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:

Thanks Goodness For Plan B

Over Thanksgiving a friend and I went to the Cayman Islands for holiday. She 39 and been divorced for about four years and I’m 43 divorced since last July.
We were staying at a nice condo on Seven Mile Beach which was fantastic and close to the nightlife and amenities of George Town.
A couple of days after we had gotten there we went for dinner to a nightclub where
there were lots of locals along with other tourists.
While there a couple of very nice local younger black guys chatted with us giving us some tips on things to do around the area.
Later that evening after we returned we were talking when my friend asked if I had ever been with a black guy. I told her I hadn’t so said she had dated some and it was very different and enjoyable.
A night or two later we were at another nightspot when the same two guys showed up. They immediately joined us with some great conversation during which we learned they were in their mid 20’s.
After a while my friend asked if I needed to go to the restroom which we did. Once there she asked what I thought about hooking up with the guys. I quickly reminded her I wasn’t on birth control to which she replied that was what condoms were for.
We returned to our table having a few more drinks so when they asked if we’d like to try another club my friend answered sure.
We were at the other spot a short time when she whispered asking if I was ok to invite them back to our condo. I was a little apprehensive about it but then I agreed
Once back at the condo it didn’t take long for things to move along so each of us went to our bedrooms.
To say I wasn’t nervous would be an understatement. I told the guy I was with that I was going to get comfortable then went to the bathroom putting a long tee shirt over just my panties
When I returned he lying on the bed with only his undershorts on giving me a view of what I was about to get.
After a few casual kisses while he played with my tits he moved down starting some amazing foreplay.which in no time had me very horny.
When he stop to take his undershorts and my my panties off I quickly told him he needed to use a condon. Without saying anything he went down giving me oral sex until I was so aroused that when he put his penis in me saying I really didn’t want a condom I was more than willing.
I had never had a penis go that deep in me so I immediately had an orgasm like none I’d ever had. He said … like that black c__k huh…and I replied yesssss.
He had a slow rhythm which again brought me to an amazing climax as I could feel him throbbing inside me the giving me the works.
Later after the guys had left I told my friend the first thing we needed to do the next morning was get me the morning after pill because we hadn’t used a condom.
She got a thrill telling me she knew I would enjoy my first black but didn’t think I’d go that far.
He had given me plenty to be concerned about so the pill was a real necessity.

I Am So Ashamed But At The Same Time Im So Wet.

I got married over 2 years now to a wonderful husband who meant the world to me.
My life felt perfect when i got married and my love were shown at every level including giving up my body sexually in ways that undermined my true character.

And here i am today to make what i called a very shameful confession.

Now my shameful struggles begin with my 17yo neighbor who i'm always wetting myself over. I use to deny my feelings for this young man until i start having sleepless nights thinking about him for uncontrollable reasons. Now to add to my shame i made a very bad move when i confessed to him how i felt about him.
I could feel him gaining control thereafter.. And of course he started calling me by my first name. And because he now gets a sense of how weak i am getting toward him he started taking many immature chances.

Last summer i went to a party by his house by invitation. My husband was still at work so i went alone. This young man saw me way behind a group of people when the toast and the singing of the birthday song was taking place... He ran his hand under my skirt and he forced his finger deep into my pussy. I almost fainted the way i was frightened. He tried to do it again that same night but i make every effort to stay with the crowd.

The very latest was during the Christmas period when he came over by my house when he knew i were alone and he almost fuck me. He got me weakened and were about to strike but i got rescued by the call of his mother even though i was surrendering right at that moment.

Part of me want to fuck this youngster but another part is saying don't do it. He's already in my heart and there's no question about it. What i also know is that if he ever catches me again like the way he did in my kitchen my wet pussy will surely betray me.

Hotwife

My husband and I have been married since 1994. We have been in the lifestyle since we got married. For the past 10 years, I have been a hotwife. I am free to sleep with anyone I want. My husband believes that I should always be fulfilled and happy. This isn’t normal but it isn’t unheard of either.

Now for my confession:

Prior to getting married, I had 45 sexual partners

In the first part of our married life prior to the last 10 years, I have had over 300 sexual partners

In the last 10 years (as a hotwife), I have had over 200 sexual partners. This part of my sexual life spans 5 continents, 3 oceans, 5 gulfs, at least 20 planes, hundreds of front and back seat romps and many demographically unique men. It also includes 4 women.

I am thankful for the ability to have sexual variation while having a loving relationship with my husband.

If Only They Knew

My wife's brother is engaged to a girl I used to fuck in high school and my early 20s. Not only that, I had a threesome with her and her older sister in the back of their family Suburban junior year. After he introduced us and we obviously knew each other my wife asked "how well" did I know her. I lied and said we used to hang out in the same friend group. I suppose they'll never know I came in every hole on that women's body for the better part of 5 years. I was her first anal, her first cum swallow, and the reason she got on birth control in high school. She was my also my first anal, first girl to swallow my cum, and only threesome.

I Did It For Him

In the recent days, someone posted a confession about her playing with her husband's friend and now she is hooked. This happened to me as well. It happened in November.

We had gone out for some drinks. The boys kept touching me and telling they both were going to fuck me later that night. I didn’t fully play along, but I never really stopped it either. They pick up the tab and we head home in the ride-share. I was in the middle and they both pounced on me. I was like a piece a meat, like prey. They had no regard for the driver. I sucked both in the car.

We got home and they fucked me in every position we could contemplate. But when the friend scissor fucked me on the side of the bed, he made my pussy squirt…rather gush like a geyser.

