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:

Set Her Up To Share

About twenty years ago I met my now wife and we were dating. It had begun when I answered her ad on the old CL and she was an oral freak. Loved to suck cock and still does.
Anyway, she lived quite a bit far from me and I'd drive ridiculous miles and hours to see her in the neighboring state. We really connected and had a great time together. We did go places and do things like all couples but we also spent a lot of our time having all kinds of hot nasty sex that involved a lot of 69 fun and even more of her sucking my cock.
Anyway, there was a really nice young guy working at the gas station near her apartment where I'd stop often to fill my tank. I got talking to this guy and mentioned that I was there to see my gf, that was why I came so often from so far away. I told him how she was so sexy and that it was worth traveling for the kind of blowjobs she gave me. I even showed him a pic of her naked ass where I drew a heart with a marker. Jorge told me he was alone in the country and lived in a shared apartment with 4 other men so didn't get any pussy and was forced to just jack off.
Anyway, he was such a nice guy that I asked my gf if she would do me a favor and suck off my casual friend. She was more than happy to help since she is such a cocksucking woman.
I told him that I had a special g*ft for him and that he should come with me after his shift ended one night. I took him to my gf's place and we went upstairs.
I had him go first and he was in for an hour of the best head he ever had.
He walked into the living room and saw my gf lying back across a big old armchair in a filmy negligee that showed off every inch of her soft white body and her pretty pink parts too.
So she was sitting back and toying with a large brown lifelike dick dildo in her ass and her wet pussy was winking at him.
She took the dildo slowly out of her butt and put it into her mouth and gave it a few slow and sexy sucks. Then she slipped it back in her ass and motioned him over and made kissy motions to show she wanted to suck him.
Jorge looked back at me and I totally encouraged him with a smile and a pat on the back and steered him to the armchair and my hot hungry gf.
He dropped his jeans and she slipped down his boxers and said "That looks delicious; give me a good taste please."
Jorge looled like he won the lottery as he fed her his fat brown uncut dick. He was less hairy than I expected but the pubic hair was very black and wiry especially on his balls which were about the size of ping pong balls and she loved sucking on them.
My wife loves to suck cock and to make it cum in her mouth and she always swallows so Jorge got a wonderful bj and I got to jack mine as I watched.
After he came with a roar he thanked us both again and again and he let himself out.
I was all over her and took the dildo out of her ass and replaced it with my average sized dick and gave her a second load.
We haven't done anything like that or shared her mouth for a few years but think we may have to try something like that again for the naughty fun of it.

Dating Older

I have always dated older than my age. I grew faster than every other girl and well, it made me look older.

At 19, I was dating a 38 year old. He was married and it was on the down low. One night he and two of his friends shared me. It was my first multiple men playtime and I was hooked. One hole, two holes and three holes - they did me every way imaginable. When I was 22, I had my second. At 23, I had been part of at least a dozen.

I am 32 and my pussy is always horny. It craves being taken by multiple men. I had my first all black about a month ago. I was left bowlegged and completely used up.

I don’t really know why I am making this confession. Maybe I need some affirmation? Maybe I need to be told I am a slut that is only good for sex? Maybe I just need to get it off of my chest? Regardless, I am real and I enjoy being gang banged.

