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:

20 Year Reunion

This confession is actually 2. Last month was my 20 year college reunion.

20 years ago, I was part of a mmmmf gang bang. My boyfriend at the time and his three roommates all fucked me after a frat party. It was a one time thing in college, although I may have done this sort of thing in my adult life too.

At my reunion, I found myself standing in a room with three of these four guys. My mind went back to that one night and I was in trouble. Lots of discussion about college memories, including the four of us talking about that night. Two drinks later, we all agree to going back to my hotel room together. Two of the guys are married and so am I, but we did it anyway. By 3:00 in the morning, I had been gang banged and now was alone in my bed.

First Hand Job

I have been practicing massage therapy for 10 years. It is my job and I take it seriously.

I am doing a session with a new client. He is a very tall, fit and good looking guy. When I turn him over to his back, his penis is semi hard and fucking huge. I mean, I could not get anywhere near his left quad because was just laying there.

The next session I have with him is the same thing.

The third session is where it went wrong. His hands or fingers touched my legs, ass and pussy whenever I was close to the table. My black stretch pants were no barrier at all. One time I purposely allowed my pussy to linger by his hand to see what would happen. I felt his fingers reach for my pussy and touch it. I just kept rubbing his back. He got more bold and took bigger swipes at my pussy. I had crossed over into the not okay zone, but I did not care at this point. This went on until I turned him over.

As I turn him over, he is rock hard, leaving the bulge in the sheet. Again, his hands found my body. As I rubbed his quads, my mind summons the courage to touch it. Holy fuck, big, heavy and rock fucking hard. I grab it and stroke it. He finds my pussy and I give him better access. I finally take off the sheet and there it is in all of its glory. I jerked him off and he rubbed my clit through my stretch pants. We both came hard and heavy. That day I broke an ethics barrier.

Since this client on this day, he always gets this treatment. I have three other hung clients that get this treatment as well.

Tasted Both

I confessed here about 6 months or so ago about my mother in law moving in because my wife Erica was pregnant and since we were expecting our first her mom would move in to help us. Her mom and i stared am affair way before I met my wife. We met at the gym and i had been fucking here for a while and during Covid she lost her husband. Before that she had introduced me to her daughter so I could spend more time together. It worked but Erica and I hit it off. She is a younger version of her mouther gorgeous. In bed they are almost the same although I can get her mom to cum from a good ass fuck and my wife takes it but has yet to squirt like her mom. During the pregnancy we got the room ready and once the baby came my wife and the baby slept a lot and I fucked her mom non stop. It’s been around 6 months and it’s been fun today the least. Her and her mom are close Erica does her best and I love her for it. Sex with my wife is very intimate and she likes that I am very romantic with her. Every once in awhile she likes it a little rough. Her mom on the other hand likes me to take it. I mean grab her by the hair slap her ass over and over and force it in one of her holes. Mouth pussy and ass in any way. My dick has gone from my wife’s right ass to her moms mouth. Both women walk around in shorts or leggings and a shirt. My wife’s tits have milk in them which I love to suck on. One of my favorite things is when they go for there walks with the baby and I know both mom and daughter have cum leaking form at least one of there holes. It’s fun and I’m sure that her mom is permanently moving in with us. I would totally love to get them in a bed and have them fuck each other. Her mom knows I’d want this but not sure of the wife would be ok with it. I’d hate to fuck this up.

Two Problems

Over the years, I have figured out that my mom is a total slut. The amount of ‘boyfriends’ she has brought home and fucked is countless. This is problem one, my mother being the town slut.

Problem two is me becoming a slut too. My mom is completely open to me bringing guys home to fuck. Listening to her over the years has encouraged, welcomed, made me comfortable with slutty behavior. At 23, I have given head or fucked over 100 guys (boys, guys and older men). I know this isn’t acceptable behavior, but it seems impossible to stop reaching for more pleasure.

