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:

Uncontrollable

Married mom of 2 with both kids at my school. Private school so small classes manageable kids are for the most part good. I instruct 6th grade the teacher across from me Tori or Mr T is what the kids call him. He’s in his early thirties tall really good shape. Dated the science teacher down stairs actually they are off or on. I’m 5 foot 6 155 lbs small boobs but decent sized nipples. Thigh thighs and bubble butt is my claim to fame. There’s 2 get lots of attention jeans legging short skirts even some of the 7th and 8th graders at time make little comments and i over here them. My husband is a very nice guy tall also in great shape outdoors type that likes to spend a lot of time out doors. That’s where we see things differently. While I like to enjoy indoor bathrooms he wants to rough it and I choose to not go. He takes the kids and I spend time with my sister or friends. Now with T he gets me and knows what I like. I have always had kind of wild
Side. I was. It a slut in college but had a few bfs. I enjoyed the larger sized penis and I’m not ashamed to admit i enjoy ass play and a good ass fuck. Another thing my husband does not really enjoy which I’m surprised because he likes my thighs and ass. He will eat my kitten lick suck and all but the tongue finger and cock prefer to go no where near my peach. I’m giving the short version of this so it wasn’t as if I just spread my ass one day. No he flirted chatted asked me to drinks did a lot for me called me his work wife. All while he was seeing the science teacher by the way. Sometimes things happen that you can’t control. The excitement of the moment definitely helped made me feel young again then one day it was after school. School had started we were almost 6 weeks in and we had conferences. 3 days of half days kids in at 8 out at noon. Last conference was at 6 same as Ts. We were the last ones on our side of the building we could hear some voices on the other end. It’s a very old building so it’s of echoes lots of space between rooms. We had been heavily flirting for weeks when he leaned in kissed me and kept kissing me. I was kind of sitting on my desk perfect day to wear a fitted skirt and blouse with heels. Before I knew it I was laying back and he kept saying all he wants was to taste me I wear thongs and g strings always sexy just do it’s what I like. I could feel he tongue in my kitten and it felt good. I’m on my back heels and legs in the air getting tongue lashes when he licks across my puckered ass and i feel his tongue forced into it. I swear he reads minds because I made a whisper and her sucked on it. Never had some one suck on it then force his tongue in as far as he could. Stopped stood me up pulled around and on my tummy. If anyone would have waked in they would have waled in to me on my stomach bent over the desk skirt around my waist thong now around my knees and his tongue eating my pussy and licking up and down and rimming my ass. I’m. Or going to lie I lost control and in a good way. I let that man into my sacred of holes. He made me cum form the vaginal sex I’m talking big leg shaking pissing all over my self and him O. I was relaxed and slumped over my desk when I felt the head. By the way his cock is the biggest I have ever felt but what makes it so special is the over sized head it’s huge almost like a not I feel it rub my walls and i absolutely need that a lot. Never had this happen before. Well when it went into my ass. It rubbed the pussy walk through my ass and with my hand helping my swollen clit. I had a big O with anal always felt like it could happen and now I knew what it took. I went home fucked and used. No guilt just wondering when I could feel this again. We don’t make it obvious but we see a lot of each other I do suck flash him he licks me when we have a chance. We made it where we don’t have a class at the same time. I have to bite a towel to keep quiet. He spends the night intoned the night when the kids and hubby are on one of there camping trip. My bf knows she is the only one and had asked what if u get caught. Honestly not sure of if I could give it up. I pretty much gave in to T going as far as professing my love and giving myself and love to him. He says it back. He says now I know why the science teacher keeps coming back. I know I can’t give it up. I honestly wish I could be with him as I right this. I could use a weekend of getting used.

2 Couples Cross Marriage (true Story)

My ex-girlfriend and I moved to China seven years ago. We’ve always lived and worked there on renewed visas. We weren’t big on parties or socializing much with the expat community, but she did make a close Chinese friend. For two years, their friendship grew, and I wasn’t really involved. Her friend was very different from my ex cute, but with a distinctly Chinese look, while my ex was more European in appearance.

Eventually, we organized a double date at our place. The four of us connected instantly. Everyone spoke English well, and the guy, though a bit younger, was friendly and easy to get along with.

**From Friends to Family**

Over the next three years, we became inseparable. We travelled together summer, winter, spring, and fall from the seaside to the ski slopes, from saunas to ice bathing, and from hiking in Europe to trekking in tropical jungles. We found our forever friends.