Is It Cheating If He Gave Me The Ok That One Time

I long time family friend was actually my dad neighbor for a while recently reconnected with me. Found me on social media about 3 months ago and reached out. Hung out a few times had some beers really nice guy that lives next to us for a long time. His son wife Stacy and him sold there house after he got a better job offer out of state but ended up back after it did not work out.
It had been a few years since we had talked and I had grown up moved out and lived on my own. Met at a bar caught up asked me back to hang out. All I could think about was his wife. Growing up I thought she was absolutely gorgeous. Last time I’d seen her I was 16 17 and I remember her work out outfits. Spandex shorts leggings and a fitted tank top long blond hair in a pony tail blue eyes very pale skin. I jerked off to her dozens of times. Fast forward a few years and I’m following him back to his place. Got out followed him through the door he says I’m home look who I ran into to. Stacy walked over from the next room saw me and ran and gave me a huge hug. She never had much on top had small boobs but that had changed. She had a solid hand full and even though it had been a few years every thing else remained the same. She smelled amazing I felt like the little teenager again. Dick was almost instantly hard. All I could do was to check her ass out. It looked as if it might had gotten a bit thicker but it looked good. We had a few drinks and that evening and to an end but was invited back the next day for a bbq. Went home rubbed one out and then came back the end day. I walked into the back yard Stacy was on the grill short as denim skirt tank top not bra nipples where poking through the thin material. Her husband walked up or staggered over apparently he likes to put it down and started early. He sat there quiet while Stacy and I bbq. I kept seeing her skirt slowly rise up a few times as she leaned over her husband wasn’t paying attention so I had my phone out and was taking pics and videos. Her thighs and legs where thick at one point I had a clear view her rear from the back side and her thing all but disappeared between that thick ass. With his encouragement he teased her about showing off she turned beat red and I kept quiet u til he said it’s just us slurring his words he said I’m tired you guys have fun Stacy looked at me and said that he meant we could have some fun if that’s what I wanted. I pounced and went directly for their ass. Up the skirt went licked and ate and finally fucked her there on the patio. The music playing hardly covered the noises and moans she was making. It was as good if not better then what I expected. The rest of the evening I blocked her off my cock and after a few more drinks on her side I tasted and took her ass as well. That was a few weeks ago since then she comes over and lets me put it down on her. Likes it rough likes to have her pony tail pulled and likes it doggie. The more we hang out the more she opens up. She’s a chatter box especially right after an orgasm. She told me that she wasn’t a little wild when they moved. He has always been into watching her fuck and a few of his new work colleagues got a chance with her and it went a little wild. She said that word got out and most of the guys in his office wanted to hang out with him. Before he knew it most of the guys in his office had tried to or fucked her including her boss. He did fuck her and at one point tried to get her to leave him and stay with him. That was the last straw and he quit and moved them back. She said she never went out looking for sex he always brought guy around and at times he would let them fuck her. Her body count was high but it didn’t matter I got turned on hearing her story and pounded her into my mattress. She makes these little sounds and begs for it. It works because I nut so hard. I can see why you’d want to try and keep her. She gets so attached that I bet she decides to leave on her own. That’s why he was so quick to put a stop to her. It’s gotten so bad that she’s already at my place going to town waiting for me. I often walk into my house with the noise of her fucking herself with a dildo. I’m going to ride her for as long as she lets me.

Hot Wife And Her Boss

My wife has worked for her arrogant boss since before we met. She told me when we were dating that she is sexually submissive to him and he takes her anytime he likes. He shares her with clients sometimes too. She gets bonus pay for sucking cock and for anal.

Anyway, I found out early that I was very excited to hear her tell about being a whore for her boss Pablo. I love to kiss her and finger her and have her tell about him shoving his dick down her throat and how he encouraged her to let a client fuck her ass very hard and deep.

I like to lick her used holes and soothe her sore anus with my tongue and lips. Rimming her and listening to her moaning and begging for more. Telling me that Pablo's big fat hairy dick makes her cum and my ordinary dick doesn't cut it.

She says some day she might have Pablo fuck her in front of me and make me suck his dick and clean his dick after anal.

Mandy's Desires

My wife Mandy has just gone to bed completely knackered.
That's because I had five of my mates around last night and the last two have only an hour ago left.
From around ten o'clock last night until an hour ago we all took turns fucking my wife.
At several points during the night and into this morning there were three men fucking all her holes.
Plus we took turns alone to fuck her.
It was her thirtieth birthday and a gang bang is what Mandy said she'd love to experience.
So I set it up and boy was it an amazing sexual time.
At around two in the morning I went to bed leaving our remaining two friends to carry on fucking Mandy. They used our guest room and I could hear them fucking as I drifted off to sleep.
Apparently they slept a little and then began having sex again.
They were spit roasting my wife when I walked in on them earlier on. I joined them with my morning glory and used my wife's freshly fucked arsehole to dump my load into.
My friends left an hour ago, but it didn't stop me from enjoying my wifes mouth and pussy before she showered.
We talked after her shower and she said that particular desire has been well and truly fulfilled.
She mentioned she doesn't think she'd want to do it again as she's sore (especially her arsehole), but then I reminded her we're going on holiday in a couple of months to Barbados.
Her smile said it all. That's because one of her other desires is to enjoy an older black male.
We'll see if that happens when we're there.

