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:

It's All In How You Ask, And A Little Help From My Boss, And Voilá!!!

It happened just like this.

I worked in HR onboarding, in a department of women. Around me was accounting, women, and quality control stats, women, most young like me, my boss and the controller fifty. Anyway, women started to get pregnant, pretty soon we had six pregnant women. My 'emptiness' started to get to me.

Hands on pregnant bellies, baby showers, pink and blue, arguments about boys and girls, mothers in law, and my 'belly' was empty. It wasn't hurt, more like an anxiety, the mirror told me the truth. Not you.

I told my boss, she told me it would pass. In a conversation with the big boss she let him know, I had caught the 'fever'. He did what men do, hugged me, kissed my forehead, patted my shoulder, 'you need a 'boy' friend, a girl won't do'.

By then I could not sleep at night. He, my big boss, was everything you want from natural selection, male, masculine, smart, assertive, aggressive, tall, handsome, broad shoulders, and he tended to hug me, and kiss my forehead and ask for a kiss on his cheek. Of all the girls, he babied me the most.

I sat beside him, asked him politely, would he give me a baby? I would need help, but maybe, just maybe, I could make him a son. Fifty fifty, but I was young, so he had more than one fifty percent chance. My direct boss told me I was crazy, what made me think he would entrust me with his baby? A somewhat, no, not somewhat, a lost in space girl. Why didn't I grow up first.

He saw it differently, and in no time at all I was number seven. I did, make a son for him. A bouncing baby boy. He trusted my boss to watch over me. A year later I made a little girl.

I swear, how he approached me was 'mission' centric. I was on the bus, he drove the bus, and miracles do happen. And now I have a thirty month toddler and a six month old baby sister. A mother in law of sorts, and a stern father figure.

My Wife Emilia The Ugly Duckling

I have gone to school with my wife Emilia since we where in grade school. She was never ugly but she was a red headed freckle girl with long hair. Pippy long stockings type. Was never mean to hear but wasn’t really super nice. As we grew up and got into girls around the 7th and 8th grade we dated or where a couple. She had a great sense of humor and she started to get cuter. Not going to lie she had a nice look to her. Still other girls were more developed. High school came and we hardly saw each other. Graduated and never looked back went off to school out of state. Absolutely hated it and came back a year later. Finished up at state which was very close to home and got an apartment and a big boy job. Out with friends and one evening I’m walking back from a bar we had been at and I see this red headed freckle girl with her hair in a pony tail glasses sitting at this diner by herself. She was very pretty very pretty. She was in sweats and a sweatshirt. Sitting having coffee reading a book. Then I realized it was Emilia my old class’s mate. I let my friend go on with out me and I went and said hello. She recognized me we spoke for a while. All the while my where blowing up my phone we sat and talked. She was still the same Funny shy girl. Had gone to state graduated still lived at home. Had friends but they where no where at rowdy as mine. I was absolutely blown away by her. She could have been a square or gained 200 lbs she was absolutely beautiful and we just connected. I spent the evening with her walking her back to her parents house and we kissed that was it. First on we text called each other as we where best friends. I told her that I’ve ate don’t be more then friends and pretty much spilled my guts to her after a few times of going out. She felt the same way and we became a couple. Oh and she has a killer body. Nice big rack a slim waist and an ass. Pale skin and some freckles but gorgeous. Never rushed her into anything we spoke about sex and she asked if I really liked her. I said yes she asked if we where exclusive I was honest and said I hoped so. She just let it go and a few weeks later she spent the night. She was a virgin most she had ever done was a handy and let a guy feel her up. She said she was close with a guy once but caught him cheating and dumped him. So she was always nervous and she was a bit shy. From the first time she spent the night I absolutely knew I never wanted her to leave. More and more she spent more time with me. Her parents where not completely happy she was moving in. It was almost a year and a half of not making it officially. She mentioned that her dad was not super happy. Kind of strong beliefs kind of guy. I totally understood so I went and bought a ring that I could afford at the time. Went out to dinner and while at the same cafe it all started I popped the question and she screamed yes. The best decision I ever made plus she still hot as fuck and after 2 boys she still a little adventurous in the bedroom. Always keep an eye on the ugly duckling is my point

