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:

Antics With My Old Neighbour

Although many years have since passed by I recall with some fond memories the time I was breast feeding my young son. I was then in my early 30’s and it was during the summer months of 1984.

My husband (now passed) was frequently working away sometimes overseas and I was quite lonely if not a little sexually frustrated.

Our neighbour was a lovely gentle man called Jim in his late 60’s. His wife had sadly passed away a few years previously so I guessed he was quite lonely too. Nothing ever sexual had ever crossed mind with Jim so what happened wasn’t planned or even imagined.

Jim was a real treasure doing any odd jobs I needed about the house in my husband’s absence. One afternoon I was breast feeding my son when Jim called by after I asked him if he’d kindly mow the garden lawn. I remember standing in front of him quite unashamedly with my breast out as I continued feeding as my son suckled on me. I let him in and told him to sit down whilst I carried on. My son greedily guzzled away blissfully as Jim no doubt took for stock of the sight in front of him. Sometimes you can’t explain why things happen but as we talked I found myself getting quite aroused watching old Jim’s expression.

After my son had finished gorging on my now very swollen teat I readjusted my breast back into my dress briefly letting him see my naked breast. He continued to ogle my breasts and appeared quite agitated licking his lips. I half heartily apologised for allowing him to see me but he responded by saying it was a beautiful sight. He then confessed that his late wife allowed him the enjoyment of feeding him many years ago.

I placed my son in his cot and returning to the living room I told Jim to come and sit next to me. I said something like” would you like a go then Jim” or words to that effect? After a very slight awkward pause and an enthusiastic nod of his head (he was speechless) I motioned for him to put his head on my lap releasing one of milk laden breasts. He started to slowly grope and gently maul my breast rubbing his fingers over my now erect rubbery teats. This obviously stimulated my milk and it started to flow so I cupped his head and placing a cushion underneath brought his mouth onto my teat. I couldn’t recall how long he sucked away but it was heavenly and he was clearly enjoying this moment as was I as I started feeling quite damp in-between my thighs. I noticed that he’d grown stiff in his trousers and was fiddling around with it. It was quite tense and I brushed his hand away replacing it with mine as I squeezed his erection tightly over the material of his trousers. He must have climaxed soon after as his breathing got intense and I felt his hardness drop away.

Over the next few weeks until my husband arrived home Jim enjoyed his daily feed and afterwards I let things go a bit further when he started rubbing my pussy. I did feel guilty about it but it was something that filled a need as my hormones were through the roof at times. It was during a lengthy period when my husband was away that I was climbing the walls feeling so horny that I succumbed and we ended up in the spare bedroom. That was the first of many trips upstairs to that bedroom whilst hubby was away and I think poor Jim spent a small fortune on condoms. For a man of Jim’s age I was impressed with his stamina that equally matched my husband’s who was much younger.

Everyone Saw

We went to my in laws for thanksgiving this year. My husband always likes for me to dress a little slutty and I enjoy it. I wore a short skirt blouse and heels i looked nice but had no panties on. I kept flashing my husband through out the day. While I have a nice ass and legs my tits are what people gravitate to. I have gotten them squeezed and felt up a lot on my life. Some wanted some unexpected but felt up. We started drinking a bit we where all outside my husband was right by the door waking in facing the inside. There was probably 15 people around him I had gone in to grab some more drinks. My husband kept asking me to flash him and I had ignored him for a while. The booze got to me I had taken off my heels and had on sandals that were a flat. Some one had spilled something that I had not seen. I had given in and shown my husband my boobs and when I went to put my tit away the material on my blouse scrunched up and I could not put my tit away. I was walking and had a drink when I got it put away I stepped right out onto the area where a drink was spilled. My sandals had very little grip and when I stepped my foot went right form underneath me and I slipped I dropped my drink went to grab onto a post all that did was make me spin around and fall back over a out door coffee table. I fell onto my back every once is watching me no one says anything I’m on my back legs spread eagle every one starring at my crotch. No panties a hart shaped bush. My husband’s uncle says wow know we know why she was the one good job nephew. Bursts of laughter my husband is beat red I’m beat red. I was nick named the Thanksgiving day flasher. I was so fucking embarrassed.

What I Think About When My Husband Fucks Me

I can't orgasm from physical sensation alone. I need to fantasize. My main fantasy is that I am being spanked or whipped in front of people. They can be strangers or people I know, and they comment on my arousal. It makes me cum every time.