Wifes Satifacation

Me and my wife have sex often but she recently told me I don’t satisfy her , so I hired two guys with big dicks , and we fucked her all night , I watched and jacked off , I did her last at 6am after the guys left , she said that was satisfing sex and that’s how we have to do it now , it takes three dicks all night

Travel Soccer Trip

My 16 year old daughter and her travel soccer team were invited to a tournament in Florida. We loaded up the cars and we caravanned south.

The set up was premier - soccer fields, hotel and a small convention building in the middle of a large enough town. Everything was brand new from the construction of a few years ago.

Connie, one of the other mom’s and I made our plans together. We drove down in my suburban as it gave us ample room for equipment, bags, food and space to spread out during the drive.

We stayed in the same suite - two 16 year old girls and the two moms. On the second night of the tournament, there was a players only buffet banquet in the convention center. It started at 6:00 and would go until 11:00. Connie and I planned to go out to dinner with a few of the other parents. We never left the room.

Connie and I have a very close and sometimes cheeky relationship. We are both divorced. We both have our own money. We both work, but we have the flexibility to do things like this soccer tournament.

As I got into the shower, Connie asked if it would be okay if she got ready in the bathroom as well. I didn’t care. I am washing my hair and I realize she is naked. As I start to rinse my hair, I hear her nails tap on the glass door. She says I hope this isn’t too weird, but may I join you? I paused, apparently too long, so she backtracked and apologized. I stammered to say I was sorry and that she could join me. I found myself in the shower with another naked woman. Connie is an extremely fit 38 year old woman. She is 5’7”, olive colored skin, deep brown eyes and brown hair. Her boobs were a handful and her nipples were on the smaller side. She was shaven, with the exception of a landing strip. I am 5’’11”, blonde hair and blue eyes and thick. I have large boobs and a nicely trimmed bush. I am an imposing woman - a volleyball player in high school and in college.

As we get past the awkward, we take turns under the shower head. I was surprised to feel her hands begin to soap my back. We exchanged this ‘help’ and even hosed each other off after shampoo and conditioner. During this help, she cleaned my pussy. I was frozen as the bar of soap pressed on my lips and my clit. As Connie did this, I could not help my breathing heavy. I did the same to her while soaping her body. We finished our shower, helped each other dry off, texted our dinner party that we were not coming and found the bed. No sooner did I hit the bed was Connie kissing me. I opened my mouth and allowed it all to happen. My hands found her naked skin - boobs then her pussy. Her pussy was slippery and creamy. She was obviously horny and ready. I pushed her on the bed and went down on her. She came two times before giving me the same treatment. We finished the night with room service and a movie, all the while touching our legs, feet, hands and pussies. We played one other night during the trip.

When we arrived home, I wasn’t really sure how this would work. As she got out of the car, she blew me a kiss and told me to not be a stranger. Connie and I play now and then. It is always immensely fun. We are convinced that nobody else in the world knows our secret.

My Dildo Mistake

Like many many many other women, I have sex toys. Like many many many many other women, I have sex toys for specific needs and uses. When the need to be fucked silly comes upon me, I use my 9” black rubber dildo.

I am a widow. I have two sons. One is local and one is about three hours away. The local son stops by every once in a while by himself during the week or with his family on the weekends.

Last Tuesday night I used my dildo on myself. I just needed to be pounded. Well, the next day when I got home from work, my son was at my house. In panic mode, I struggled to remember if I had put the dildo away the previous night. As I entered my house, my son was in the living room waiting for me and playing on his phone. We said our hellos and went to the bathroom to pee. And there it was, covered in a dried white sheen, sitting on the vanity. I looked in the mirror to see how red I was. I was humiliated - had my son seen it? Yup, the toilet seat was up.

As I came out of the bathroom, all I could say was sorry you saw that. He responded and said it was our story and to not worry about it.

I will have to be more careful with my toys.

