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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:

- Women Only -
Straight Female / 24

Having Babies Together,

An update from my previous confession. I now have a three month old infant. I am staying at home, at least for a while. The idea of pawning off my baby to some woman I don't know or care to know just turns me off completely. It doesn't escape me that I'm fortunate, her father is well off and can support us.

You might remember that I met him at work and he wanted a relationship. He presented me to his wife at the Christmas party, the same night he got me pregnant. After the party, he brought me up to the room in the hotel and had sex with me in front of his wife, that way there would be no secret. Why she turned the other cheek and accepted me, is something I still don't understand completely.

She babied me all through my pregnancy, went with me to several of my appointments, and she was present when I birthed my baby. She is the one that went out to let him know he had a daughter. She watches the baby for me, but I'm there, she just wants to be around the baby. There isn't any sort of sex thing between us, but fondness for each other has definitely developed. She says now that her insides are calling to her, screaming in the night, for her own baby. Believe me when I met her, that was not something she was ever going to want to do.

She works, mostly from home, so she can spend time with me and the baby. She has this vision, of a man walking with a purse full of seed, and he plants a seed in her garden. So sweet, but she has to let him get in there.

1
# 81791 - by Karina / August 26, 2025
- True Sex Confessions -
Straight Male / 32

Another Wife

Our neighbors Don and Gail have been good friends for years. We have spent many hours together and got to know them very well. They are older than my wife and I and in their early 50's while we are around 20 years younger. Don is quite a take charge guy while his wife Gail is very down to earth. In the last couple years we have gotten even closer to them to the point of being inseparable.

It was my wife who pointed out one day how she and Don finish each other's sentences while Gail and I seem to have a deeper connection as well. I thought about it and recognized that over time the dynamics had shifted and we gravitated to the other spouse when together with no one bothered by it or jealous.

We were at their home one weekend and were playing trivial pursuit. Gail was my partner and my wife was Don's partner in the game. We were all laughing and having fun. We had drank a fair bit of wine and smoked a couple joints so were all a little high. Don made a joke about celebrating their win in the game with a big celebratory kiss. My wife looked at Don and teased him saying go for it big guy. Gail and I looked at each other in curiosity. Don leaned over and kissed my slim red haired wife. The kiss was prolonged and they started making out. Gail leaned over and then kissed me. Her kiss was real passionate and combined with seeing my wife and Don necking got me real hot. I kissed Gail back marveling how sweet and sexy her mouth was. For a long time I had been attracted to Gail and her thick grayish blonde hair and voluptuous build,husky voice and sultry manner. Don and my wife left the room to go to the master bedroom. Gail and I followed them and soon witnessed Don's big strapping body on top of her fucking my wife hard on the bed as she moaned. Gail took my hand after her husband had finished thrusting in my wife and she had her orgasm and led me to another bedroom. She undressed me excitedly and herself pulling me on top of her. My hard cock slipped into her delicious wet pussy and I could not last long. She clung to me until I blew my load in her encouraging me and urging me on. The sex was fantastic if a bit short due to my arousal. We talked in bed for a long time then aroused again I made love to her the second time. This time it was much longer and Gail cried out as she had a shuddering climax which triggered my orgasm. We kissed and cuddled after and fell asleep. In the morning we both went into the kitchen together in our underwear and nonchalant. My wife appeared in one of Gail's black teddy's while Don had a bathrobe on. They smiled at us and Don had his arm around my wife. The line had been crossed and the 4 of us accepted the new arrangement. Gail kissed me openly and Don kissed my wife.

That was several years ago. Weekends since then look very much like the first time we switched partners. They have sex and do Gail and I in different bedrooms. During the week we are back with our regular spouses and the sex is different not as deep or intense but still pleasant. Then on the weekends we show a lot of passion,love and affection to our other spouse. It has made both our marriages more interesting.

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# 81810 - by Symbiotic / August 26, 2025
- Fetishes and Kinky Sex -
Straight Male / 24

First Time For Girlfriend

My girlfriend (21) is pretty open about sex and we have a lot of fun in bed. Friday night I watched her suck our friend's dick and swallow his cum. It was the first time she had done something sexual with a guy other than me. As I watched, I got a very serious erection. As a joke, I had told her she should blow our friend. I really did not think she actually would. But she undid his pants and took his dick out and started sucking. Neither my friend or I tried to stop her. Long story short, it opened a new chapter in our sex life. The three of us are going camping next weekend and our plan is for my girlfriend to sleep with both of us for a couple of days. I am really turned on by knowing I will see her fuck our friend. The anticipation is killing me. She is also excited by the idea of a two day threesome. It obviously will be her first time to fuck another guy or to experience two guys.

