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:

My Wife

The first time I had a "date" with my wife was something else. I invited her to dinner at my place. We had a terrific time. After dinner, we wound up on the living room couch and began to make out. After a time, she was really getting into it, but she stopped me and asked to go to the bedroom. In the bedroom she took off her clothes and stood in front of me so I could look at her. I pulled her to me and she unzipped my pants and took me in her mouth. She was very good. I stopped her, got undressed, and we made love several times that night. It turned out that I was only the second guy she had slept with. The other had been her boyfriend for three years, but she had broken up with him.

As we got to know each other better, I told her I was regularly sleeping with three other women, but she did not care. As long as I also slept with her, she was fine. After a while, I dropped the other women and was just with my wife. It was obvious that my sexual experience vastly exceeded her, so I asked her if she thought about having sex with other guys once in a while. Our discussion continued for several weeks and I finally told her that she should have some fun with other men as long as she could think about it as just recreational sex. During the next four months she slept with four guys. She fucked all of them the first time they went out. An old high school friend stayed with her for a week at her apartment and he fucked her the entire time he was there. She met a musician at a concert one night and had a one night stand with him. She met another guy at a party and slept with him all weekend. Finally, she met a guy who became a long term friend for almost five months and he fucked her probably two hundred times before she called it off because he was getting too serious. So, as I had originally guessed, she loved to fuck and it came as no surprise that she fucked all of these guys the first time they were together.

I was fine with her having some sexual adventures. It was hot to know another guy had been in her. More than once I fucked her with someone else's fresh cum in her. Very erotic. I loved that she liked to fuck. When we were married, it was not long before we had a threesome with an old friend of mine. It was my wife's first threesome and she got off on it. About a six months later, she spent the weekend with him. She told me afterward she behaved like a slut, but knew I was okay with her doing anything she wanted. She continues to sleep with my friend about once a month. When she tells me about it, we have great sex. Knowing my friend has cum in her is very arousing for me.

Wife And Our Friend

A year after we were married, my best friend Jason and I had a threesome with my wife, Amy, that was fun and exciting, but was incomplete. As background, I had asked my friend if he thought about sleeping with my wife. Separately, I had hinted to my wife that she might enjoy sex with Jason. When Jason came to visit Amy went with it and we were all naked in bed with Jason going down on Amy. When Jason finished, I took her from behind. Amy was moaning with pleasure and extremely wet when I came in her. Jason got on top of Amy, but could not stay hard. So, the evening ended with with Amy not having Jason.

Another year went by and Amy and I were visiting the city where Jason lived. I suggested to Jason that he invite Amy over for dinner because I had to be away for a couple of days. I encouraged Amy to accept. She was nervous and excited because she knew what was likely to happen. As for me, I figured Amy would make love with Jason and then come back to the hotel where we were staying. Dinner went well and Amy wound up in bed with Jason. But, she was so aroused by Jason that she spent the night and most of the next day with him. Later she told me he had fucked her several times that night and again in the morning while they showered. After breakfast out, they went back to Jason's place and were in bed until late afternoon. At first, I was really annoyed with Jason for taking advantage of the situation and going way beyond the boundaries. But then, I understood that Amy had made the decision to stay. Knowing that Amy had chosen was very erotic and sexy. She told me she had sucked him and swallowed twice, he had her from behind a couple of times, had fucked her in the ass once, and Amy, who likes being on top, had ridden him a half dozen times. After telling me all of this, we had a great time in bed, although Amy was a bit sore.

Amy really got off on sex with Jason. She said she liked the thrill of another man in her and holding another man's erect penis knowing it would soon be in her. She was fond of Jason, but didn't love him. He was fine fuck buddy. Amy and I have an agreement that she can have Jason whenever she feels like it. The fact that we live in different cities means that she and Jason do not see each other often which is fine with Amy. For the past two years she has been with Jason one or two nights every couple of months or so. The last time, I watched Amy fuck Jason, and I am hoping we will soon set up a threesome. Not for everyone, I know. But, it works for the three of us.