My confession is this: the friend meets met at my work almost every day. I sneak him into a private room and he fucks me until we both cum. I spend the rest of the day with his cum dripping out of my pussy. I crave his cock but it really is how he uses on me.

First Time Three Some

I have a friend who I have not seen in about 20 years or so. Well one day he decided to come visit for a weekend. It was a nice summer weekend . So I made the suggestion that we all go camping for the weekend. Everyone agreed . But I said we have a problem we only have one small tent . My friend said you two can take the tent and I will sleep in my van . I then said okay lets get ready and go. We arrived to our destanation and set up camp. We then had a cookout and towards the evening . Started to drink my wife does not drink but decided to have a few we smoked some weed and started partying . After about an hour in our little party . my wife said she was board and wanted to play truth or dare . We all agreed . We let her go first and so she ask my friend truth or dare of course he picked dare. so she dared him to take off his shirt . So he did now it was his turn so he asked her truth or dare. She suprisingly said dare. i dare you to get completely naked and dance around the fire. She just looked at me and I said its up too you . She then said ok now shes about 5 foot 4 and has 38dds and always keeps a smooth shaved pussy hazel eye and long brown hair as she is danceing around the fire butt naked . i said why dont we have a three some . At first she said no way . But then said okay just onece . When ended up fucking her in every hole she had . we both came so deep inside if her smooth shaved pussy and her nice tight ass hole was deffaintly sore. The next morning she woke up and said why is my pussy and ass so sore I then told her what happened She was a bit embarassed . exspecally after we showed her the video we made

Noughty Wife

My wife has admitted that she has been sharing photos and videos with another man
He has also offered no strings sex with her
I have found this a turn on

Why Did I Agree

My husband, his friend and I had a little too much fun in the hot tub on NYE. After encouraging me to ‘just use your hand’ on his friend, the fun moved inside the house and he fun me like he was the devil. It went from my hand, to my mouth, to his tongue eating me to his dick fucking me in about fifteen minutes. He fucked me on the couch, basically folding me in half and jack hammering my pussy into submission. He just kept hammering me. I am screaming like crazy, cumming like crazy and then this pops out of my mouth - cum inside of me. I looked at my husband and he just shook his head. His friend knew I wanted it so he did not pull out when he came. I cannot get pregnant, but I crave his friend now.

Peeping Tom

Two months ago I after reading a romance novel, laid on my bed and masturbated. I had completely forgotten that my son’s friend Tom, was coming to trim our trees. I was totally engrossed with my fingering when I caught him at my bedroom window getting a real eye full. I should have been embarrassed, I should have covered up, shut the dr**es, stop my fingering but I didn’t. I got a buzzing go through my body to my loins. I pretended I didn’t see him and even went as far as positioning myself in such a way where he got an exceptional view of my wet and open pussy. The intensity of my orgasm was incredible. I laid there caressing my breasts when I heard a knock on my front door. I knew it was him and put on my satin cover, short that showed plenty of leg. When I answered the door nipples erect, he asked if he could fill his water thermos. I took it from him and as I filled it for him, he came up from behind and placed his hands on my bare ass. I wasn’t expecting that and when I turned around he had my robe opened and kissed me. We took it into my bedroom and fucked. He’s been over many times since.

Going Down The Rabbit Hole

I am watching the football game the other day and one of my female friends texts me. She asks if I want to go for a run at the park. It seemed like an odd request but I went along. When I got there she seemed a little off. We go for our run and return to the parking lot.

As we approach our cars she says she needs to talk to me about something. I said sure and we hopped into her car. I asked her what was up and she tells me she has a crush on someone that she just cannot shake. After some talk, she blurts out ‘my crush is you!’

Speechless and confused, all I could muster was a head bob. She explained that my physique made her uncontrollably horny. It started over three years ago. I was still speechless. She was worried this would ruin our friendship but she had to get it off of her chest. We talked for about an hour and we went our separate ways.

On Monday at work, I saw her at least five times. All I could do was think ‘she thinks I am hot!’ She appears to be as straight as I know I am, but there is a twinge on ‘hmmm, should I go for it?’

Tuesday, same thing. Wednesday comes and she asks me if I have plans for dinner on Friday. Without thinking I answered no. She quickly asked if I wanted to meet somewhere (think about it). She walked away. I was speechless. If I go to dinner with her, is this a date?

Thursday morning she says hi and asks about dinner. I pulled her into the warehouse and said ‘is this a date or just dinner?’ Both - she answered. Again, speechless for a moment, I finally answered yes to the offer. At this point I am a fish on dry land and way out of my league. Thursday and Friday were filled with smiles and (probably) some innocent sexual banter.

Friday night arrives and we go to dinner. I am first and I wait for her in my car. She gets out of her car, starts walking to the door and waves to me. My mind went blank as this total fucking goddess in a strapped yellow sundress ushers me into the restaurant. I am in shorts and a low cut blouse and looking good, but fuck…she was a different level. Dinner went extremely well.

I told her I have never done anything like this. She told me she would be gentle and would help me along. We kissed by my car. Well, we kissed a lot by my car. We decided to go back to my house.

As we got there, I could feel the moisture between my legs. My loins wanted this. They wanted her. We barely made it to the couch. We were naked in 10 minutes. I ate pussy for the first time. She ate me too. We found my toys and a cucumber from the fridge and well, you can imagine.

Five days later, I feel like a teenager after having my first kiss. We are planning on going to dinner on Thursday night. I know we will fuck again and I cannot wait.