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:

Like Mother Like Daughter

My mother and father were in the process of splitting up before I was even born. As such, my father wasn’t in the picture for much of my life. I know this had adverse affects on my life and my upbringing but my mother and I are very close.

My mother is a curvy woman, with a large pair of boobs, long legs and a round booty ass. Basically, she is sexy as fuck. She has always dated black men. Until recently, I noticed it, but never understood why there were never white guys around.

So recently, she asked me to go on a double date with her and her boyfriend. I knew of my date, so there was no surprise when we got to the restaurant and there stood a perfectly sculpted man named Desmond. 6’2, slim, dressed very well, deep brown skin. Me, like my mother, I am 5’4, 175 lbs, olive skin color, 44DD.

Dinner went very well. Desmond was partners with Marty (my mothers boyfriend) in a drywall business. As the night proceeds, I am desperately trying to figure out how the night ends. I mean, it is going well and I would normally go home with the guy and fuck. But with my mom with me, how would I make this work?

My mom offers to head back to our house. More weirdness for me, but whatever. We get home and my mother says she and Marty are headed to the basement. The music goes on a few minutes later and a few minutes after that I hear her getting the daylights fucked out of her. I have thought I heard this over the years, but not like this. Marty was taking my mother hard.

Was it a turn on…maybe? Was it an opportunity to let myself go…certainly. So Desmond and I head to my bedroom. Within five minutes we were naked and I was on my knees sucking his cock. As much as I was busy, the sounds from the basement were clearly audible. My mother was getting her brains fucked out and she did not care that I heard it. A little while later was my turn. Desmond laid me on my back, on the edge of the bed, put on a condom, rolled my knees to my chest and inserted his cock in me. I thought he may break me open, but my c**t stretched and stretched. Then he went to work on me…just like Marty on my mother. He fucked me until I came…hard…and loud!!! I screamed!!! He let me regroup, flipped me over and began pounding on my soaked c**t doggie style. I was in heaven!!!

So last night: we all end up at our house again. This time there was no separation of spaces. This time Marty took my mother on one couch and Desmond took me on the other. As I am getting pounding into oblivion, I took glances at my mother getting the same. She looked so sexy, so hot, so naughty, but so happy. And then it hit me…she dated men who could do this to her. Boy do I love that woman!

Not Sure How I Feel!

My best friend passed fifteen months ago. It was hard and my fiancé and I spent a lot of time with her husband Tom, just making sure he was as ok as could be.
A month ago Tom suggested a night away for him and about a dozen friends with dinner as we hadn’t all been together for a while.
Tom was there to greet everyone and agreed to meet in the bar for pre dinner drinks. All the guys looked smart and I wore a black halter neck backless dress that made me feel good despite the occasion. When we walked in the bar I even did a twirl for the half dozen people there and Tom said you look great to me as he hugged me hello. We both stared and nodded because previously his wife and I would have got ready together when away so it was bittersweet.
After dinner as the group chatted Tom mentioned he had a late checkout and was going for a walk before driving home. My fiancé said he had to get back early but suggested I joined Tom for his walk and journeyed back together.
The next morning as we came back from the walk Tom slipped his hand in mine. Back at the hotel we picked up coffees and took them back to his room where I watched him pack.
Once done and as we stood he gave me a hug saying thank you for the last year. I leant back and looked at him deeply “I loved her but I love you too you know” and he nodded, smiled and said “love you too”. It wasn’t romantic but feeling so close we softly kissed each other on the lips.
“I’m in a hotel room with a sexy woman without making a pass, not exactly moving on am I “ he said. “No,” I replied and kissed him again, harder and for longer.
“It’s ok, this change’s nothing but you need to start” I moaned against his ear. He kissed me once more, my mouth opened and his tongue slid in as his hand came up between our bodies and caressed my breast.
I started to undo his trousers as he undid mine. We fell onto the bed laughing and then got back up to take our own clothes off. As he lay backdown I slid over him and kissed him, then kissed my way down his body and took his hard cock into my mouth. He was urgent and very quickly pulled my up. As he did he rolled me onto my back and moved above me. We stared into each others eyes as his cock found its way easily into me and as I pulled his head down to kiss I wrapped my legs around his waist. He wanted to go slow but he groaned and started to pound into me as imoaned. His need was real and I felt it as he got close “stay inside me please” I groaned and he did, coming hard as I felt the orgasm roll through me.
We lay there for an hour then showered. I held his hand in the car and he kissed me gently as he dropped me home.
I hope my friend understands.