I Wanted To Tell Someone

I'm married, mom of three adult children although my youngest son is in college and still lives with us part time.
I'm a cheater, I have cheated on anniversaries, my husband's birthday, I was pissed at him and gave a young guy his birthday blow job one year. My husband commented the next day that I missed it. Oh sweetie, I'm sorry, you know I love to swallow cum on your birthday. I was so wet as I told him that. I had a fuck bddy for the two years i dated my husband, I fucked my aunts date to our wedding, in my childhood bedroom turned into my dads home office, the night before I was married and sucked a cock in front of my future sister in law the weekend before at my bachelorette party. She will never tell 'cause her married ass got bent over and fucked by the stripper. I did suck him to completion and she denied he was truly inside her. Her moans sounded real; yet, I digress.
I've been bored, so bored, i think I take it out on my husband, not on purpose. In my defence, I let him fuck me before our first date. He was a contactor at one of my dad's sites. He asked me out several times, when I said yes spur of the moment we left the office and he was sweaty and dirty, he asked if he could stop by his hotel and take a shower. When he came out of the shower my panties were laying on the bed. He asked are those yours.... We still laugh about that. Whose did you think they were. Lol I pulled my shorts down to show him my mound and he took that as a sign to eat me. Holy shit, I can't stay on track here.

This week, my best friend's husband has been sniffing around. We had a couples dinner date a few weekends ago, actually labor day weekend. All of us were drinking, they had driven to our house. We left our car at dinner and uber'd back to our place. His wife was out, my husband was out. I pulled my tits out on a dare. I thought that was enough of a first move but he didn't take it. I told him yesterday, "if you want to fuck me, or what, get a famous Kathy blow job. You're going to need to stop by when my husband isn't home." He said, "uh, like tomorrow?" I said yes" like tomorrow. He just left, I was going to just suck him off, after he was fully hard I wanted him to fuck me. It's my friend's fault. She never told me he was hung like a horse. I mean, I thought I saw some bulge in the past, but this guy is a grower. Not just length like most, thick and long.

What Happened In The Caravan Part 2

the guy pulled away and I sat there very conscious of the fact that a man other then my boyfriend had just shot a load in my pussy.

This had never happened before. I stayed silent not knowing if my boyfriend knew or not.

my boyfriend then asked me to lay on the floor and spread my legs. As he got on top of me I just had to tell him that the other guy had cum in me. he said he knew and he would cum in me too. so there I was legs spread on the caravan being fucked with another mans spunk in me.

my boyfriend then nutted as well and the other guy said his goodbyes and left. haven't seen him since. this happened 3 months ago in july. we have briefly spoke about it but nothing serious as yet.

it was an incredible experience although i am not sure I would repeat it.

What Happened In The Caravan Part 1

I was a teen mother and have been with the same man since we were both 14. I have always been faithful but for years I had fantasised about trying two men at once.

Our children are now adults 21 and 19 with the youngest currently at uni. so we decided to have a holiday just the two of us. my boyfriend knows about my fantasy. we spent a week in a caravan park near the coast.

on the third night we were in the entertainment complex at the bar drinking and there was a guy who approached me he was cute so I did flirt a little. My boyfriend seemed to find it funny but as the night went on he suggested inviting the guy to our caravan where my fantasy would come true. I shot that down immediately.

that said when my boyfriend was fucking me later on the thought came back to me I asked him if he would've actually done it and he said yes. we ended up dirty talking with me saying all the things I would've done with them both and that I wish I had done it.

I didn't think much of it the next day we went to the beach went bowling played in the arcades typical holiday stuff. I had considered it to be just dirty talk the previous night and thought no more of it.

