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:

Wife Told Her Husband To Pull Out And Let Me In

Found this nice swinger couple online and decided to meet them on their vacation. The wife and husband get naked and start having sex. I'm just watching waiting for them to invite me in. Something I was told to do before hand. This way if they don't feel comfortable with me joining then I just get to watch.

Anyways, the wife is riding the husband and after about 15 minutes she says I can join in and asks me to put it in her ass. I drop my pants and go to get behind her when the husband notices the size of my dick. It's not huge but it's bigger than average for sure. The husband stops me and asks his wife, "are you sure you want that in your ass" and she starts moaning saying no I want that in my pussy.

The husband is all excited and gets up as I'm laying down and his wife crawls on top of me. He helps guide my dick inside her and she just holds me tight as I put my dick all the way in. The husband gets behind her and starts fucking her in the ass as both fuck her and make her cum.

Next thing I know the husband pulls my dick out, puts his back inside her pussy and blows his load inside her with me laying underneath. When he finishes he puts my dick back inside her and goes to sit in a chair to watch.

I make sure to give him a good show. I hold make until the wife is telling me I can cum. I pull out and cum all over her tits. All in all a good night.

On a related note if you're a young, fit, and somewhat hung bull it's easy getting pussy these days. All these cucks will give you their wives. I've only been in the community a month and this is my second time with a couple and both experiences have been good.

Odd Request

Last Friday my wife Genna (37) and her friend Allison (40) where hanging out at our house, just drinking and talking shit about their co-workers. I come in from doing yard work at about 8:30 and get quick shower. I walked into the living room in my gym shorts and a T-shirts, and Ally starts whispering to my wife. I ignore them for a bit then Genna says, why are you hard. I wasn't, maybe a half chubb, but definitely not hard. Anyways I said, well, the two hot milfs sitting in my living room seems like a good reason to be hard.
Long story short, after a lot of joking back and forth my wife pulled my dick out and started to play with it. I would've loved a threesome or even a blow job, but only got a double handy. Still, it was nice having another woman's hand on my dick after 12 years of just my wife's. I busted my nut all over their hands and they licked it off of each other's fingers.

Still Wondering Why

Two weeks ago, my boyfriend and I went out to the movies. We got home around 11:00. When we got home, I was horny - like really bad horny. My boyfriend did his best, but was not even close to taming my desire. He says to me, I could ask my friends to come over for a one time fuck. I am sure at least one will come over. Those jackasses…four came over.

One by one they started showing up. My boyfriend would not tell me who was coming which was mean, but naughty too. Eventually, the four of them got there. So now what I said? My boyfriend, another jackass, says you asked for this, now do your part of the deal. My pussy and brain fought hard, but my pussy won that night. They all fucked me one on one and as a group and they all got head from me. Since then, we did that sort of night one other time….but fuck, I need another one soon!

Pussy Squirting

My new boyfriend and I are on my bed fooling around the other night. I am on my back. He is standing next to the bed with his cock in my mouth and his fingers in my pussy. He is really deep in my mouth and throat. Out of nowhere he grabs both of my legs and rolls my hips back. He hooks my legs behind his arms and literally had my pussy and ass on display. He starts to finger fuck me mercilessly. The feels in my pussy are different. The cock buried in my throat feels different. The orgasm is building. He is literally fucking my pussy with four fingers, but in such a way that it is terrorizing the inner part of my clit. His fingers are thrusting on my inner clit and I start to cum. He never stops hammering…..and it happens. She starts to squirt and all that does it encourages my boyfriend to hit it harder. And bam…like a jet, my pussy explodes juice all of him, me and my bed. And he keeps on going. No mercy. I never stop cumming and the squirting continues until I literally beg him to stop. I rolled over on my side, thoroughly out of breath, asking him what the fuck was that? He said, you can have that every day! Fuck! I love him already.

Disclosure Of Her Past

My wife got herself absolutely drunk a few weeks ago celebrating her thirtieth birthday.
When we got back home, even being unbelievably pissed up, she still wanted my dick. But during our fuck, when I was shagging her pussy from behind, she cried out another guys name.

We carried on having sex and I eventually came all over her beautiful large tits. Once we'd settled down, both having cum, I began asking my wife about her previous boyfriend's. And to my utter shock, she revealed she'd had sex with over forty older men.