My Daughter Won't Talk To Us Now

My husband and I have been together for 30 years. We've always been pretty adventurous sexually. Over the last 15 years we've been having fairly regular threesomes with another woman and also another man. They're the only 2 people we've ever shared ourselves with. We're very partial to these 2 people only. And yes, we've both explored our bi sides and like it but neither of us consider ourselves bi.
So, last week, Saturday, we were entertaining Tom, the other man. It had been a few months and I was in my personal heaven with these 2 men making it all about me. I had all the orgasms I could handle and it was their turn. So there I was on all fours, husband taking me from behind and Tom in my mouth on the couch. Tom cumming in my mouth and my husband pulls out and cumming on my ass when bam! Door opens and all we hear is WTF? Yep, our 24 year old daughter shows up unannounced and caught that sight. Her mom and dad not just having sex but with the man she's known as 'uncle Tom' for pretty much her entire life. FUCK!!!
She just closed the door and left. It's been a week now and she still won't talk to either of us.
I get it. It's probably kinda traumatic to see her mother completely naked and pretty much sperm covered but come on kid.. at least talk to us. We're parents but still human. We're 50 but not dead..

Heat Of The Moment

A few weeks ago my husband and I invited a bull to joins us for some fun. My husband is not very alpha, nor is he very endowed. Bringing the bull in relieves him of his humiliation of not satisfying me as well as gives me what I need sexually.However, this did not end up as planned.

This bull fucked the shit out of me well into the night. My husband got bored after he jerked off and went into the other room. Even after that, the bull kept on taking me. He was extremely hung and extremely good at what he was doing to me. When he told me he was ready to cum, he must have timed it where I was going to cum soon too and I blurted out just cum inside of me. He did and I thought my mind may go crazy from allowing it. He told me good girl and continued confidently fucking me. The next two cums, he did not even ask. He just said ‘time to breed this white pussy! and bam, he filled my pussy with his cum.

Here is our problem: I want more of this like nobody’s business and my husband feels humiliated that I gave up my pussy in such a cruel way. In the heat of the moment, my pussy and this bull gave me no choice.

Took Money For Lez With My Friend

My friend K had been selling herself for sex through a very high priced agency. She looked the part, only the best clothes, shoes, handbags that cost over $ 2000. She's my age, and started when she was 17 with a false ID. She owns her own home already and drives a very expensive car. Contrast me, In debt with student loans, plus behind on my rent in my shitty apartment. She came over last friday night and needed to talk with me. She had a booking for her and another woman to do some lesbian sex in front of this older man. It was a three hour payday. The other girl got flu and she knew that the other women the agency tried to put her with were too dom or too old for this particular regular client of hers. We would be there, strip each other, kiss, fondle, finger each other vaginally and anally, this guy definitely wanted to see both girls penetrated anally. She said I'd not have to have sex with him, maybe he'd want her but I didn't have to. My part of the evening would be $3000. Enough to get my rent and car payments more than caught up. I could even go to the grocery.

I timidly agreed. Her suggestion was that I spend the next two days and nights at her place. We'd get used to each other, which I found out meant we'd have lesbian sex. She was wanting to groom me, make me up, dress me etc. So I looked the part. Well to tell the truth she was great at sex. I never had orgasms from anyone like her. I tried and she says I got pretty good too. She trimmed my brown pussy hair so there was no hair on the outer lips, just from the top of my slit up about 3 inches and an inch wide. I was dressing in her undies, her clothes , her shoes, she did my hair and make up. Then she just paused looking at me the living room. I asked what was wrong and she told me nothing, that I was beautiful. I kissed her and meant it. I was still nervous as we drove to the hotel that evening. She kept assuring me that he'd be glued to the action and jacking.