That night we ended up in the bar again we watched a magician who wasn't very good and after the show the other guy turned up at the bar.

I mentioned to my boyfriend that he was here and after a while he ended up sitting at our table drinking with us. the guy was going to be leaving the park the next day and my boyfriend pointed out that if I wanted this threesome to happen then it was the last night it could.

i laughed him off at first but then ended up hinting that i wanted it to happen. my boyfriend took the hint and invited the guy back to our caravan for a drink when the bar shut.

we walked back to the caravan and suddenly I felt incredibly nervous, there I was with my boyfriend and this guy sitting in our caravan alone.

I wasn't sure what would happen would my boyfriend actually go through with this? would I?what if the guy isn't interested?

Next thing I know my boyfriend is discussing sex with this guy while I sit silently feeling embarrassment and panic.

Then bam, my boyfriend brought up my fantasy and told the guy that I had never even touched a dick except for his. I didn't know what to say or do and the guy tried to bring me into the conversation, I was speechless. My boyfriend made a joke about my nerves and even told the guy that he had offered me to have them both and we had been talking dirty about what I would do while having sex last night.

my boyfriend then starting making out with me, I didn't dare look at the other guy at this point. Then my boyfriend put his hand in my pants and started fingering me, i said we should do this in front of the guy but they both laughed it off and said not to worry.

At this point I that the threesome was going ahead.

My boyfriend took his dick out and put my hand on it. I looked over at the other guy who was just staring at us I asked if he was ok now that my boyfriend's dick was out and he said yeah and asked if he should get his out. I didn't respond but my boyfriend did, he told him to get it out and come over to the same sofa we were on. I felt a lump in my throat, my nerves were going wild. this was actually happening.

I started sucking my boyfriend and the other guy was standing right next to my face wanking himself. the weird thing is that my nerves started to subside at this point and I just felt horny.

my boyfriend asked if I was going to at least touch the other guy's dick . I jokingly said i was working up to it then i looked my boyfriend in the eye and mouthed the words are you sure?, he nodded so I took our guest's cock in my mouth my boyfriend watched and at points moved my hair out of the way to see more. my boyfriend mentioned that during our session the previous night i had said i wanted to have both cocks in my mouth together. i pulled him closer and starting sucking both of them, it was an odd feeling but it was pleasant.

The night continued and my boyfriend took me from behind while I was still sucking the other guy.

I suddenly felt both of them pull away a bit and I wasn't sure what they were doing, it quickly became apparent though- they were swapping places. I hadn't considered this earlier the other guy was going to actually fuck me. I didn't think it would go so far.

I was frozen to the spot waiting to see what would happen and then just as I looked up at my boyfriend I felt the other guy taking hold of my hips before I could say anything he was in me.

I became incredibly excited at this development and sucked my boyfriends dick as if my life depended on it. In the hurry there had been no mention of a condom and after a few minutes our guest announced he was close to cumming and asked where to do it.

my boyfriend said it was up to him either on my bum or to my shock inside me.
the guy continued until i felt his dick throb and I knew.

I Can Explain The Interracial Puzzle...