It took some coaxing for me to get her to divulge things about what they did, and who they were, but as she slurringly spoke, I got incredibly horny.
One of the men, a guy called Adam, was the person who's name she'd cried out earlier. And it appeared from her words he has a really big cock. It also appeared Adam is now in his sixties.
Persuading her to go into detail, she blurted out he liked to fuck her arsehole when she'd meet him in her younger yeaes, bunking off college some days so they could fuck outdoors.

This was a side to my wife I never knew about, even so I was that turned on, I flipped my wife over, tongued her arsehole for a few minutes, then fucked her rear hole.
She moaned and squirmed about, but I just hammered her arsehole and I couldn't stop imagining all those older men fucking her.
When I came for the second time that night, I filled her backside with my cum then let her crash out.
The following morning my wife had a huge hangover, but asked me if we'd had anal sex. She literally couldn't remember anything of our conversation or us fucking, twice.

A couple of weeks ago I actually met Adam in a cafe. It took a little digging, but I managed to contact him. He let me know my wife was a real cock hound back then and loved anal. As he spoke, I could tell he'd love to fuck her again, but I didn't say anything immediately. Before we left the cafe however, I couldn't help myself and asked Adam, if he had the chance, would he fuck my wife again. His response was "In a heart beat".

Last week during a very horny fuck with my wife in our kitchen, I slid my cock up her arse. As soon as she pushed back, I asked her if my dick filled her backside as much as Adams did. She was surprised and tried to pull away, but I held my wife and fucked her even harder. At the same time I told her about our drunken fuck and what she'd said about the older men she'd had sex with. I also let her know I'd met Adam and he'd told me he'd fuck her again in a heart beat.
My wife stopped trying to move off my cock then and backed onto it. I could tell she was nearing orgasm, so I told her to imagine Adam screwing her arsehole instead. I swear, when she came she shook so uncontrollably and said "His cock is so big".

It's not happened yet, but I've arranged for us to meet up with Adam outdoors. My wife and I haven't stopped fucking since I arranged the meet. It's this coming weekend and to top it all, we're even meeting him where they used to fuck.
I'm not sure how I'll react watching my wife being fucked by another man. But you know what they say, you should try everything once.

Something New At 60

I have had a very good life. I have raised four children. I have been happily married for 38 years. I have worked for the same organization for 38 years. I am nearing retirement. I have the house I live in and a house on a ski mountain. I have traveled seemingly everywhere. So why am I writing a confession here?

About a year ago, my husband and I went to one of those hedonism resorts in the Caribbean. It was clothing optional and I decided to go nude. My husband, well, he thinks I am hot as fuck, so he was like ‘yeah!!!!’ Silly man. He went nude on the beach, but nowhere else.

We met the staff assigned to our room the first day and they were great the entire time. Helpful, courteous, prompt.

As the first day finished, including our travel, we hit the bedroom early and tried to sleep. My husband had other ideas so we had sex and went to bed. The sex was different though. It was free, natural, open. We left the sliding door open on accident. When we realized it, it turned me on even more knowing people may hear or even stop and watch. We fell to sleep naked after closing the sliding door.

We woke up the next morning, showered together and we fucked in the shower. My husband was hard as a steel rod. My pussy came violently twice! We pounded on me like never before. It was magical.

We go for breakfast and my pussy is raging. So many sexy bodies in the restaurant that spilled out into the pool area. After breakfast, we found our chairs, stripped down naked and enjoyed the day. On and off, our staff would stop by and ask if we needed anything. We had other couples stop and talk as well.

Very late in the day, we met Alex and Robbie. They were in their forties and openly sexually liberated. They were swingers for 15 years and basically had an open relationship. We enjoyed their comlany and decided to meet them for dinner. I cannot leave out these details: Alex is a smoking hot, innocent looking teacher and Robbie is a very hung, blue collar, business owner.

Dinner was fun. The food was great. The company was way better than I thought we would experience. We lingered, talked and then it occurred to me: I had not looked at my husband in 30 minutes, sans a glance here and there. I made mention of it and true to my wonderful husband he says, I am sorry too. I have been distracted. Alex and Robbie (and the two of us) all started to laugh as it was apparent we all were distracted.

We started to feel pressure to leave the busy restaurant. As we stood up, Robbie says to my husband, may I escort this beautiful woman to the beach? My husband, always the smooth operator, says only if I can escort this beautiful woman to the pool. I am 60, smart, intelligent, horny as fuck - I know what is happening here. My husband, who must have realized what may happen, gives me a kiss and whispers ‘is this okay’ in my ear. I said yes, if you are. He said yes and we all went our separate ways.