The Rent Man Cometh

This happened to my wife and I nearly 30 years ago. We lived in rented accommodation with a young baby aged 12 months. We were struggling with the weekly rent and despite assurances we’d catch up the landlord threatened us with eviction. Our landlord was in his late 50's and he always looked at her in a lecherous way. It was because of this we came up with desperate option to trade the rent for some 'physical attention' from my wife. With some degree of reluctance my wife agreed the next time he approached us my wife would speak to him alone and discuss the rent. We decided that if he showed any interest an alternative was for my wife to have sex with him.

We were not sure about what the boundaries were but we discussed her seeing him weekly when I was out at work and our baby was sleeping. It was not convenient for her to leave the flat (upstairs from his residence). As the baby was asleep in his cot in our bedroom so any sexual deeds took place in our lounge area.

My wife could not (for medical reasons) take the birth pill however she had a coil fitted. If he wanted to wear a condom then we’d not object. We agreed that she could have sexual intercourse (with or without a condom) with him and if he was insistent of oral sex (and there were no hygiene issues) she would suck him off.

We agreed that my wife would not tell him I was aware of this arrangement. It was to be their secret. We agreed on a set day to ask him and my wife decided to wear something sexy to create an atmosphere where he was aroused. Weirdly she thought a man of his age might appreciate it if she wore nylon stockings and suspenders with high heels. It must have worked because he fucked her on the very day they met up. It was rather crude as she describes it.

This arrangement last for nearly 8 months during which time he took his pleasures with my wife many times. She later described his stamina was incredible for a man his age. On those occasions when the monthly curse visited her she would suck him off taking his full load down her throat. When we moved away we had with a very healthy looking savings account.

Holiday Sex

Do you have sex even if you’re staying at your parents or in-laws on the holidays?

My husband was really horny while staying at my parents house Wednesday night. He wanted to have sex but for whatever reason I felt it would be too weird to do. So I just gave him a bj instead before we went to sleep.

But Thursday evening after everyone left I said fuck it and let him fuck me in my bedroom there. I told him he has to be very quiet.

Knowing that we could get caught and feeling very naughty having sex in my parents house with them home was just oddly turning me on.

Then going back downstairs with my husbands cum leaking into my panties the rest of the night around my parents had me feeling really hot .

How does everyone else feel about holiday sex?

Celebrating Our 15th Anniversary

My wife and i recently celebrated our 20th anniversary and went out to dinner just us leaving the kids at home. 2 wonderful boys she has given me. What people my family her family our kids don’t know is how Chris and I got together. We met while out on dates. She was with her fiancée and I was with a girl that I was with for sex. Chris is a gorgeous brunette wears glasses. Has that slutty librarian look going short hair to her shoulders. I pair of Double D tits a slim waist and a nice fat ass. My self and other people have told her that she could easily do porn. I approached her while her fiancé was out smoking a cigarette and left her at the table for 5 minutes. I swooped in gave her my number a kiss on the cheek and she was surprised and what she later told me was impressed with my confidence. She took a few days to think it over got into an argument with him on those days and she called me up and asked if i was serious about drinks. A couple of hours later we are at a bar and a couple of hours later after leaving the bar I have her on my floor giving her rug burns on her lower back from the pounding i gave her. She let me get close with her and even though her wedding was being planned she had other ideas. She was so nervous to end it she didn’t really know how to let him down. The closer it got the more sex we where having. She often disappeared for hours ghosting him until we finished i always finished inside her no rubbers where ever used. She liked going home full and said she liked the feeling of it running out down her leg. She often say there and as it leaked she would use her fingers to wipe it off then eat it. This always got me hot and we would fuck again. It was obvious she wanted to end it with her husband to be. So I took it upon myself to send him a letter back then that how you remained anonymous. I basically told him that your future wife has been getting fucked in this particular parking lot after her workout. Because I wrote the letter I told him what time she would be there I labeled it a concerned friend. I just made sure that Chris would be butt ass naked. I took my time ate her out usually she would leave her panties and shirt on. Nope I had her on all 4s ramming her when the door to her old table flung open and he looked in. The sight he was was me behind her I was in her ass he tits where swaying back and forth form the thrust. She sat up tits out line on her ass he of all things started to cry. I got dressed she got dressed. I left them there and a few hours later she came back to me and said it was over she needed a place to stay. A year later she has a ring on her finger. We blink and almost 20 years go by and she still has no idea I sent the letter. Best thing I ever did