Our friendship was anything but typical. There were moments that could be called “spicy” naked saunas, games like spin the bottle, and a lot of physical closeness. They often said they didn’t feel very Chinese in their mentality and appreciated our open-mindedness. We all agreed, silently, that one-on-one bonding was important to strengthen the group. As adults, we were aware of the risks, but after three years, we were all ready to embrace whatever came our way.

**A Turning Point**

One winter evening, after celebrating and drinking, the chemistry between us was undeniable. Her boyfriend’s girlfriend took my ex’s hand and said, “Come on, guys, cut to the chase we can almost see your brains working.” She pushed my ex toward her boyfriend, and before he could ask if she was jealous, she cut him off: “Do you think you’re the only one with dirty thoughts?” Then she sat on my lap.

What followed were months of blurred boundaries, a lot of sex, and a deepening connection. Almost coincidentally, both girls became pregnant around the same time, and it was clear who the fathers were.

**A Solution and a New Normal**

Around this time, our visas were expiring. His girlfriend (my current wife) suggested we cross-marry to solve the issue. We did, and we celebrated the wedding together.

Today, we’re still close friends. We still spend time naked together in saunas, spa and seaside, and physical affection continues across the couple (we don't want to change), though the dynamics have shifted because she is his wife and his gf is my wife and we go home at the end of the evening to our respective children's. It is not always super easy and sometimes jealousy can come up, but we care way too much of each other, and our kids are growing up almost like brothers. Nonetheless, I don't leave you imagining and yes We’ve even had a few nights where all four of us were having sex, it was super weird having sex back to my ex and I was almost jealous, but surprisingly, we all agree that we are more connected to our current partners. We all believe it was destiny.

My Wife Cucks Me

If you have ever set up online fuck dates you know there are no shows and flakes. My wife loves cock, I'm much older than her so 15 years ago we started adding men to our sex life on a regular basis. Craigslist was very easy. I even joined in meeting men by myself without my wife, she didn't even know. As we got more into cuckolding we added more men so she could get the full mfm experience. This is when she first saw the bisexual six of me. I would stroke, lube up their cocks and guide them in to her pussy. Licking her cream filled pussy was something that really turns her on.

When we played out fantasy alone she used me with her strap on, eventually she fucked mein front of her bulls. None of them ever fucked me and that was how she liked it. Behind her back, I was getting fucked from time to time.
This weekend was one of the times we invited a lot of men, they all knew at least one other guy would be fucking my wife with them, but, all 5 showed up. 3 were only interested in fucking my wife but the other 2 switched around with me. I was stroking and suckling their cocks as we watched my wifeput on a show. Air tight many times. A few times she was filled in each hole jacking off the other 2 cocks. I was actually super horny, stroking my cock at one point and this started my wife dirty talking. Look at cucky's little hard cock over there boys.. I bet he cums before any of you.
My wife was getting DPd as she watched me sucking 2 cocks. She looked at me and then the guys I was suckingand said something in expected. Butt fuck him, I grinned wide, and kinda chuckled. I've never asked a guy to butt fuck me. I mean there's really only one option when I as a guy to fuck me.... It's always my butt he goes for.
I pulled out my butt plug and bent over. The guy with the biggest cock in the room gets behind me and easily pushed it in. It felt great but not overwhelming. As I moaned my wife started Cummings. She cums a lot with this type of fun, but this was a squirting moaning good one. Fill me up, fill me up she told the young guy that was pounding away at her juicy pussy and he did. With that she spun around on the bed and I put my face in her crotch. Another guy got behind e and started fucking.... Butt fucking me. My wife came again as I licked and cleaned her. Fill him up, oh fuckmy cock twitched hearing that. The guy, I wasn't even sure shock guy it was started fucking me harder until he pulled my hips back and grunted leaving behind his but deep inside me. My wife and I both got on our knees and started sucking the remaining guys still in the game. 2 of them came on our faces and in my mouth. Kissing my wife the last remaining hard cock put my wife on the bed doggy and fucked her like a jack hammer for at least 20 minutes. My wife begged him to cum then begged him for lube. It all fell on a deaf ear. I was able to get the first guy that fucked me hard again. I sat on his cock reverse cowboy, yes, that's a thing. As he sat in the chair we watched my wife collapse face down on the bed, arms spread, the guy held her ass up until he finally pumped his load into her. I tried to lick her but she was not having it.
She literally put an ice pack on her pussy this morning. Do you need one for your butt she asked me. No ma'am I replied and she just smiled and said we are sluts.

Was This My First Threesome?

Go to my profile below then find "My story" which explains how I went from experimental play to actual sex with my sister to understand this story better.