5
# 81732 - by Elliott / August 24, 2025
- True Sex Confessions -
Bi-Sexual Female / 32

Me And My Across The Street Neighbor Have Lots Of Fun Together

I live in a small community, a suburb of a bigger city. I am a stay at home homemaker and across the street from me lives Theresa who is also a stay at home homemaker. We both have two kids and the kids are in school. We do not get together to drink, we get together to play girl time and have fun that way.

We met easily because of the kids, we live across the street basically. She likes to have fun with me, and I like having fun with her. It's totally different than husbands and it's a lot more rewarding.

We swear up and down that we have lonely housewife syndrome. But I can tell you when she opens her shirt and releases those puppies, I'm on them, I love them, I must be a titty girl.

3
# 81767 - by Lindsay / August 25, 2025
- Fetishes and Kinky Sex -
Straight Female / 41

Husband Asked For It.

My husband and I are swingers, have been for over 15 years. Unlike most swinger wives I have ran into, I don’t like pussy. Kissing women and fondling tits is fun. I don’t even like to finger pussy, definitely not into putting my face in it.
That led us to me meeting single guys with my husband and the fucked me. I found a regular that I sometimes met alone, we did more than was in our “couple” rules. He fucked me in my ass, never wore a condom. Spanking was on the table and he started telling me when and how I was to let my husband fuck me. It turned me on to the extreme. I was to let him listen when I denied my hubby, not letting him cum, or make him ask for oral and say no. My controlling lover had me doing whatever he wanted. The biggest was timing when my husband would be home, tracking his location. My lover left out the back when my husband was walking in from work. I withheld sex from my husband, at one point 5 weeks. Never had we went that long. My lover fucked me and came inside my pussy, as he was leaving my husband came home, I greeted him at the door naked and pulled him on top of me pushing his face between my legs, I fed him my lovers cum. I was nervous, but so turned on, when my husband slid up my body and I felt his cock slide inside me, the look on his face, he knew something was off. I told him I was playing with my toy and kissed him. The taste of cum, mixed with my flavor made me explode.

My lover wanted me to peg my husband, that wasn’t too much of an effort, my husband loved when I tongued his ass. Then came adding my lover back into our sex life. My husband and I would 69 as my lover fucked me, trapped beneath me my lover pulled the condom off and unloaded on me, not in me, that was still forbidden by my husband. I squirmed and squished his cum on my husband’s face. My husband’s cock stiffened then exploded in my mouth as my lovers cum dripped into his mouth. We had him! Watching my husband take my lovers cock in his mouth was at the time the most erotic thing I had ever experienced. I didn’t feel different about him like I thought, we just shared something at that point. For several weeks my husband and I sucked my lovers cock together.

I was running errands one evening and when I returned home my lovers car was in the driveway, mmmmm, what a wonderful surprise. But as soon as I walked in I knew something was different. I walked toward our bedroom and I heard them doing something sexual, I stopped and dropped my packages when I looked in and saw my lover fucking my husbands ass. My husband was under him missionary, legs spread like a bitch and the were kissing. I was shocked and not turned on by the site. My lover motioned me onto the bed, it wasn’t long before I recognized my lovers moans were leading to his orgasm. He came in my husbands ass and pulled out. My husbands cock was soft, he had obviously already came, his cum smeared into his belly. My lover put his still throbbing cock in my face and guided my head towards it, no please I begged. Open your mouth. That’s all he said. I sucked a cock straight from my husband’s asshole.

It took me awhile to understand what was happening, my husband, with my help was a cuckold. I never put that together. I should not have withheld sex, I think he just needed something. Now he sucks most of the men we meet together. We had a foursome on the July4th holiday and we were both getting fucked at the same time.

5
# 81759 - by Tami / August 25, 2025
- True Sex Confessions -
Straight Male / 35

Friend's Wife

I have known Debba and her husband for years and we are good friends. We have hung out together and we have traveled together. I stopped by to visit the other night and only Debba was home. After we had a beer and talked for bit, she asked me if I would like to fuck her. I would love to fuck her. She is really attractive. I told Debba I would love to fuck her, but I needed to think about it. She responded by saying she was not going anywhere. My wife is pretty open, but I am not sure she would appreciate me fucking our friend. I should have asked Debba, but didn't, so I don't know what her husband would think about her fucking me. I am trying to sort through the maze. Truth is I would like to fuck her, but lots of complications. I think her husband may have prompted her to ask me, but I'm not certain.