Sharing My Neighbours Wife

After a neighbour of mine had an accident I did a bit of gardening for him and his wife Penny.
They're both in their mid fifties and if I do say so, Penny is still very attractive at her age.
I'd spent about four hours sorting both their front and back gardens when Mr B asked me if I wanted another drink.
Telling me Penny had made me one inside, he sat on the rear patio seats drinking his cup of tea.
When I walked inside into their kitchen Penny was completely naked sat on a breakfast bar stool and she was playing with her pussy.
All she said and I remember these words precisely "We haven't got the money right now to pay you for what you've done, and **** wants you to fuck me in payment of services".
I probably should have said no, but I wouldn't be here telling you if I did.
I got an erection looking at my beautiful neighbour and within seconds we were kissing like lovers as Penny reached for my cock through my shorts and I played with her pussy.
We'd been kissing for about a minute when Penny's husband walked past saying "Don't mind me, I'm going down to the pub for an hour".
We stopped kissing, but by then Penny has my cock out and that's when Mr B said "She'll enjoy that".
Penny and I licked, sucked and fucked over the next hour, with me cumming in her twice.
I even got to fuck her tight arsehole, something she later said her husband hadn't done for years.
The following day Penny knocked on my door early and we had sex in my lounge.
I fucked her like she was a whore and trust me she loved it.
As for Mr B when he got back from the pub the day before half cut, he told me "Anytime you want to fuck my wife, you're welcome". Penny smiled at him and sarcastically said "Thanks for the permission ****, but I was going to have him anyway".
And so over the past year myself and Penny have been having sex pretty much every other day.
And some nights she'll stay over. I've never met a woman with a sex drive like hers and it turns out I'm most definitely not the first younger man **** has had fuck his wife. In fact I now know Penny has a lover who she meets every now and then in the next village.
In a couple of days time she's invited him round. **** doesn't like him so he never visits, but **** is going into hospital for a procedure and Penny has asked me if I'd like to enjoy a threesome.
I've never met her other lover, but I'm more than up for some double fun.
If it goes well, and I don't see a reason why it shouldn't, I'll let you all know how it went.

Sharing Is Caring

My wonderful wife has been a dp freak for many years. She loves the feeling of fullness and I love feeling another man's dick rubbing against mine separated only by the thinnest membrane.
She loves leaking into her knickers from both holes and telling me about how it feels.
I also love hearing from men whatever they will do to my wife and how good her mouth or her kitty or her arsehole feels on his dick.
Hearing them say "Your wife can really suck dick, man." is super exciting to me.

I Accidentally Got My Girlfriend Pregnant

So I've accidentally got my girlfriend pregnant and the strangest thing about the whole thing is how much it's turned me on. The fact I've managed to breed her and the thought of her body changing and growing with my seed gets me rock hard. I can't understand why is this a primal thing or am I messed up.

Threesomes Discovered

I’m a sports physiotherapist and I’ve been having an affair with one of my clients for almost a year. I am more afraid of getting in trouble at work if we get caught than I feel guilt about cheating on my husband. He’s fat and has let himself go. Simon on the other hand is a 6-foot-4 former Olympic swimmer who does triathlons. He lives near my daughter’s school, so at least once a week after I drop her off, I go to his house. The fucking is incredible. He’s a sexual athlete with a big uncircumcised cock that’s always hard. One afternoon we fucked five times. I couldn’t believe how much he came.

Since we started I’ve become more uninhibited sexually, sometimes letting Simon pull my hair or choke me when I’m coming. I have always been bi-curious, and made out with a few other girls in college. So when Simon suggested the possibility of having a threesome, my ears perked up. He said he knew an ex-girlfriend who would be interested, so I agreed to meet her.

That Sunday I told my husband I had to work at the clinic. Simon and I met at a coffee house near his place. Krystal arrived shortly after, and I was immediately intrigued. She’s a gorgeous Black woman with dark skin and long, curly hair. She was wearing a tight polo, a short skirt and long leather boots. I was a little nervous, but she put me at ease with her demeanour. The three of us talked for an hour before Simon suggested we go back to his place and smoke a joint.

That was a great idea, because it relaxed me even more. The three of us started rubbing each others legs, taking turns kissing. Then Krystal had an unusual request. “I want you two to fuck in front of me,” she said to Simon and I.

He has a large ottoman in front of his sofa we’ve fucked on dozens of times before, but this time Krystal would watch us. I usually like to start on top with Simon to let his long thick cock impale me before he flips me over and finishes me like a jackhammer from above. That’s what we did here, except he went slow with languid strokes. Krystal rubbed her nipples and fingered herself watching us, but eventually stripped off all her clothes except her boots and joined in. Straddling my face, I tasted her pussy as Simon picked up his cadence. I came fast, and when Simon was about to come, Krystal grabbed his cock and aimed it at my tits.

Simon needed a few minutes to reload, so Krystal and I explored each others bodies, ultimately 69ing on the ottoman. Then she reached in her purse and pulled out a large strap-on.

“Simon always told me he wished he had two dicks” she giggled, as she started stroking his cock back to attention.

He then put on the dildo around his belly button, giving him two identical-sized big dicks. Krystal got on the bottom to take his cock and I laid on top of her to take the strap-on. As he fucked both of us vigorously, Krystal reached around and rubbed my tits. It was suddenly really noisy with all three of us moaning and grunting. Krystal’s booted knees were up and my legs were in the air on top of them so far that I was almost doing a backwards somersault as he pounded us. I turned around to face Krystal on top of her and sucked on her tits as Simon kept thrusting into us. Climbing up onto all fours as the strap-on made me come, I looked down and watched Simon pull out of Krystal and ejaculate his white semen all over her black stomach.

