a tooth. My boss took me to his dentist and said it was an emergency and I needed to be looked at right away. The dental assistant that attended to me was a lesbian I had met in the lesbian underworld. Small world, really. She has such fine tits. And she made sure that her tits got in the way as she helped the dentist do his work.

When I left, my boss was waiting in the reception, she came out and said 'sweetie you forgot your kiss' and she planted one on me in front of my boss. That's how my night life, my past, my favorite things came to light with my boss. And for him, there is nothing better than a tall naked girl leaning over the kitchen counter to fuck. I have to lay there beside him and tell him stories of lesbian women I've been with, how lesbians fuck. Details, details, and photographs too. Of me, naked, of me kissing a girl too. Then he fucks me. And that's how it's been for a while now, since he found out.

New Years Confession BJ

This past new years I was at party it’s my boyfriend when I saw one of my brothers friends growing up. I had a crush on him in my late teens and he is about 3 years older than me. I was excited to see him and chatted him up for a while since we haven’t seen each other in a couple years. Obviously everyone was drinking and partying and conversations got a little bit more and more sexual. At one point in the night I just straight up told him that when we were younger I had a crush on him. He said he knew but wouldn’t do anything about it because he was friends with my brother which I totally understood but he also added that he would have gotten a piece of me if it wasn’t for the friendship. I won’t lie that got me a little hot and bothered maybe even a little horny. He was looking at me like he would fuck me right now but we parted ways and talked to other people for a while before we came back to each other. I’m way more drunk now and my boyfriend was not around at the time and just told him that I’ve wanted to suck his dick since I was seventeen and h just smiled and took my hand. We went into the garage he pulled out his dick and I started sucking. My pussy was super wet and his cock tasted so damn good and it was a very nice size. I told him he could cum wherever he wanted and eventually unloaded and filed my mouth with his man juice. I was so happy he was happy I did t care about my boyfriend at the time and I would do it all over again. We have been texting now and will see where this goes.

His Colleague, My New Lover

My husband came home from his company Christmas party with an older male colleague a fortnight ago.
They had a drink talking about this and that, then my husband tells me out of nowhere, Mike has a really big cock.
Before I know it, Mike is stood in front of me with the biggest dick I've ever seen. My husband practically orders me to suck it, so I did.
After a few minutes I heard my husband say "That's enough". But by then both Mike and I didn't want to stop.
My husband says it again, only a little more forcefully, to which Mike tells my husband to "Shut the fuck up, you wanted this".
By this time my pussy is aching for his huge cock and I decided to see how it'd feel deep inside me.
Removing my skirt and knickers I knelt up on the sofa and Mike got behind me.
The feeling of his large length filling me was so good, so strong, I climaxed immediately.
And for the next ten minutes or so as he fucked me so deep, I orgasmed over and over again.
My husband was angry when Mike came in me and then pulled out, but he wouldn't say anything further to Mike.
When Mike left in a taxi, my husband tried to shout at me, but I reminded him it was he who brought his colleague home. And it was he who wanted me to suck Mike's dick.
In the last two weeks I've met Mike several times and we've had sex in each others cars. He wouldn't have been someone who I'd normally go for, but he's a great lover and his cock is utterly beautiful.

Spring Break Surprise

April last year my daughter talked me into going on a Spring Break trip with she and a girlfriend to Panama Beach, Fl. I was 43 at the time and they were 20 year old college juniors.

I had been divorced for almost two years and actually needed a getaway since I had not had a vacation in five years.

We had rented a nice beach front condominium so it was a very welcome chance to just relax.

My daughter had told me there would be lots of partying so I was expecting them to be out most of the time. However, a couple of evenings they had several college aged guys over to our condominium.

I had not partied in years but again it was nice to be able to just enjoy myself.

It had also been a long time since I had gotten drunk so when the college guys started giving me attention it was very flattering.

As the evening progressed they became more open about things they were interested in but I played it down not being interested.

When a couple of them got a little aggressive I resisted but to my surprise my daughter encouraged it telling me to relax and enjoy it.

When one of them started playing with my breast I felt uncomfortable but again my daughter encouraged it then I felt someone unbuttoning my shorts.

The next thing I knew they were off with my daughter telling the guys to be sure to use condoms because I wasn’t on birth control.

I was just drunk enough to enjoy letting two college guys have sex with me as my daughter chanted go mom go. I must admit it was very exciting and enjoyable but with me reminding them to make sure the condoms stayed on.

Afterwards my daughter told me she had arranged for it to happen knowing it had been a long time since I’d been intimate and would enjoy it.

As luck would have it two weeks later I got a big surprise when my period was late. Sure enough a pregnancy test confirmed I had gotten knocked up despite them using condoms.