Friend Sleeps With My Girlfriend

My girlfriend, Riley, and I met up with an old friend, Greg, in the city where we lived. Greg was in town on business and had a room at a very upscale hotel. We all went out to dinner and had a great time catching up. Afterward, we caught some music at a local jazz club and then wound up back at Greg's room for a drink. As it was late and we had been. drinking, Greg suggested we spend the night and not try to drive home. Greg and I got in bed with Riley between us. Once the lights were out, in kinky moment, I whispered to Riley that she should give Greg a hand job and I would pretend to be asleep. She reached over to him and touched him, but he rolled over and Riley assumed he wasn't interested. The next morning we woke up, pulled ourselves together and went out to breakfast.

After breakfast, Riley and I went back to our condo. We climbed into bed together to make love. As we were getting into it, Riley said she needed to tell me something as I was fingering her. She said she had been awakened last night when Greg started gently rubbing the inside of her thigh. He then moved to putting his finger in her. Riley said it felt so good that she let him continue. Eventually, after she was wet, Greg pushed into her from behind and made love with her until he orgasmed and came in her. Riley said she had been very responsive and pushed back against Greg,, but was very quiet so as not to wake me. After some time went by, she masturbated Greg until he was hard again and then guided him into her. He filled her again and then they went to sleep.

I was really surprised that I had slept through Riley taking Greg in her. But, as she told the story, it was erotic and arousing for me. Riley, knowing I was hot, got on top of me and gave me a terrific orgasm. Of course, I asked her if she had gotten off with Greg and she said she had. I asked if she would like Greg again and she told me only if I was completely fine with that. Since I had been the one to ask her to try and initiate sex with Greg, I couldn't be upset about what happened, plus it was exciting to know another guy had been in her. Long story short, she sleeps with Greg when the opportunity comes up. Riley and I are getting married in a few months. Greg will be my best man. Riley and I have planned to have Greg sleep with her a couple of hours before the ceremony. When Greg finishes, I plan to have Riley while he watches. Riley has discovered that she likes to be watched, so she is down with the plan. When Riley and I return from our honeymoon, wee'll have Greg over for a threesome. Perhaps strangely, the three of us are into this. Not sure what will happen if Greg gets a serious girlfriend.

Threesome With Brother

When my brother and I were in college we had sex multiple times. The first time we were drunk and I'm not sure he even knew who I was. The second time it didn't seem to matter so much. After that it was just here and there when one or both of us were between partners and feeling horny. It hadn't happened in many years.

My husband found out because my brother was drunk and has a big mouth. My husband thinks it's the hottest thing ever and encouraged us to hook up and let him watch. It's been years since I did anything naughty or kinky. Honestly, the marriage was in a rut. So I agreed to it.

Last night we did it and I'm not sure how I feel. I know it's weird. At first it was awkward getting in the mood with my husband watching. I'd never had anyone watch before. Brother was 100% into it and ready to go, freshly divorced and ready to party with pretty much anyone. Some of his enthusiasm caught on, and we were heavily making out while my husband jerked off in the corner. For a moment or two I almost forgot about him.

Brother got my clothes off, got me onto my back, slid into me and fit inside as perfectly as ever. I remembered then how good he used to make me feel, maybe because what we were doing was so taboo. So yeah, it was hot. It had been a long time since I'd felt like such a naughty sex goddess. Brother gave me what I needed, and I guess I gave him the same. He came inside me since I'm on birth control and I trust him to be clean. My husband came in my throat about ten seconds later while my brother was still panting with his softening dick inside me.

So here I am, thinking about it. I know it's weird and wrong, but that's what makes it fun. I told them I'd do it once just to let my husband have his fantasy but I can't stop thinking about it. I've never had two creampies at the same time and maybe this situation is my chance. I'm in my 40s and it seems like I'm too old for this nonsense. But yeah, it's nice to feel like a sex goddess again for sure, if only for a bit.