Friends Sister Growing Up

When I was about 17 my buddy’s sister was hot as hell and had a bit of a crush on me. One afternoon I went walked over to his place to see if he was home and only his sister answered the door saying he wasn’t home so I was going to be on my way. She asked if I wanted to come in anyways and play video games for a bit so I thought sure why not. We go downstairs and I go to the tv to get it ready. She comes down in a hoodie and track pants no big deal. We play the game for a while and she says this is boring. I asked if she wanted to do something else or I could go home I didn’t really care. She said she wanted me to stay so I did so I was like so what now? Movie? I asked she nah and took her hoodie off. I was like holy shit tits this is awesome but was concerned someone what find out. She said don’t worry that she wouldn’t tell anyone. She then took her pants off bending over in front of me showing me her pussy and asshole. I was rock hard and she started feeling my dick. I whipped my pants down right away and she sucked it right away. She sucked me for only about a minute or 2 and told me to tell her when I was going to cum. I got to that point and she pulled it out of her mouth and put it on her own face. It was incredibly hot and I absolutely covered her face. She rubbed my sick all over and went to take a shower. I left and we both acted like nothing happened when we saw each other again a couple days later. Super fucking hot!

Don't Start What You Can't Handle

My asshole is still dripping with cum.
My husband invited a few friends around last night to watch the game.
Just before half time he got extremely horny and began playing with my pussy having had me sit on his lap.

He didn't try to hide what he was doing and once I got turned on, I didn't care either.
Before I knew it I had my legs spread and one of my husband's friends was tonguing my clit.
And it just went from there.

We all pretty much missed the second half as each one of the three men, as well as my husband, took turns to lick my pussy and ass, and fuck my love holes.
I'm not sure if my husband meant for it to go as far as it did, but believe me I wasn't complaining when each of his friends fucked me.
None of them had a particularly large cock, but the constant fucking and hearing my husband encouraging them to fuck me as he filmed on his phone, had me orgasming over and over.

Two of the men left to go home after a couple of hours, but Rick stayed the night. And he and my husband enjoyed me in bed together.
Again I don't know if it was planned, but I got to witness my husband sucking on Ricks cock in between him fucking my mouth, pussy and asshole.
Rick left here about an hour ago as the sun broke through the clouds, but not before we had sex alone on the rear porch.
And it's his cum that's oozing out of my asshole.

This is an exert taken from my online diary a few weeks ago. Since that evening I've had sex apart from my husband. The man I'm now having an affair with, is someone I met only a few days after my husband encouraged his friends to gang bang me.

In a bizarre twist when he finally woke up with Rick having already left, my husband blamed me for encouraging his friends to fuck me.
I didn't bother arguing knowing the truth of it.

So when an ex colleague, one who i knew wanted to get into my panties, and I spotted each other at the mall, I asked him if he was with anyone. When he asked why, I told him I was looking to have sex.
We drove to a place he knew where we had unbelievably awesome sex on the back seat of his car.
I let him have me anyway he wanted and any hole.
It was though I was paying my husband back for trying to blame Mr. In my mind I was thinking, if he thinks of me like that, then I might as well be damned for actually enjoying myself cheating on him.

My ex colleague and I have gone on to have sex three to four times a week since and I don't plan on stopping, even if my husband finds out.
He started the ball rolling. I'm just taking it into the end zone.

Sex With Friends

When I was 16 I went skinny dipping with my then gf and her three friends, we were all but naked they were all in the pool already and I stripped naked in front of them all I remember I had such a big hard on. I wouldn’t say I have a massive dick but it’s about 7 inches long and fairly thick. I just remember them all just staring at my dick and smiling.after swimming and messing around for a while. My gf and her one friend were getting handsy with my dick. My gf started to make out with me and her one friend went under the water and started to blow me . I was fingering my GF and then her friend would come up and my gf would go down on me and I would finger get friend.band they kept taking turns in ended up coming in my gf friends mouth. After that we went up to my girlfriend’s room together and I end up fucking both of them. I then ended up cumming in her friends mouth again . After a few month me and my GF broke up but I ended up fucking her friend for a couple of years after that. She was such a slut for cum. I never thought my gf at the time knew we were still fucking

Fucked My Friends Wife After A Bulls Game.

I had a friend win tickets to a chicago bulls game. His wife didnt want to go so he invited me and it was alot of fun. We both got HAMMERED at the game, We took a train back to his place, he live about 10 minutes off one of the stations headed out of the city. On the train he was telling me how he wanted to spit roast his wife, and how him and one of his other friends used to spit roast her before his other friend got married. I was dating a girl at the time, but I was also hammered and boarderline blackout. I remember us talking about it loudly on the train, I remember another group of people over hearing us on the train and laughing about it, and my next memory is looking down at my friends wife's tatood back while I railed her doggy as she sucked her husband. I have no idea where, or even if I came that night, and snuck out when I woke up at about 5 am. Im pretty sure I was still hammered when I woke up.