After about an hour in we took a break, he had cum once with his hand. K went by him to the drink bar and wiped some of his cum with her finger and stuck it in his mouth, he eagerly ate it, then she did the same with my mouth, and then with hers. After a couple of drinks he came over to us. He wanted to touch us and have us touch him. He promised an extra $1000. So he was lighting rubbing on each of us with his hands, K would stroke his cock, even took a couple of sucks on it. Then he moved my head to his cock and my hand. She told him I didn't do men. He stood up, walked away. I thought it was over and we'd not get paid. Instead he came back with another $1000 and I looked at K, she nodded and told me it was up to me. As she was fingering and licking me to orgasm I sucked his very large cock. Actually I've never had one that large. He said he wanted to fuck me, but K told him I'm lesbian only and actually she broke my hymen about a year before with her dildo, I'd not had a guy. Then he threw down another $3000 and said that was all we'd get it was for him to fuck me and for her to suck me clean after.

Looking at each other I could tell it was up to me. As I was being fucked while she was feeding me her tits and sucking on mine, I asked him not to cum inside me since I wasn't on the pill. His answer was that he paid extra and was definitely going to cum inside my tight pussy. He kept calling me a lesbian c**t, and telling me he was going to shoot his baby juice into my fertile pussy and he hoped he knocks me up. To tell the truth, K was rubbing herself and I actually had an orgasm from all the dirty talk, though there was some apprehension knowing I actually could get knocked up.

After he didn't want me cleaning up, he wanted whatever was left after she licked it out of me to stay in me. Dressed and walking out I told her I'd never had one that thick or long before and I definitely wasn't on any BC. We stopped on the way and bought plan B. At home I waited until the next day to go to the back first thing to deposit $ 5,500 my share for selling myself the first time. I still do go out with K personally and we have sex together. I've signed with the agency now too.

After Work Party

I got a call from my wife a while back telling me I needed to pick her up. She had gone to an after work party and had way too much to drink to be able to drive home. I had just left a job and was on my way home so I told her I’d be there in about an hour. I stopped at a liquor store and bought a bottle of scotch and a bottle of vodka and some cranberry juice. I keep an ice chest in the truck for work so I bought some ice and put the booze in the chest.I called her when I arrived and she came out and jumped in my SUV, clearly drunk. She was in a good mood and wasn’t ready to end the night so she suggested we go to a nearby bar for a couple more drinks. She was looking sexy in a short summer dress and I could since that she was going to be ready for sex when we finally got home. We had a couple of drinks then left, driving in the general direction of home, though she still wasn’t ready to go home.

She kept telling me she wanted to have some fun and wanted to go somewhere and continue the party. I drove to a park and we sat outside with the lift gate up and drank some more. Before long, she was all over me…kissing me and rubbing my crotch telling me how horny she was. I kept trying to tell her we should head home, but she was adamant she didn’t want to go home yet. The music was playing in the SUV and she stood up and started dancing for me in a very sexy manner, lifting her dress as she did. I looked around and noticed there were 2 other vehicles parked nearby but I couldn’t tell if there was anyone in them. We were parked close to a light , but they weren’t. I told her about the cars and that there may be people in them but she said “Who cares!” And continued to dance.

As she danced, she slid her gstring down and tossed it on the ground by the car and kept dancing, turning, bending over, and flashing me. Then, she faced me and completely removed her dress and tossed it in the back seat of the vehicle and said “Well, what do you think of this?” I was surprised because this was unusual behavior for her, but I wasn’t complaining. I stripped my clothes off and lay back in the hatch, my legs hanging out the back as she started giving me a BJ. I was just really getting into it when I saw someone walk up beside her watching. A second later, someone else walked up on the other side and stood there watching. I told my wife we had company and she stopped for a moment and looked at them and asked “So, do you like what you see, or are you here to complain?” They both said they definitely liked it so she said “Then enjoy the show, but don’t try to fuck me!”

