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:

Ski Trip

My boyfriend invited me to join him and his friends on their annual ski trip. I told him yes, but I have never been skiing. The weekend arrives and we make the three hour trip to the house they rent. When we arrived, I immediately was uncomfortable. It was me and eight other men. I never asked and I was never told the details. I would be here for four days.

It was quickly apparent that I was here for reasons other than skiing. They wanted someone to cook and clean. Later that night I was to hostess or entertain while they played poker.

In a return trip from the kitchen, my boyfriend said he lost a hand that he used me as collateral. I pretended to play dumb but finally said what do I owe to who? I was told I had to sit on Darren’s lap for the next hand. He would be able to touch me. That did not seem that bad. (Later they would explain that once I was used at collateral the first time, I would be in play for the rest of the night.)

I rode the lap of six men during the game. I also was used as collateral for higher bets too. I did not want to do this at first, but a little (help) helped my courage. The first was head for a guy named Anson. He came in a few minutes. The other guy was Kevin. He made me make myself cum in front of everyone while sitting on the couch. I came the first time and they told me to keep going. I did, two more times. At this point all I wanted was to be fucked so I just asked for it. They dragged me to the floor and one by one they fucked me.

I did not leave the house for the entire weekend. In fact, I never fully got dressed. I was basically a toy for them to play with when they were not skiing. I cannot wait for the next ski trip!

The Number Of Unfaithful Women Posting Their Stories Is Alarming

It’s alarming how many women are having extramarital affairs and even more alarming how many are ending up getting pregnant do to those affairs. Believe me it’s not worth the risk.
Years ago when it was more taboo for this kind of behavior I made the same mistake.
I was 23 and had been married two years when I started working for a middle age gentleman.
One evening after work he invited to have dinner. My husband was out of town working so I saw no harm preventing the need to prepare a meal for myself at home.
He was married so I had no idea he was interested in me in any way except as employee.
After that evening he began giving me more attention at the office adding duties to my job.
A couple of months later he was aware that my husband was again out of town working so he again invited me to have dinner with him.
At dinner he order wine which I never drank but not wanting to be a prude I had too much getting very tipsy.
When he made it obvious he was interested in me more than an employee I was flattered but tried to hide the fact that I found him very attractive too.
On the way back to my car he drove into a vacant parking lot. When he leaned over to kiss me I didn’t resist and quickly getting very passionate.
Without saying anything he drove to a local motel where we had intercourse for the first time. After that I would see him any opportunity we had over the next several months. I would avoid having intercourse except immediately after or before my period.
Then we had to attend an out of town conference for the company ending up sleeping together for several nights despite having separate rooms
That month I missed my period but had no way of telling for sure who’s it was except that when I calculated my fertile days it was the exact days of the conference.
Against my better judgment I admitted to my husband I had been unfaithful and couldn’t be sure who had gotten me pregnant.
He immediately filed for divorce leaving me with the options of an abortion or having the baby.
I let my boss know the odds were in his favor due to our days together so he convinced me to have the baby agreeing to give me complete support. The baby ended up as he to agreed looking exactly like him.
I never married again raising a beautiful young lady with him supporting me throughout.

Holiday Surprise

While home from college for a weekend in September I stop by a friends house to see if he’d be interested in playing golf that afternoon. His mom was home but he had gone shopping with his girlfriend.
His mom is a very attractive petite divorced blonde lady in her late 30’s or early 40’s.
We chatted for a while and I got the feeling she was flirting with me so I complimented her on how nice she looked.
To my surprise she immediately started telling me how she had always thought I was a handsome young man that any girl would be lucky to have.
I took a big chance taking her hand pulling her in and kissing her. When she didn’t resist I kissed her again which led to more passionate kissing. She had on jeans so I just ran my hand between her legs to get a reaction.
When she grabbed my hand I thought she stopping me but she took it leading me down the hallway to her bedroom.
She wasted no time unbuttoning my shirt then my jeans before telling me she was going to get more comfortable and would be right back going to the masters bedroom bath.
I took the liberty to strip down to my underwear then lying down on the bed.
She came back wearing a robe which she quickly dropped revealing her firm little petite body. I must say she knew how to use it to satisfy every bone in my body.
While I was home for Christmas break I told my mom I was meeting the lady’s son for lunch. She asked if he’d said anything to me about his mother being pregnant. I about choked on the coffee I was drinking but told her he hadn’t.
She hadn’t said a thing about using a condom so I had assumed she was on birth control.
When I went to pick up her son I purposely left my phone so I told him I’d be right back I needed to get it.
She was in the kitchen so I asked her if she had any thing to tell me. She looked at me and calmly said I had gotten her pregnant so we’d talk about it later.
I met her a couple of days later for lunch where she said she didn’t want anyone to know who had gotten her pregnant and wasn’t expecting anything from me.
I told her I would be glad to do anything for her but she said she wanted to go it by herself.