I consider myself a normal white female. Married with 2 kids (yes, to a white guy). I think I can explain the fascination with interracial sex, specifically white females and black males.
I grew up in a very rural area and an even smaller school. My high school class had like 60 something people. No blacks in the school at all. Country girl hearing the rumors about black men and the large black penis. I was a cheerleader and with football and basketball games I was exposed to other schools that had black students.
Simply put, I was 16 years old, pretty hot back then, so it was not hard. I was curious and started talking to a few black boys from other schools and towns. Like I said, "not hard". I was curious, and once I made up my mind having sex with black boys was easy. And I admit I enjoyed it. I maintained casual sex with black boys and men up until marriage at age 24.
As for the "giant black penis" rumor. I have to say the majority of black guys I had sex with were above average in cock size. Ran into a few in the small range, but on the other hand also found a couple with HUGE equipment. For me it wasn't about the penis size (although big was good). Black boys and men treated me different than white boys and men. The sex itself was so different, pardon the pun, but "night and day". A way to describe it would be to say white guys wanted to "play" with my toy, black guys wanted to "break it". White boys and men treated me more respectful, sex was more like "love making". It was just different.
The small school I attended closed. My daughter was bussed a long distance to a bigger school with a healthy black population. The time came when she confided in me she was attracted to a black boy. Actually she had past the attracted part and had been having sex with him. We had a nice mom, daughter talk and I disclosed my past with black guys (NOT ALL of course). As you can imagine her father was blindsided by her dating a black boy.
Up until then he didn't know about my past. And I told him everything. Even confessed I had a "goodbye" one night stand with friend just days before our wedding. He was angry but got over it. Since he has asked me many questions about it and even it has cropped up in our sex life. Fantasizing about him seeing me get fucked by a black man. I might just do it!

Freebies

My ex bf once told me I could have a freebie because he had sex with multiple partners before we met. The rules were simple, one day, be safe, and don’t tell unless he asks. I agreed but never thought I would go through with it. Then one day he got drunk and told one of his friends, loudly boasting about how he had sex before I did. A couple of months later, we were to go to a concert with a group but he caught COVID. I was upset I had spent good money on a nice outfit and our tickets. Then one of our friend’s brother decided he would pay for the ticket.


The day of the event Paul’s sister car pools the group and I end up in the back of the suburban with Paul. Everyone is pretty chatty, but Paul begins whispering in my ear and asking if I had used my freebie yet. His hands slip up my thighs making me sooooo turned on. He takes one of my hands and shoves it down his crotch. I play with his balls, they feel so full and hard my vagina starts aching. We find parking and make our way to the event.

At the ticketing area I can’t find my stub, and Paul tells the group he will go with me back to parking to search for it. It’s late and dark so no one thinks anything and agree it’s a good idea. Anxious and frustrated, I’m completely caught off guard when he pulls me under the garage stairwell to tell me he hid his underneath the seat and pulled mine from my purse. We end up kissing against the wall, a woman walks past us and begins complaining when she sees him pulling my skirt up and grabbing my ass.

We make it to the car, Paul bends me over and tells me to look under the seat. I find the ticket and feel his patchy beard and tongue on my bare ass then sliding between my legs. I think I had two orgasms before he entered me, he filled me up, then started ramming me behind the car door. Somehow no one notices us fucking for some time but his sister gives him a call. Still inside of me i can hear him giving excuses claiming I was crying and needed to freshen up when we got back. He hangs up and gets back to ramming me when all of a sudden a security startles us. Her expression was hilarious, she rolls her eyes and tells Paul we need to wrap it up and head down before she makes another pass. She leaves, Paul goes back to fucking me just in time before she comes back around. He shoots a huge load inside of me. The security lady laughs, oh you young couples are so free spirited now. Cmon guys, I’m escorting you down now, can’t have yall up here and get complaints. We end up getting a good laugh out of it, before we exit the garage she pulls a Paul to the side. Hey give this to your girlfriend you animal. I realize it’s tissue paper for the cum running down my leg, I get embarrassed. The security lady gives us space as she looks out for people passing by. I finish cleaning up, she tells us to enjoy the show.

We missed a third of the show but it was so hot. I think about how things could have turned out if it was with someone else, but Paul took control and fucked the hell out of me. I never told my ex bf, and I got to date Paul for a little before he moved out of state.