I was 19 making my sister 15. Nobody was home except us and our large pet male Samoyed called Sam. It was one of those days when we knew that nobody would be home for hours. We had already had sex once, and we were into our second sex session for the day. I had got my sister to hop on top of me and we were fucking facing each other, as in she was on top.

Sam wasn't a small guy and had quite a large cock that was also thick. He was always horny, and often inappropriate with almost anyone in the house. If anybody was silly enough to get on their hands and knees around him, he would be mounting them if they weren't careful. He had no shame either and would masturbate himself in front of whoever, he didn't care who watched. If anyone wanted to jerk him off, he was keen, and we had got him off several times that way. Even with my sisters friends joining in.

So while my sister was on top of me, Sam randomly wanted to join in. He was already hard with his massive cock out, and climbed onto my sisters back and tried to fuck her from behind. She almost screamed and jumped off me while pushing him away. His hips bucking automatically in the air as this happens. Sam! She yelled as I start laughing. I asked what did he do (knowing full well what happened), and she told me that he tried to fuck her and she felt his cock on her bum cheek. I said that she should let him. She said, no way. I said, in your pussy. She said what if he got stuck in there? We had both seen him with his girl and they always get stuck for up to half an hour. I said that we have time and he won't be stuck for long. I told her that it would probably feel feel awesome.

Anyway, she eventually agreed but only if I let Sam fuck fuck my ass first. I had been secretly bi for ages and the only one I trusted to know was whoever was involved, and my sister. So she knew how I liked being fucked up the ass. I told her that if she promised to do it, I would as well, but she has to go first otherwise his cock will be going from my ass to her pussy. Ewww! Was her response. I said, I guess you're first then.

She agreed and next we're discussing how she should do it. She wanted her to fuck her from behind, I wanted to see if he would fuck her in missionary position. I told her it would be less rough with her on her back and I would help guide his cock into her. She agreed so that's what we tried. He wasn't into it, so we both help to get him nice and hard. It wasn't long and he was suddenly interested. She put her pussy to his face and then while laying back, we encourage him on top. It was clumsy and we had several tries before he eventually bucked his hips, thrusting towards her open pussy. He rammed more than half his cock inside her with a jack hammer action, he fuck his big cock in and out of her about 10 times in about 5 seconds before hopping off her. She that was fast, and now it's my turn. I told her no, that she didn't even get fucked properly. I said that he has to get stuck for it to count. There was no argument, just her trying to get him back into her pussy. He got back in another few times, but it was sort of a repeat. She did seem to like it more and said it wasn't hurting like before. She then said that maybe it would work from behind as long as it didn't go up her ass. We put cushions on the floor, got him hard again and she got on her hands and knees, he mounted her and rammed her so hard she screamed in pain, as he got the knot in within about ten fast pumps. It happened so fast that I didn't realise that he was even inside her because he pushed her so far forward. She's practically screaming that it's stuck. I asked if she's sure, she started hitting me. Sam panicked as he hates anyone hitting anyone, so he went to run off, and yanks her to the ground by her pussy. Yelling in pain as they both fall sideways. I told her to just relax and it will be over faster. She told me he was so deep and stretching her pussy. Also that despite it hurting, it felt good and she could feel him throbbing inside her while he was pumping her full of cum. After a couple of minutes she was really enjoying the feeling and began a fucking motion, as she tried to add movement to Sam again. He just laid there almost falling asleep. He did look happy though. After about twenty minutes, his cock began to very slowly come out. Then suddenly his cock almost flew out of her followed by a heap of his cum. My sister was shaking from an intense orgasm he had given her on his way out.
This was probably the most kinky thing I has seen or done still. We both enjoyed it intensely, so it was repeated on other occasions.
It was about an hour later before I started with Sam, but that's going to be another story. Stay tuned...

FOLLOW-UP To: Not Sure What I Can Or How To Handle This

After many replies both positive and negative I wanted to clarify some things.
First and foremost the young man did not r**e me. From his first advances to the final outcome I was a willingly participated.
He was a complete gentleman during the entire encounter right down to asking if it was ok to finish inside me which I emphatically gave him approval.
I have no regrets with my only concern being that I’m not on birth control and the real probability of getting pregnant should I continue to see him. The experience was very enjoyable and exciting not using protection with him so I have no doubt that would continue to be the case. Depending on the morning after pill is a risk because it’s not effective after ovulation.