Sex Story

Been going out with my bf for about 3 or 4 years, still not living together. For a while he's been asking about my sex life before we met.

At first I played innocent, saying it was pretty normal and uneventful. He didn't buy it. He knew I was holding back. I said I lost my virginity in the back of a van in a carpark near a beach one afternoon, ain't that normal?. Yeah but what else. I said his dick was bigger than I expected and it hurt.

I told him about having oral sex with a pharmacist in the back of his shop after hours. He was engaged to be married, not to me, so he said kissing wasn't cheating so it was all good. Yes, but the lips he was kissing was downstairs not upstairs. He taught me to cock suck. He held my head and said pussy tastes a lot worse than this. ( Something I'm sure I don't believe ) . Just swallow it as soon as it comes out, you'll be fine, he said. I wanted to experience it, if only because he'd made me cum with his tongue. He ejaculated, I swallowed. I felt a momentary panic but it went down easily, there wasn't much taste . I calmed down quickly and thought, yeah that's ok .

I also shared a house between jobs for several months with two guys and fucked them both on a regular basis. They knew I was doing both of them. My bf got his dick out and started to play with it, wanting to know all about it.

By now I had a pretty shrewd idea where all this was going and demanded to know what his fantasies were . Finally he confessed. He wanted to watch me have sex with other men. ( Men ? )

I told him no. After thinking it over for a few weeks and going online to see what was on offer I said to him one night, "Look, let's join this mature swingers group, you can watch me in a quiet, party atmosphere have sex with men and have a mature lady there rub your hard on. Mature swingers ? Bf was five years older than me and I felt comfortable with older men.

It wasn't quite what he wanted, but he agreed. He listened in as I talked on the phone to the couple who ran these parties, and they seemed pleased to have us join them. I told them my bf wanted to watch. She said, what, you want to fuck several men and he only watches ? I told her that' s it exactly. They said no problem.

It was great. It was a small party in their living room and kitchen. ( There was a cost ). When you wanted to fuck you went down a passage to an annex. There was a small room first where you undressed. Women wore lingerie. There were bathrobes, towels, condoms if you wanted them, lube. Bathroom to one side.

Then you entered a dark room, mirrors on the wall, mattresses on the floor, pillows. A mirrored ball and coloured lights.

There were six couples of us party goers not counting our hosts and all wanted to fuck. They were good people. It was a stress free and friendly way to just lie back back and be fucked. My bf watched and a woman with a large body and beautiful face sucked on his dick. I had three men ( One went twice ) There was some oral.

My bf was satisfied and said this was our way forward sexually. Suits me.

Husband Encouraged Me

Since we have been married, five other men have fucked me over the past ten months. A couple of them repeatedly over several months. I am 28 and good looking with a good body. I like sex. When I meet someone I am attracted to, I let them fuck me right away. I am picky though, so it cannot be just any man. I also love seeing a man's erection because I know it will soon be in me. Every man has known I am married and that I'm just interested in recreational sex. So, no commitments. Now, before you judge me, you should know my husband asked me to fuck other guys because he gets off on knowing other men has cum in me. I tell him every detail of what I have done with another man, and it gets him really aroused. To put things in perspective, I fuck new guy about once every couple of months. My husband has watched several times and masturbates and tries to cum when the guy cums in me. I know it all sounds weird, but we both get off on it sexually. My husband fucks me really well when I come home with a story for him. I expect as we get older, we won't continue, but now we are both in our late twenties and have a lot of sexual energy.

Why Oh Why?

I’m in a happy marriage of ten years two kids, a beautiful home and loving my life. My husband is and always has been a real stud.