Robbie was clean cut, fit, hung and a perfect gentleman. If I was going to sleep with someone else, he would be the choice. As we got to the beach, he asked if I wanted to go for a swim. I gave an over dramatic ‘no way, there are animals in the water that I cannot see’. He quickly says ‘come with me, I will protect you’ He drops his shorts and golf shirt in the chair next to us and heads for the water. At this point, the only thing protecting that hung cock from being inside of me was my linen cover up. I was steamy and drenched between my legs. If I went into the water, he we be fucking me in no time.

Like a damsall in distress, I said as you sure you will protect me? He said of course. Off come my cover up and to the water I went.

In no time, we were kissing and touching. His cock, when soft was hung, was the largest cock I ever had in my hands. He was 9” or so. His sack was tight. He caressed me everywhere. When he found my hairless mound, his fingers went deep; so fucking that within a minute I started to cum. I hung on his shoulders for dear life as he made my knees buckle and made me howl like a wolf in the wild. I came twice in the water. I rammed my hand up and down his shaft like I was priming a pump. He stopped breathing, tightened up and let out a fire hose load of cum into the ocean.

We decided to head to his room (hubby went to our room). We got there, showered off the ocean and fucked until the sun came up. This man and his cock hit my pussy in spot that had never been hit. I was in heaven…complete heaven. He came two more times that night and I came more than ever before (I lost count).

We spent the rest of the week playing like this. It was hot, fun, open minded and so satisfying. This was the best vacation ever.

Best Sex Ever - Not My Proudest Moment

Memorial Day weekend kicks off summer, especially on Long Island. My best friend invited me to come with her, her boyfriend and her boyfriends friends to a club at a popular beach town. They knew someone who is renting a house for the weekend so we planned on crashing there when we were done at the club. Here is the problem…my friend and her boyfriend found a room to go fuck. That left me with five other people who I do not know and all want to fuck. I made an issue of it to my friend and she tells me (as her boyfriend is fucking her) there is a box of condoms in my purse. Take the whole box into the living room, get undressed and fuck them all. Now leave me the fuck alone!

I stood there speechless. She is getting railed at this point. I grab her purse and unzip it to find a a handful of condoms. She says again, leave me alone and go get gang banged.

I take the condoms, toss her purse on the chair and storm out of the room.

I get to the living room and I say okay, Martitza says I should get gang banged, so here I am. Who wants me?

These five men banged me into a sexual stooper on and off all night. I looked like a wounded animal in the morning when we headed home. I smelled like a whore and my three holes felt like they had been driven through with a semitrailer.

That was a couple of weeks ago and my mind is torn over it. It was consensual by everyone. It was enjoyable. Nobody got hurt. But I feel like a slut. But I want it again. Just some weird event that may linger for a while.

Big Secret

Saw a post below this about a woman who didn't tell her husband about something bad that happened to her. Well I am kind of in the same boat.
I am only 26, married four years and I am now pregnant. My husband is thrilled about the pregnancy. Problem is there is a good chance the baby is not his. And an even bigger problem, the baby might be black.
I don't have much experience with men. I had only had sex with two men until recently. Or office brought in a temp to temporarily fill in for a guy who had a surgery. He is black and I will refer to him as "Tim". A couple of weeks into his arrival the girls in the office started to gossip. Apparently, Tim had managed to bed a couple of the girls and they were not shy about describing his manhood. And the work "huge" was used. As I said I had only been with two men ever, and both of them had a small penis. I started to fantasize about what it would be like to be with a well endowed man.
One day Tim started flirting with me and I started melting. I agreed to go out to lunch with him and during the meal he came on to me big time. I said no and he was ok with it but he gave me his call number and said I could stop by his apartment anytime. I couldn't stop thinking about it.
A couple of days later I texted him and said yes. I made an excuse with my husband to be late and I followed Tim home after work. I figured it was safe, Tim was a player and not looking for a relationship. One time thing.
It went great at first. Yes I was amazed at the size of his penis, the girls were not lying. It was more than twice the size of my husband. I told Tim a condom was necessary. I was not on birth control. I wasn't trying to get pregnant but we (myself and husband) had an agreement that if it happened we would be ok with it. I remember trying to roll a condom on Tim's cock. It looked like a little hat instead of a condom. We both laughed. When he finally worked all of it inside me I had never felt so full and stretched. Tim fucked me in several positions for at least 30 minutes. At the end he bent me over the side of the bed and just hammered me. Then panic set in. Tim grabbed my hips and shoved it all inside me. I felt the cum hitting my insides. He just leaned over and held me there until he completely finished. When he let me up I was crying and could feel the cum running out of me. Then I saw it. The condom was laying on the floor! Tim had taken it off when he was behind me.
Tim just told me to get over it and go home. Now I am pregnant and don't know what to do.