ORIGINAL POST………
Not Sure What I Can Do Or How To Handle This

Over the summer my son’s college roommate visited us from out of state.
One morning my son was up early while his roommate was still sleeping so I asked him to run to the grocery store for me.
A few minutes after he left his roommate came down to the kitchen. We chatted for a few minutes and it was obvious he was flirting with me. I was confused how to react because I was actually attracted to him but he leaned over kissing me on the cheek. When I didn’t say anything he turn me kissing me on the mouth which quickly resulted in a more passionate kiss. The next thing I knew he lifted me up sitting me on the kitchen table pulled my skirt up and had sex with me.
As soon as he finished I ran to the bathroom and cleaned up. When I returned to the kitchen my son had gotten back so after that we never had time to talk and he went back home. I’m not on birth control but my period came the next morning after he came in me so I didn’t have to get a morning after pill.
Now I have an issue because he called earlier this week wanting to slip in town to see me again. When I told him we probably shouldn’t do that he threatened to tell my husband. I’m afraid if I continue to see him I’ll end up getting pregnant. My husband has had an operation that prevents us from having any more children so that would be a real problem. I’m not sure how to get out of the situation but will probably have to see him until I can figure something out.

Birthday Fun

My wife spent her 30 birthday wearing only a black corset and black thigh hi fishnet stockings at a swingers club. We were newish to swinging but had full swapped. Not my wife's thing because she didn't enjoy seeing me fuck other women. We had soft swapped several times at the club and she admitted she had a few blowjob quickies in a place called the groap room. Single guys hung out in there and my wife went back there with other women when she said she was just going to the restroom. After she told me i would give her a couple minutes and then go poke around she went to the groap room at every chance she could. To my surprise she kissed a lot of men. At the time she wanted a no kissing rule. Which seemed common with the couples we soft swapped with. From the shadows, out of her view i watched her suck every dick that was put in front of her, tits out but kept her shorts on, she always wore very short blue jeans. So short the front pockets had to be cut off. She left them undone and open in a v. You could see her shaved mound. Guys felt her up bent her over but couldn't get access to fuck her. If they tried she moved away from them, several weeks in a row she did this. Then towards the end of the night we would pair up with another couple, a new one each time and soft swap with them.

Not to get too long, but a couple times the other couples were begging to fuck. The first couple my wife said the guy coukd fuck her but she didn't want to see me fuck. They said okay and the wife stroked my cock as we watched her husband fuck my wife. They were in their 50s as her husband grunted his wife sped up her strokes and then finished me off with her mouth. The next time My wife said okay, but we had to do separate rooms. Not to get taken here I stayed in the room with the other woman she was early 20s, my wife and her husband went to find another room. I really enjoyed fucking her, she was a three hole freak great body. We fucked for a long time and she let me cum in her ass. We went to find my wife and her husband and apparently they couldn't find an open room. But we're invited into a room where 2 couples were already playing. I watched 3 men fuck my wife it was a long time before she noticed. The woman i just fucked joined in the fun. She told her hubby she was full. They kissed and he fucked her ass doggy then feeding his cock to my Wife. She not knowing where his dirty cock had been or whose cum it was.

On her birthday she was drinking a little more than usual earlier in the evening. She wondered off and i find her in the groap room. Without anything covering her she fucked many guys as women sucked her tits. When 2 black guys got in line i stepped in. She had told me that was a no go. But when I confronted her she said. Its okay. I don't think I'll suck them tho. Lol

She walked out of that room with her stockings at her ankles and her corset lost forever. I had been getting blow job's from the overflow of women coming out of the groap room. An hour if fucking had happened at that point We walk back to our locker so she could get ti wear. She said "I'm so drunk, i think i fucked a lot of people sweetie". I fingered her and she was used. Guys had came in her, she must have sqirted multiple times. She dodged the STD bullit, for the most part. After she had to get antibiotics for chlamydia we were done with swinging after that.

Not Sure What I Can Do Or How To Handle This

Over the summer my son’s college roommate visited us from out of state.
One morning my son was up early while his roommate was still sleeping so I asked him to run to the grocery store for me.
A few minutes after he left his roommate came down to the kitchen. We chatted for a few minutes and it was obvious he was flirting with me. I was confused how to react because I was actually attracted to him but he leaned over kissing me on the cheek. When I didn’t say anything he turn me kissing me on the mouth which quickly resulted in a more passionate kiss. The next thing I knew he lifted me up sitting me on the kitchen table pulled my skirt up and had sex with me.
As soon as he finished I ran to the bathroom and cleaned up. When I returned to the kitchen my son had gotten back so after that we never had time to talk and he went back home. I’m not on birth control but my period came the next morning after he came in me so I didn’t have to get a morning after pill.
Now I have an issue because he called earlier this week wanting to slip in town to see me again. When I told him we probably shouldn’t do that he threatened to tell my husband. I’m afraid if I continue to see him I’ll end up getting pregnant. My husband has had an operation that prevents us from having any more children so that would be a real problem. I’m not sure how to get out of the situation but will probably have to see him until I can figure something out.