She continued giving me head as they stood there, both now had their cocks out and were jerking off. I was getting close to cumming, and told her so. She stood up and turned around and bent over, then said “Take me” I stood and stepped behind her and instantly shoved my cock in her already soaking wet pussy. We fucked for a few moments when she needed to turn and brace herself on the car. She had cum once already and was getting close again when one of the guys leaned over and asked if he could feel her tits. She was barely able to speak, so she just nodded her head. This was another first, but clearly she was into it. Soon, both guys were fondling her tits and one of them eventually reached between her thighs to her clit. As soon as he touched it, she shook all over and came again. I finally shot my load inside her and we rested for a minute before I went to get some Kleenex from the front of the car.

When I walked back, she was laying with her head on her arms still bent over and the guys were buckling their pants and I saw cum on her ass and back. They thanked me and quickly left so I helped my wife clean up and put her dress on and we left. I verified with her that the guys had not tried to fuck her, she assured me they did not. It hasn’t happened again since, but it was fun!

My Wife Is A Hot Wife

My wife is a hot wife, and that turns me on, and is okay with me! We have been married for over 20 years, and still has a hot body. I talked her into having sex with my best friend and me together as a threesome. She was shy at first, but then she got into it. We took turns fucking her that night, and she kept having strong orgasms with both of us. She enjoyed it so much that she wants it every weekend now. I also suspect she is fucking other men on the side, because I find her panties soaked in another man's cum many times now. It turns me on that she turned into a hot wife, or a hot MILF. As they say, nothing better than cumming in another man's wife!

All Of Them

I have had way too much to drink and it is time for me to confess something. I have been fucking the truck drivers at my company for years. Yes, I am married and this makes me a bad person. But fuck, I get and have access to so much cock that it is incredibly hard to say no to. It does not matter which guy, when they ask, I fuck.

Bfs Special Wedding Gift

My boyfriend and I got married a year ago. There's this funny custom where the bride is kidnapped at the wedding. That's exactly what my boyfriend had planned. I was kidnapped by 5 of his friends, but what none of the guests knew was that my boyfriend wanted to send me on a sexual journey one last time. In short: they had sex with me. In a basement where they passed me around in my dress and undressed me more and more. My boyfriend stayed at the party and told the guests that I was only changing because we were going on our honeymoon afterwards. None of them knew that I was actually being passed around like a piece of meat in the basement. It was absolutely fantastic and I thank my husband for that...
What even he doesn't know is that I still do it with his friends in that cellar behind his back...

Unexpected Gift On My Birthday

When i turned 18 i went out with my bf and some other friends to celebrate and i *legally* got kinda drunk. But not too drunk.

We had a lot of fun and i was making out with my bf every now and then and teasing each other. I was pretty horny by the end of the night but we didn't do anything. We split around midnight and my bfs dad picked us up. Now i wasnt innocent by any means and i've had many experiences which i dont tell people and i could tell his dad's totally my type.

When we reached their place my bf just went straight to bed while i hung out in the living room with his dad. We talked and stuff and idk if it was the alcohol, that im horny or that i found him hot.. or all of that but we started teasing each other at some point and he had me rest my head on his lap to massage my scalp which was soooo good (but normally i wouldnt even be that close to him).

I felt his boner through his shorts at some point amidst the teasing and it was huge, and definitely poking my head. I turned around to get a better look at it and idk what i said but i got off the couch and kneeled down infront of him and gave him a blowjob. He clearly loved it and said his wife doesn't even do that for him and that im such a good girl. It was so nice and i sucked his cock the best i could until he shot a big load down my throat. The feeling of his cock pulsating in my mouth was incredible. We didn't do more than this that night but everytime we see each other i know we are thinking of the same thing and how much we want to do it again