We smoked more weed and fucked one more time, with Simon on the bottom. I reverse-rode him and laid down on him, while Krystal laid on top of me in the 69 position. As Simon’s cock punished my pussy, Krystal tongued both my clit and his shaft.

I came so much that my skin was pink for hours. Krystal and I had bonded physically and I was hooked. The following week we went to her place where she has a sex swing. Simon put me on the swing and fucked me while I rolled back almost upside-down and ate Krystal’s pussy.

Simon and I are now talking about having a threesome with another man.

Nanny Talk

Last week sometime, I posted an experience regarding our live-in nanny, who had found a toy of mine in my bedside table, which also happened to be a clone vibrator of my husband's penis. It was a fun couple's activity we did together on Valentine's Day but actually became something that I have enjoyed using often since.
Our nanny is in her early 20s, and in a new foreign country alone, so I understand the loneliness. I wasn't mad and was actually intrigued and turned on at her using it. I wasn't sure how to proceed about the incident, say nothing or mention it etc. I didn't want to make waves, since she has become a really good friend to me, and she is really good at what she does.
I decided to say nothing and see if she would bring it up, which she didn't and hasn't. I sat talking to her the next night after the incident and was just casually talking about her experiences etc. During the talk, her social life was mentioned, and I asked her how things were going? She seems to have sort of taken me as a mom away from home situation. She talked about being lonely but making friends, males included, but nothing serious. I made a point to tell her that I was always around and willing to talk about anything, emphasizing ANYTHING. She laughed and said that she hoped that someday she would have a family life like we have. When pressed what she meant, she said the usual, stable comfortable life, growing family, then something I found interesting. She mentioned that her parents slept in separate beds while she grew up, and that it was nice that hubby and I seemed to "really enjoy each other"? She mentioned that sometimes she ventures downstairs to the kitchen to get something to drink or eat after everyone has retired to their bedrooms. She said she loved to hear hubby and I in our bedroom talking and laughing and basically "enjoying each other".
Our home is laid out that the kid's bedrooms and the nanny bedroom is down one wing of the upstairs. Our primary suite is down a different hall on the way to the staircase leading down to the main floor kitchen etc. If she goes to the kitchen after the kids are asleep, she could very likely hear us in our room as she passes by. I never thought of this, but we make sure that when the nanny is on her own free time, we don't bother her and take care of the kids ourselves in case they need anything during the night. Because of this, we don't leave our bedroom door completely shut but rather cracked in case one of the kids has an issue or is crying and we need to go deal with them. After chatting with our nanny, I was curious so last Sat night the kids were asleep soundly, the nanny was in her room, and hubby had returned from a 5-day work trip. I mentioned during the day to the nanny that I was "excited for his return" hoping that she would understand what I meant. I have been aroused by her ever since this experience. I made sure that our television was off, and my bedside lamp was on as I crawled nude into bed next to my husband. He quickly stripped off his sleeping clothes and we began to explore each other with our hands. It was an unusually warm evening for the spring and since the AC hasn been turned on yet it was warm in our room. It was perfect for me to roll down the covers and let him stroke and knead my breasts and lick his way down to my damp pussy. We were both nude and on top of the bed, I had left our door a little more open than usual and I noticed I could just see a bit of the hallway reflection in the glass of a framed painting just outside of our bedroom.
As I laid there on my back feeling hubby parti my lips and licking me, I watched the reflection in the art and noticed, not even 10 minutes into this, our nanny's reflection, as she stood a bit down the hall, listening, but then realizing she moved close enough to watch through the slightly open door. My hubby had his back to the doorway so he couldn't see the nanny outside our room, and I acted oblivious. I looked down shortly after and could see hubby's shaft fully erect and so I moved into position to suck on him as he sat on the bed on his knees. I was giving our voyeur a perfect side view of hubby's body as I licked and teased the drips of precum from hobby's hard swollen head. I quickly pushed him onto his back, the angle that I was laying before, and quickly got on top of him and really began to pump up and down. I could feel him getting harder and warmer inside me, so I hopped off and sat reverse on top of hubby, blocking his view of the hallway and also allowing me to see if the nanny was still there. Surprised or not surprised I could see her reflection still watching us. Hubby was gripping my hips with his hands really pulling me against him. I was massaging his balls and could feel him beginning to pulse. Just as he began to spray a fountain of warm sperm, I pulled him out. I let the nanny see it all. I'm shaking still as I write this and really turned on.