Nipple Sucking With Pregnant Friend.

ok so this so so weird, and if breastmilk or pregnancy isn't your thing keep moving but...I helped my pregnant friend with her swollen tits by sucking out her milk when she was engorged and in a lot of pain, and while I was doing that she started masturbating and squirted, a lot. extremely awkward experience but it made me hornier than anything ever has.

ok. so. we've always been flirty, so there was a bit of a precedent. but recently she was pregnant and having a hard time. insomnia, pain everywhere, issues with baby daddy, sexual frustration, etc. etc. and we were hanging out and I let her vent about all of it. she was in a lot of pain with her breasts. they were super swollen and engorged, and she was just so stressed out she started crying. she confessed that she'd been trying to squeeze them and get milk out to just relieve the swelling but it wasn't enough and she didn't have a pump and she just needed "everything sucked the fuck out."

I don't know how we got there really. but she lowkey asked me to do it because we're friends and it "wouldn't be weird" because she trusts me. well.

I started by squeezing her nipples, trying to squirt it out. nothing, and it seemed like it hurt her. she said "you might just have to suck honestly." so I did. despite her tits being way bigger than usual and visibly swollen and ready to pop, there really wasn't that much milk. I let most of it dribble down my chin and her stomach and drank a little bit. but also, I was just gentle with her breasts and helped her relieve some pressure and, apparently, some sexual tension.

about ten minutes into this she started moaning a little and said "can you feel how hard my nipples are?" and she took my hand and brought it up to the breast I wasn't sucking at the moment. I started playing with that nipple, just rubbing it really softly and she started moaning more and actually whimpering. then, she put her hand down her pants and started rubbing herself.

obviously this already awkward situation had taken a turn. I started to suck her harder, rub my tongue around her hard nipple in fast circles, switch between nipples, massage her breasts, while she started to vigorously masturbate. she was moaning like crazy, and then squirted. her pants were soaked. she was shaking for minutes afterwards. After she recovered from that she was a little snuggly for a bit, then was just kinda like "uh...sorry. thanks I feel a lot better, hope I didn't make this awkward." I mean it was super awkward but she's a dear, dear friend who's super sexual frustrated (plus I found this really really hot) so I assured her it was okay, platonic hookups are chill.

It was the weirdest sexual situation I have ever been in but it was also really, really hot. Can't stop thinking about it.

Two Is Better Than One

Since the major travel restrictions have been lifted, business travel has slowly picked up around the country. For me, this means client meetings, symposiums and trade shows. I was recently at a trade show and I did the unthinkable. I let two men have me.

I have been married for 12 years. My husband has cheated on me so I, while I am no better of a person, I feel like this was my one free pass.

I met these two black gentlemen at an after event the first night of the trade show. After a couple of hours of talking, they invited me back to one of their rooms. I texted pictures of their trade show passes to my best friend and headed up to their room. The desire, the nerves, the anticipation were all on super high. I wanted this but I never thought I would actually do it.

We got to the room and immediately started. One by one, pieces of clothing piled up on the floor. In short order, I was in a hotel room with two majestically hung black men, both knowing this married white women was down to fuck.

One started kissing me and the other landed his lips on my tit. I grabbed for both cocks….they were so heavy in my hands. Stroked after stroke, kiss and suck after suck, the desire increased. They brought me to the bed. I laid on my back, with one attacking my pussy with his tongue and the other finding my mouth and throat with his dark cock. It did not take long for my hips to start bucking as my first of many cums happened. Fuck…it was so fast. They changed ends and put me on all fours. One put on a condom and found my pussy…..my god did he stretch me…while the other shamelessly fed me his cock.

This back and forth lasted about two hours that night. I came multiple times and they both came twice.

Each of the next two nights, we followed the same steps. We would meet at an after event and find our way to the same room. Each night, they would fill me completely and send me back to my room gaped. Boy, never did I think I would do this, but damn was that a fun week.