Mother And Daughter

My landlord Andy is fifty seven and not in good health right now.
He had an accident climbing onto his roof and fell. So this past eight months, he and his second wife Tania haven't had sex.
She's thirty eight and very sexually active, so he feared she'd find someone and leave him.
That's where I come in, literally.
Andy asked me like he was talking about the weather, if I'd fuck his wife.
At first I thought he was joking, that was until Tania walked into their lounge wearing only a pink ribbon dr**ed across her breasts.
Andy said he'd leave us to it and went to the pub.

When he got back two and half hours later a little drunk, he walked in on us having oral sex. Or to be more precise, he saw his wife sat on my face having yet another orgasm.
We'd fucked in probably every position known to man, and then some during those hours. And even though I pride myself on having stamina, I was utterly knackered.
I'd cum twice and each time Tania had chosen a different hole, her mouth and pussy, she wanted my spunk in after long sessions of fucking her.
All she said to Andy when she'd finished shaking on my tongue was "Hi babe".
And trust me I have been fucking Tania constantly from that night until now (Four months).
She calls by my flat, which I only pay a nominal amount of rent on, two to three times a week. And she has us doing all kinds of sexual things together.

But I'm not just fucking one female in the family. Tania's daughter who's a year younger than me, called round a few weeks ago. She'd brought some paperwork to do with the flat. I invited her in and we got chatting in the kitchen as I made us a coffee. Then out of the blue she asked me if I was fucking her mum.
I was about to lie, but she didn't give me a chance as she leaned over and kissed me.
One thing lead to another and before long I was fucking Tania's daughter from behind as leant on the work surface. And if anything A is far more dirty than her mum.

Both mother and daughter now know about one another, yet there isn't any kind of jealousy between them. They're not the best looking females out there, but both are in great shape and A has a beautiful arsehole I absolutely love fucking.

Last Monday after I'd fucked Tania from behind on my bed and she'd orgasmed on my cock, she asked me if A orgasms like she does. Cheekily I said "Why don't you find out, I'll fuck you both together".
She laughed, but she didn't say no.
And two days later in my car having oral sex with A, I told her what her mum had said and how I'd replied. Her response was "mmmmm" with a mouth full of my cock. Again she didn't say no, and when fucking her on the back seat, she seemed extra horny.

Why Do I Do This?

I am a 42 year old happily married mother of two. My husband and I have a mostly satisfying sex life. We are intimate, erotic, we experiment and role play. Our sex is regular and healthy. But I didn’t even realize I have been missing something important I didn’t even know I needed. I feel incredibly guilty about what I have been doing but I’m obsessed and I can’t stop. Let me explain.

I work part time a few days a week for a non-profit organization. Last December we had our annual holiday party. My husband would have been with me but he was on a rare business trip. The kids wete with my parents overnight.

At the party I spent a fair amount of time chatting with a man I have worked closely with for a couple years. “Ted’s” wife died a few years ago. Admittedly we both drank a bit which influenced our behavior. As we were saying good night Ted sort of broke down and revealed to me how lonely he has been since his wife’s passing. A big part of what he missed was physical intimacy. We ended up granbing a drink and…you guessed it…wound up in his bed. I’ve never done anything like this since being married.

What happened took me completely by surprise. Although Ted was not big in the endowment department (actually slightly smaller than my husband) he was so forceful and sort of primal. His technique was to deliver a non-stop almost brutally hard pounding for an hour. The only breaks were for Ted to move me into a new position and then start the piston-like workout all over again. It sent me to another place, like an out of body experience. I was moaning and saying things that didn’t even make sense and making sounds and moans and sighs and gasps like never before.

I always enjoyed sex with my husband, and before him with two men in college. I usually orgasmed. But my husband is a gentle lovemaker, not a powerful one. It’s just his way, and I never knew otherwise. But Ted’s deep, powerful , rapid and seemingly endless thrusts have become a feeling I’m addicted to. My eyes roll back, I become swollen and dripping wet and I seem to leave my body, and I rarely orgasm fewer tha 4 times in our now weekly 1-hour rendezvous sessions. Loud moaning sometimes screaming orgasms with my nails digging into his back.