I know I’m the problem. I love exposing myself, flashing my bare pussy in public or giving men of all ages a look down my tops or showing side breast.

I really get off on walking by the windows of our home nude and even walking around our backyard naked.

I have never ever cheated on my husband nor wanted to. So why did I answer the door naked and then allow a UPS driver to fuck me? I have never crossed into that territory and although I feel very guilty I feel compelled to do it again.

I need help

Housewarming Shindig

I came to visit my parents for the holidays and was scheduled to leave lat week but ended up staying another week. My job is very flexible and allows me to work from just about anywhere. The recently got some new neighbors a very nice family in there late 40s with a kid that’s around 12. I leave the names out but the husband is nice a bit chubby the wife a thick dirty blond short hair nice tits and ass. Looks like she works out often and from the day I met her I flirted really hard laying it thick when we where alone talking. She seems to always like to show off her body so I always made it a point to jog in the morning and she happened to be walk and jog at the same time. She told me about the open house and I told her that I’d go. That night finally came we had text a few times exchanged numbers while walking together. Text led and flirting even got her to send me some pictures that her husband probably wouldn’t approve of. She had a few that evening and was feeling very friendly. The majority of the crowd where neighbors and the booze was flowing. Her husband was talking with others and I could see that he was also feeling the booze. At one point I went over to him and brought him a few shots to help along. By the end of the night there was only a few people left husband was almost passed out people where outside and getting ready to head out. Wifey was in the living room I had her by herself and I was sliding my hands up under her skirt and shirt. I felt on her tits slid my fingers inside her eyes barely open. I walked her into a spare bedroom leaded out closed the door and went and looked around the house. Her son spent the night at a friends house husband was now on the couch snoring loudly. I grabbed my back pack and headed to the spare room. Wifey was on her stomach. I lifted her up enough that I yanked her leggings down over her ass around her knees. She isn’t a big women maybe 120 130 lbs. I set up my phone and my camera and had my way with her rear pussy. I licked tasted her pussy and ass. Very salty not bad for a night of drinking her eyes opening and closing never saying no or stop I fucked her mouth pussy and finally ass. I made 3 deposits that night all in her mouth. I’d pull out right before I came and would stick it in her mouth and use her mouth until I finished in it. Her eyes opened when I stuck it in her butt she was awake for that one no words just grunted until i finally pulled out and finished her finished in her mouth. By the time I left she was completely naked I took lots of pics. I sent her a clip of when I was in her pussy and you can see her face and eyes open and you can hear her say it feels so good fuck it’s deep. It was a 30 second clip. I sent it to her with a text that read thanks baby for the greatest night of my life. Let’s hook up again before I leave. I didn’t hear from her until late late the next morning and asked to talk the following morning which would have been Monday. We met for coffee and she had a very odd walk probably from the vigorous ass fucking I gave her. I laughed and asked her what was wrong. She said that her butt was really sore and that she had never done that before. She said that she had never cheated and wasn’t sure what to do. I didn’t understand what she meant. She said that she is married and cheated she felt bad but thinks she really wanted to have sex with me. I told her that she was eager to and even went and checked that her husband was passed out before she came back to the spare bedroom. I left 3 days later and in those 3 days I must have fucked her a dozen times. I live 3 hours away and I have her meet me at this rest area that and hour and a half from where she and I live. Its pretty secluded and she drives an a large SUV. She is a stay at home mom that now drives a little more then an hour to let me completely fuck the day lights out of her. Went from sore ass to rough anal hair pulling ass spanking. Her husband asked her what was with all the bruises. She made up some shit that she had slipped. I absolutely love to fuck her ass. It feels amazing and I’m surprised how hard she likes it. The car smell horrible when we are done and we know crack a window open a bit. We get the occasional trucker that gets a view but besides that it’s a quiet area. I have been leaving the window down further and further. If the chance happens I may let a trucker have some fun for a little cash. I’m pretty sure she’s to the point of letting me do whatever I want to her.