My Wife’s Friend

I overheard my wife and her friend (divorced) sexy and fit talking about some of the guys she’s dated. One guy in particular I remember my wife asking what was it like with David? She said he was good in bed and laughed saying he could really cum a lot!! My wife laughed is that a good thing or bad thing laughing?! She said that’s a good thing if you’re really into it and she said she was. Now I can’t shake it off my mind. She finished by saying she thought it was just because maybe he didn’t have sex as much. But no he was just really a big shooter. It made me feel so excited and i wished I was him because it was one thing sge really loved about him. She is very attractive and knowing she wanted him for that really made me fall hard for her. I think she could get any guy she ever desired but he was older and married. She never mentioned size or stamina it was just something out of the ordinary

Totally Confused

My husband was very self-conscious about the size of his penis. Being 4 inches long and maybe five when hard, he felt like I deserve more. One day we went out for dinner and he decided to invite a friend of his along from college. Darrell was a very dark black man With large muscle muscles, And built like a NFL football play.

Things happened, Darrell went home with us that night and the three of us had sex together. Darrell is not a huge guy 6.5 to 7 inches when hard. But oh my gosh, what a difference it is in me.

Darrell has been with us for three years now. My husband has become a bisexual cuck, Who loves and services Darrell as much as I do.

Here lies the problem. When I say, Darrell has been with us, he lives in our home with us. I have two kids with Darrell and a third on the way. My husband has now decided he wants Darrell to leave and he’s not sure about the mix race babies.

I’m totally confused. I am in complete love with Darrell and my husband and don’t wanna lose either one of them. I don’t know what I would do if I have to make a decision.

Darrell is willing to go to marriage counseling, but my husband is not. I also noticed my husband has been wanting Darrell to spend more nights in his bed with him then sharing him with me.

I’m In A Horrible Predicament

Recently my best friend who is single asked me to go on a trip she had won to the Cayman Islands. Our schedule brought us back the evening before my our family was to leave for our already planned vacation.
The evening before my friend and I were to fly back we went out for dinner and drinks. While we were in the lounge having drinks after dinner two attractive younger black guys asked us to dance. Being married I declined but my friend danced with one of the guys while I chatted with the other one.
As time went by my friend continued to dance then asked me to go to the restroom with her.
She told me the guys wanted to go back to our condo for a while asking if I’d ever been with a black guys. I told her no so she said this was my chance to experience it. Of course I was hesitant because I had never been unfaithful but she finally convinced me to let them go back with us.
On the way back I told her I couldn’t do it because I wasn’t on birth control. She immediately told me she had condoms so that wasn’t a problem.
Once back to the condo she and her guy quickly went to a bedroom. I was about to tell the other guy I couldn’t do anything because I wasn’t on birth control but about that time my friend came back out tossing me a condom.
Reluctantly I went to the other bedroom with the other guy getting undressed and in bed. He was very respectful and before long I was very aroused between his foreplay and the thoughts of cheating.
When the time came I opened the condom then put it on what I had always heard about black guys. I had never had one that went that deep and I immediately had a massive orgasm like none before.
The sex was incredible because of his size then when he pushed deep staying I shoved hard and could feel him throbbing as he finished and I had another amazing orgasm.
He stayed hard for several minutes which I’d never experienced causing me to have yet another orgasm.
When he finally pulled out I could immediately feel something running out of me. I asked him if the condom had broken and he said yes it had when I shoved against him as he was cumming.
I ran to the bathroom and I couldn’t believe how much he had done. I cleaned up best I could after it finally stopped coming out.
We had an early flight the next morning and as soon as I got home we had to get ready to leave the next morning for vacation. I never had an opportunity to get the morning after pill.
My husband and I were intimate a couple of times on vacation then when my period was due a week later it didn’t come. I waited a few days then took a pregnancy test and I am knocked up..
I can’t be positive who got me pregnant but considering how intense the sex was with the guy it’s more than likely it’s his.
I haven’t told my husband I’m pregnant so I’m going to see if I can arrange an abortion without him knowing. I hate having to do that but can’t take a chance on the baby being mixed and having to confess my infidelity.