We have mindless sex weekly now. Not an affair or a relationship, just sex. Honestly, we just fuck, hard. It’s what we both want and need. I still love and have enjoyable sex with my husband. But I need what Ted gives me. I just do. I can’t unfeel that. I need it. I feel so guilty but I can’t stop.

My Day Off

Took a sick day off work, now I get to watch my 30 year old wife do her stay at home job for a short while. She's been doing it since the scamdemic and she's pretty good at it. She is currently fingering her asshole to the sound of tip chimes. I'm waiting to see her finger blast her pussy after which she usually squirts and then gets off. When she is finished and still messy from squirting on herself I'm going to pound her tight pussy and cum in her asshole.

I Was Born To Be A Housewife

I would never admit to being repressed sexually. I am standoffish, I'm not nurturing or affectionate. I am a good worker.

The company I worked for was suddenly bought out and my position eliminated. I got a months severance, eligible for cobra and then nothing. I had just bought a car and signed a lease on a new apartment. My friend at work, never any involvement, told me to cancel the apartment and I could stay with him until I found another job, as a CPA with over five years experience I should have been hired by Tuesday.

But I never applied for a job. I stopped paying cobra, got behind on my credit cards and my student loan, stayed home and did housekeeping. My friend watched B movies, some with sexual situations and topless girls. Any sexual depiction, any T&A or nudity, any male overpowering a female gave me goosebumps. It was hugely uncomfortable watching. Even Hallmark girls surrendering to the male lead made me uncomfortable. I never watched porn, and he didn't mind some meme with a sexual situation.

I hid behind the kitchen towel and my apron. I spent my days with laundry, cooking and cleaning. One movie night, a shoot'm up with hot girls, he put me on the carpet and asked if I was better with things being 'real'. He hit me up in between my legs where it doesn't hurt, and feels good. I never went on birth control being basically non sexual. Now I was going to be impregnated.

He didn't so much as give me a choice, it was take it or leave it. I could stay home and be a housewife, or get a job and move out and get a job. I chose housewife, which had a pregnancy attached to it. Time moves slow, and fast, one day I was caring for a baby. I didn't know about my credit balances or student loan payments. My car wasn't repoed, I had money for groceries and diapers. On his insurance I was his 'common law' wife.

I take my toddler to mother's day out, I'm 16 weeks pregnant. I'm a full time mother and housewife. And I never want to go back to school or work again.

Wife Did It For The Money

My wife and I were a behind on bills and such and stressing a little but I was up for a promotion at work with a substantial raise. Well I went for my interview and just got a wave of nerves and I bombed it, like flat out knew I messed up when I left my bosses office. I apologized the next day and asked for a reinterview. I was denied which is understandable because they had several over the next couple weeks.

Well I started looking and applying for a 2nd job to just get ahead. I was applying for anything and everything. This went on for a couple days when my wife came up to me while I was online applying. She said don’t get mad at what I’m going to suggest but I could sleep with your boss to try and help you get the job.

Now my wife is 27 and an absolute bombshell. She is way to gorgeous for me but she’s with me for some reason. My boss is 50 and just an average guy. We talked about the pros and cons and eventually decided to go for it. I gave her his number and she went to work. Well some “I’ll do anything to get my husband the promotion” text and a couple nudes later. He was on the hook in less than 2hrs

She met him at his house the next night and slept with him. She arrived home late and I asked her if she had fun. She said I won’t lie I kinda did. I asked for some details because well curiosity got me. She said it was fun because sex is fun but it was nothing special. He was slightly smaller but not much. She gave him head to start and they had sex twice because he came in literal seconds the first time. She told me she didn’t think he got laid much because she could tell he was nervous and he kept thanking her.

Well I got the job and she blocked his number. He walks around with his chest puffed out around me at work cause he doesn’t think I know. At first I felt like a failure but I’ve gotten over that because as she used to remind me she suggested it and went through with it for us.