I Regret What I Did And Very Confused

The week before Christmas I had to attend a business meeting in an out of state location.
I’ve been married for 14 years never ever considering being unfaithful.
The evening before the meeting for dinner I met up with an associate from another office who was also there for the meeting the next day. I hardly ever drink but at dinner we shared a bottle of wine leaving me very tipsy.
During dinner I got the feeling he was flirting with me which was flattering since he’s in his mid 20’s several years younger than me.
Our rooms were on the same floor of the hotel so when we got to my door I stopped to tell him good evening then he bent over kissing me on the cheek. The wine had me relaxed just enough that I returned his kiss.
I opened then door to my room and he followed me in.
I reminded him I was married and wasn’t interested in anything but he gently pulled me towards him kissing me on the mouth.
The next thing I knew we were on the bed kissing but I had no intentions of going any farther.
When he started to run his hand up my leg I said no we can’t do that but he quickly found what he was after at the same time rolling over between my legs. I kept telling him we needed to stop .
I had no idea he had been able to get himself out until he pulled his fingers out then put it in me.
I let him know I could get pregnant because I wasn’t on birth control then just enjoyed some incredible sex with him.
I now regret letting it happen because I am pregnant but can’t be 100 percent sure by who. The odds are in his favor since my husband always uses a condom.
I could confess but it would destroy my marriage.

I Never Knew I Could Get Lost In A Single Room.

Another Friday afternoon, work has now ended. It's now time to go and face another long and boring weekend with nothing to do than to eat, sleep and tidy the one bedroom i now occupied. I have been routinely living this way for more than a year now in a overseas job that i took on. Living so far away from home can leave you lonely which is my new situation.

Now after a year of working my new job i still have no real friends except for some guy that i met at the hotel where i work. He was a visitor from room 23D. He's always by himself, he speaks little to no words, and he is one of the big spender type. I am one of the Hotel supervisor who from time to time being called upon by visitors with complains. Now let me call him room 23D for the sake of keeping his real name anonymous. He called and ask for a supervisor after feeling disgruntled at the treatment of our room-service attendance. I went and rectified what needs to and he was more than satisfied.

When it was time for him to leave he caught up with me and gave me an envelop that contains (US$1,000) for a tip and a thank you note. Now that left my eyes wide opened. It didn't slip my gaze also when i noticed one of the US$100 note had a phone number written boldly on it so it won't be missed and what looks like his name written also.
I then said to myself "i guess this is an invitation".

I called him on the eve of the following weekend just to see what is it that he's up to. I then realized he's the owner of a 'swingers club' that is located some 3 hours from where i'm staying. It is a lovely place with a nice bar, a nice gaming lounge and a glamorous 'red room' for special invited guess.

I have never been to anything like this in my entire life but i ended up there at the invitation of room23D. I ate some of the finest food and drank some of the finest drinks including alcohols that spins my head after a few drink and within a couple of hours i'm now fully naked in the 'red-room'. I remember being taken there by room 23D and we got naked and joining a host of others in that large bed. The sheer excitement that comes from being there was too much for me. I just lay there and could do nothing more than just let myself go. I've been spooned one after the other by god knows who, with cocks going in and out of me. I literally felt all my body fluid being drained from me.

I felt many different size cocks where some have made me tremble. I was also placed in a position where i'm being fed by a breast nipple, a large cock in my pussy and a tongue licking my clit all at once. There were a time when i noticed the scent of a woman's juice feeding my mouth while i licked with passion. They did it all to me while i got lost in ecstasy. I literally got fuck from men and women for more than 2 hours and i only knew the face of room 23D and no one else.

Football Game

My best friend (Gabby) and I went to DFW for the recent college football game. Our team lost, but enough about football.

After the game, we got invited to an after party by a group of guys behind us at the game. They were much younger than us but we decided to go.

A few hours later, I leave to go to the bathroom and get a drink in the kitchen. I come back from the bathroom and Gabby is on the couch getting fucked doggie style. The guys are around her encouraging the guy in her pussy to fuck her harder and she is loving it. I yell to her and she says come on Kel, love a little. She ushers me to sit in front of her. I walk over and she says I want to ate you, so take off your pants.

By the end of the night, six different boys had fucked us. We left there in an Uber and all I could think was I am sure there are pictures of this.

I am home now and my body (specifically) my pussy feels beaten up. I am ashamed. Shit, I could even get pregnant. Ladies, be careful what you do when letting off a little steam.