I had no choice but to have the pregnancy aborted under the circumstances.

Very Confused

I am so confused I have no idea what to do.

I’m 36 and my older sister is 42. We are both married to our high school sweethearts.

A few weeks ago I stopped by her house after going shopping but she was out. I was standing behind their sofa in the family room looking at TV.

I’ve always considered her husband very attractive but never had any idea he looked at me in anyway except his sister-in-law.

When he came up behind me putting his arms around me for some reason I didn’t say anything then he kissed me on the neck. I still didn’t say anything because I was actually flattered by his attention.

Then I felt him raising my skirt. I called out his name in surprise but when he ran his hand between my legs I just said of my god as he quickly put his fingers in me.

The next thing I knew he bent me over the sofa back as he continued getting me extremely aroused knowing what was going to happen. He took his time once he did bringing me to an incredible climax before finishing in me.

Afterwards we talked about what had happened agreeing it couldn’t happen again but that both had enjoyed the experience.

My husband and I use condoms for birth control so when I missed my period I’m almost certain it’s not his.

If I confess what happened it would tear the family apart so I’m very confused on what I should do. I’m sure my brother-in-law will question if it’s his even though I never said anything about not being on birth control.

Just Tried My First Huge Cock

So here goes..
I got fucked by a really huge dick last night. And WOW... I loved it!
I have had plenty of sex before, but never with someone that big.

I have never been stretched like that before and GOD it felt surreal! I swear that cock touched places inside me i did not know existed.
I don't think i will be able to go back to regular sized dicks after this...

Sorry not sorry..

Hotwife, Happy Life

When my wife and I were dating, we were both going through divorces from dead bedrooms and ended up sharing every secret desire and every sexual experience we had ever had with each other. It turned out that we were both total freaks, both bisexual, and we started down a path of incredible kinkiness. We are wonderful parents and have good jobs, and she is currently pregnant, so our swinging has been a bit on hold lately. However, since we started dating, she’s fucked at least 10 guys and 3 women, including 2 guys without me present. I have hooked up with a couple of guys without her as well. We love sharing stories of our exploits and have an extensive catalog of pictures and videos of us doing absolutely filthy things with each other and other people.

It’s so fucking hot. I love her so much, and I love that she is this amazing family woman 97% of the time, and that there is this part of her that is an absolute degenerate slut just like me. I love licking cum out of her freshly fucked pussy while we are high on poppers. To all the repressed men out there, I hope you are as lucky as I have been in finding a freak just like you!

Her Odd Request

I travel a lot for work and my coworker and I missed our flight and couldn't get another until tomorrow. We went and got a hotel, rooms side by side and went and then went and ate dinner. On the walk back she asked if I'd do her an odd favor and swear to never tell anyone else. I was hesitant but said OK. She asked if I could take some adult pictures for her. I agreed, but there is something about this woman you need to understand, she is not smoking hot. Shes about 40, really tall skinny blond with strong Germanic features. Not ugly, but not a super model either. I'm a short , 5'7" stalky guy and she at least 6'1".
We got back to the hotel, she stripped bare, skinny but cute ass, small tits, big pokey nipple, trimmed blonde bush, long pussy lips. I took the pictures, spread her and positioned her as I did, and was hard as rock the entire time. After about 30-40 pictures she asked if I would jerk off and cum on her. She made it very clear she didn't want to fuck, but said if I came on her it would make better pictures. So I did, rubbed her skinny ass and wet pussy as I jacked off and blew my load on her face, in her mouth, and on her little tits. I took more pictures as she stroked my half hard cock with her giantess hands. The final picture she wanted was licking up the small amount of cum she squeezed out of my cock.
She got in the shower, I'm back in my room wondering what the hell just happened, and I have no idea what she plans to do with the pictures.

Harley Davidson

My father in law flirts with me and I flirt back but not in front of his wife or my husband. I love how he looks at me in my tight shorts or whatever I wear. He’s been helping us do a bathroom renovation and has been here every morning at 7am to get an early start. This last Monday I came into the kitchen in one of my husbands T-Shirts for a morning coffee. It was fairly shear, enough where he could make out the brown of my nipples. He came up from behind me and placed his hands under and on my bare butt cheeks. When I turned around he lifted my shirt up and off with me letting him. I just stood there nude as he dropped to his knees and began eating my pussy. I asked where Brian his son was, he said he’ll be awhile and kept eating me. My legs buckle I don’t know how many times before I finally came on his face. He then laid me on our tiny kitchen table and fucked me hard. We both knew this would happen and we both agreed it can’t happen again. I’m going to do the best I can not to let it happen. The guilt is killing me.