So call me what you want but we are happy, healthy, in love, and debt free

Fooling Around While My Husband Travels

My husband started a new job right before covid, that would involve a lot of travel. Due to covid, he wasn't actually travelling, but he has been quite a bit the past 2 years finally. Twice a year he has to go on a 2 week trip to Germany. The first time he would be gone that long, he paid a High school boy in our neighborhood to cut the grass once while he was gone. He is a very handsome guy, skinny and has great abs. He was cutting the grass without a shirt on and I just watching him out the windows while having some wine, and may have touched myself a bit. I decided to say hi and went out with some lemonade, and asked how old he was. When he said 18 my heart fluttered. He took the lemonade and I jokingly offered some vodka for it. Ill never forget his tan, fit body while he said "You serious, I mean... yeah." I gave him some vodka, and my number so that we could coordinate if I ever needed him to cut the grass again.

The next weekend I got a text from him and I felt a bit shameful and embarrassed about my behavior, and had sort of forgotten I gave him my number. He was asking me to buy some alcohol for him and his friends. I told my husband I had to go run some errands, he could have cared less. I went out and grabbed the drinks he ordered, and asked if he could meet me at a park near our houses. After this I just felt confused. This guy was so handsome and nice, but what was I hoping to get sneaking around from my husband for a guy who was just out of Highschool. He told me I was so cool but I drove back home still wondering what I was thinking. As I pulled into our garage, I realized I didn't have any groceries and my husband may get suspicious. I guess I wasn't surprised when he hardly noticed me return, and even less so that I didn't have any groceries.

I continued to buy drinks for my neighbor, lets call him Eric. We occasionally had some friendly and flirty texts as well. While Eric was actually giving me some attention my husband continued to go through his motions and ignore me. He made me feel like I lived alone sometimes. One night while my husband was gone, and he had been extra frustrating before he left, Eric had asked if I could grab him some drinks. I told him that he could just come pick them up at my house since I was home alone. I had gotten him the usual beer order, but added a bottle of whiskey as a g*ft. I invited him in and he was very thankful and asked to repay me, but I just asked him to have a drink with me. As we were drinking, I found out he didn't have a girlfriend. I told him how surprised I was, that someone who looked like him could be single. he said "Well someone as beautiful as you probably understands wanting to be single for awhile." I blushed, my heart skipped a beat, and I was more turned on than I had been in the last 5 years. I knew why I had continued to indulge him the past few months at this moment, and I decided to do something I never thought I would... I invited him to the bedroom. I could tell he was excited and he said "I've thought about this happening so many times, Yea I do!" I grabbed his hand and brought him upstairs.

I was wearing a plunge top and no bra. I knew where I wanted to the night to go, and he put my mind at ease with how sweet he was. We got into the bedroom and he sat on the bed but then was still, so I told him to do whatever he wanted to me. His hand easily slip into my top and his hand wrapped around my right boob. I started to kiss him while his hand explored my chest and stomach. I pushed it off my shoulders, fully exposing my top to him and he started to suck my boobs. He was wearing sports shorts and I started to grope his crotch. I started to work my hand into his shorts but he asked me to stop. My heart sank and I felt bad, I stood up and apologized, but to my surprise he said "No I don't want to stop, I just want to take care of you first." My husband hadn't had that mindset since early in us dating. He worked his hand in my pants and asked if he could take them off. I helped him, and he pressed his face between my legs. I hadn't felt a tongue inside me in years either. I could tell he didn't really know what he was doing, but something about that made it feel better in its own way. He went at it for about 20 minutes and he had gotten me close to cumming a couple times, and a full cock would put me over the edge. I got up and grabbed a condom for him, He put it on and I laid on the bed so he could get between my legs. I felt so warm in his arms as he positioned himself on top of me. I ran my hand down his abs and he pressed his cock into me. It felt so good, the way his hands and mouth explored my body, I truly felt desired. He was in me for about 20 seconds and a the familiar quick pulsing from my husband started, but there were 2 differences. Eric came A LOT longer, and as soon as he was done, he kept going. Inviting Eric over has become a regular occurrence over the past year, and he can go 3, sometimes 4 times in a row.