Thirty Years Later And I Have Never Told Him

Friend of mine is a year or so older than I am and when he went away to college for his freshman year his mom would call me up whenever she needed some help at her house. I went over there one day after she called me saying she needed the light changed in the laundry room, she did not want to get up on a step ladder. I walk in knocking on the door at the same time because that was just what we did at each other house, she walks into the kitchen area wearing just a t-shirt I thought with underwear on under it but no, none. I get the light bulb changed out and then it was well maybe could you change the batteries in the smoke detectors and she is walks off to get some 9V batteries while I go into a room and pull out the old one from one of them. She is talking to me the whole time then when I am up on the step ladder in her bedroom she friggin' kisses the front of my jeans right on my cock and says Hmm, nice bulge you have there! I am trying to install the battery, she has a hold of my hips and is just kissing it over and over laughing and staring at my crotch. She looks up at me with her mouth open and over the head of my cock thru the material, she stops for a second and asks me if this is distracting me, lifts up her shirt showing me her boobs and says How about now? Laughs like crazy and starts literally chewing on my cock thru my jeans, tells me to hurry up and get that battery in so she can suck it. Basically orders me to lay down on her bed, takes off the t-shirt and climbs on top of my legs and undoes my pants jerking them down along with my underwear. she sucks me off swallowing it, my first ever blow job, looks up at me and with this pleading voice asks if I will lick her pussy and ends with this drawn out please and tells me she knows she if a bit fat but please, please will I do it. she will suck my cock anytime I want it done. She rolls over onto her back after I said yes, her huge boobs spreading out to the sides and I start licking it not having a clue what to do but actually having a lot of fun with her. Probably half an hour later with several coaching comments her chubby legs are locked outward and she is screaming out with an orgasm. Oh my God she says, that was amazing, you are a real trooper for doing this, get your cock up here for me again. I am trying not to sit on her, my legs are out around her but like I said, huge boobs and a bit heavy. She does not care, come down here and she props her head up on the pillow some so I do it and she is gasping and breathing hard giving me uh huhs as I fuck her mouth and I feel her hands on my ass cheeks caressing and squeezing them, I cum again and she swallows it all down and just wants to keep sucking more. I am reaching behind me playing with her nipples and she is moving her hips around and has one hand down there masturbating as she sucks on me. We finally stop like half an hour later, I licked to another orgasm and she was just ecstatic about it. She kisses me good bye and tells me she is serious, come by tomorrow anytime and she will give me a blow job, I don't have to do anything to her saying she is fat again. The first month or so I was over at her house often, loved playing around with her and getting blow jobs when my friend came home at the holiday times it was so hard to act normal around her because when he was not looking she would lick her lips staring at me or make blow job motions with her tongue in her cheek. I mean she was just amazing.
So I had sex A LOT with his mom back then and have never told him and I just pray she never told anyone about it either.

Let My Friends Grandfather Do Whatever He Wanted

When I was nineteen my sexual urges were pretty much insatiable, I had a toy collection that would have embarrassed me to no end if my mom would have found it. One day after coming back to my friends house from the beach we hung out on most of the day she said she was going to go shower, her mom had asked us to hang around for a few hours because she had some errands to run. So I was sitting there with the grandfather talking some when my mind just went there, bet he would like to touch me, think he was ninety six at the time. I went over to him and knelt next to his chair putting my breasts right over his arm, he was staring at them and smiling. I told him it was just us go ahead and do what you want and without any hesitation he brought his other hand over and slid my top to the side and caressed my nipples. I knew I only had ten minutes at most, let him caress them for a bit then stood up and took my shorts and bikini bottom off, stepped in front of him and bent over moving myself back as far as I could go, both of his hands started caressing my cheeks then I felt him licking me. I just stayed like that until I heard noise upstairs with her coming out of the bathroom, I stepped forward and got redressed, gave him a kiss on the head and told him until next time my friend. He was nothing but smiles as he put his glasses back on and thanked me for the show. Anytime I could I let him touch me.

I Once Sucked Off A Coach

My daughter was playing softball at the time. And we all know how moms will do anything for their kids

I caught the coach after practice one day. We were talking.

I ended up getting on my knees in a restroom stall and pulled his dick out of his pants to give him a bj. I love to suck so it didn’t bother me

I swallowed his load and he just said okay to what we discussed.

A couple weeks later I sucked him again. Very nice hairy dick he had