Shameless

I'm a 63 year old widow, 8 years. Own my house but money is tight.
I'm shamelessly sucking off and getting fucked into the headboard by my 52 year old married neighbor as a thank you for the projects he does around the house for me.
I do pay him some cash money so his wife is satisfied that he's not working for free but the fact is, he comes over to tackle any small project and I blow him when he walks through the door. When he's done, I'm in whatever position he wants me in taking a fucking that leaves me sore for a day or 2.
I do guilt about it, especially since his wife is a really nice woman and we are friendly, not friends but friendly. I actually really enjoy the sex though. I never swallowed for my husband but he made me and I've come to actually kinda like it. Never shaved my pussy before but I do now because he won't lick or fuck me with hair.
He makes me thank him and I do. It's purely sexual, nothing more.

She Lets Me

My friend from school Mathew has been hanging out with me more and more lately. He is married with twins. His wife can be a handful some times and he likes to have me there to probably make things easier at home. Lindy his wife is a good looking women. She was smoking hot when they met and after kids she gained some weight lost a bit of it. She is a short thick blond big tits big ass some people like this some people prefer sticks. I think she has a smoking body my buddy tells her to lose more weight. One afternoon we are in the garage watching college game day and after a few beers Lindy comes out and sits on the couch next to me and we are all watching the USC game. They start in on each other my buddy goes to grab a beer and we are out. While they chirp back and forth with each other he lets go and brings up her weight again. There is a store at the end of the block and he says I’m going to walk over and grab more beer anything else we need. I say to grab sandwiches form there deli so he agrees and walks off. Lindy and I are talking she is pretty much mother fucking him I tell her to calm down he doesn’t mean it. She kind of started crying and says he does and she feels horrible about herself. I tell her that she is still hot and she should show off her stuff more and he would probably like that more. I know I would is what I said. She was in a tee shirt and shorts. Her outfit while it was not sexual appealing didn’t look bad on her. Joking I said show off those massive tits more. All she aid is they are saggy and no one would want to look at them. Your nuts i said and I don’t know why but I reached out and grabbed one. No bra with a thin t shirt it felt nice. Big really big tits the kind that I don’t realize how big it was until it’s in my hand big. She sat there looking at me so I grabbed the other and squeezed and pulled. I slid my hands under her shirt she lifted it up and I played with her tits. She said that felt good. Good to be touched and wanted. Tits where out she leaned back and i started to suck on them when i realized that she was lactating i sucked each tit and my hand found its way up her shorts that where loose and I slid right into her now sloppy wet hole. I stopped and out her shirt down and she said no don’t stop. I said your hubby will be home soon. About 10 minutes later he showed back up and we had our lunch and he had more beer. Enough that he dozed off on he recliner and I made Lindy give me head before she rode me while I sucked more milk out of her. At one point I handed her my phone while she was on her back shirt off in the missionary position legs up on my hands tits swaying as I pounded away. To keep quiet she shoved her panties into her own mouth and flooded her pussy walls with cum. This happened back at the end of August and she just told me that her monthly visitor is 3 weeks late and she hasn’t had sex with her husband in a while. So I think I may be a dad soon

You Missed Out!

To the guy below title "Big Mistake". Yes, you did mess up big time. By not jumping in and having one of the best experiences EVER!
Me and the wife were swingers back in our 20's. Yes wife did enjoy BBC. We actually had a regular guy wife liked very much. I loved seeing his black cock working her over.
One afternoon we decided to have a picnic at a wooded city park. We invited our friend. Grill our some steaks, have a drink then go to a hotel after. Well the wife was getting some sun in a bikini and the guy was getting horny. Our picnic shelter was somewhat secluded, but not private. I was tending the grill and I noticed they were sitting at the picnic table making out. As I kept checking up on them things were progressing. It didn't take long before her bikini bottoms were around her knees and he had her bent over the picnic table fucking her little pussy. I loved watching so I went over and got a surprise. He wasn't wearing a condom! Up until then we always used condoms with others. I watched him pump a huge load inside her. When he pulled out I got behind her and got a great view of her gaping pussy starting to ooze cum. It made me rock hard! I immediately shoved my cock inside her. Her pussy was loose and slimy! It felt amazing!!! I shot my load in record time.
Yes you missed out!