4
# 81762 - by Jackson / August 25, 2025
- My Cheating Heart -
Bi-Sexual Female / 32

Finally Pregnant, Most Likely Our Last Child

My husband and I have been married for 14 years. He got me pregnant in high school the asshole. He was in the Airforce and we did our best with me working around the bases, was hard to find work. So, I fucked other men for money. No active service men, just older guys. My husband didn’t know. Most of the guys begged me to fuck without a condom but I only did for a lot more money. I was getting 150-250 depending on the guy and what we did. I lie, one guy paid me 200 a month for “unlimited” access. This really wasn’t what I planned to share. So, back on track.

Because I fucked other men, I was on the BC pill. Plus condoms 95% of the time. I kept telling hubby, no more kids until he got out of the military. He did and we did, at 29 I had our second child. We are both in better jobs now so he wanted one more. I am a slut, just saying truth. But I do not and did not fuck other men when we were trying to get pregnant, after I was pregnant I fucked a bunch of guys. Actually I started working again and had several older men that the farther along I was the more they paid. I got my milk to come in early and business was good. This time I planned better. 6 months pregnant and my calendar is full and so is my pussy.

2
# 81763 - by Kari / August 25, 2025
- True Sex Confessions -
Straight Male / 47

Mail Special Delivery

My wife of 13 years and I have always had a great sex life and we continue to change things up to make it exciting and spicy. We have our toy chest that we continue to add to it so we have many options depending upon what the mood is.

My wife had always been straight up until when she made a comment to me after I ate her that she really enjoys the way she tastes and smells. I surprised her when she came home from work with our Bi-Female server friend from a restaurant that we frequent in our bed waiting for her. That day she realized that she likes pussy too.

In our neighborhood we have the community mailbox with several boxes and the larger one for small packages.

We have lived in our house for seven years and have gotten to know our attractive and very fit female mail carrier that we'll call Amy really well. We always give her a g*ft card for Christmas and my wife crochets so there have been many times that we put a note in our box that we have something for her. She will come to our house and we invite her in to give her the items my wife has made for her. We talk for a few minutes and give her a hug.

Over time we have noticed that there are times that she will ring our doorbell and hand us a package that came for us. We chat for a couple of minutes, give her a hug and she will always have a big smile. The items are always the sex toys we ordered. The packages are something that could be put in the mailbox but she will hand deliver them. The companies always ship with with discrete return addresses so she must know what they are. She probably orders form the same places which we both found exciting.

A few weeks later Amy rang our doorbell and had a package for us and asked if she could use our bathroom and we said sure. She did her thing and before she left, she handed my wife a g*ft card and said to open it. She said I hope that this isn't weird but I know that you both will get good use of it while blushing.

The g*ft card was for one of the places we order toys from. We hugged her this time it was closer and longer than it had been in the past. After she left, we both smiled and were very turned on by it so we went upstairs and made love. If we were honest with ourselves we were both probably thinking about her.

A few months later I came home from work and my wife showed me an envelope that was from Amy. She waited to open it so we could read it together. Amy wrote that she was turned on by both of us and would like to get to know us personally is we were interested.

We talked about it and decided to leave her a note that we were but we both had to be involved.

The next day Amy rang our doorbell and we arranged a day and time at our place.

Amy showed up dressed in her postal outfit with her top opened with a pushup bra showing nice cleavage and her postal shorts with her tanned muscular legs. My wife had on a short skirt with a thong and her pushup bra. I had on my golf shorts and a polo.

We sat and drank a margarita with my wife and Amy on the loveseat and me on the couch. Amy leaned over and gave my wife a very passionate kiss which my my wife received well. I suggested that we go upstairs to continue to have fun.

As soon as we went into the bedroom Amy started kissing my wife and feeling her boobs and my wife did the same, and I was so turned on watching them my dick got hard. they climbed in bed and started to undress each other and once they did, they explored each other. They were using their hands, mouths and many toys we had out for this. Amy went down on my wife sucking and flicking her clit with her tongue and had two fingers inside her and I could see her juices flowing down from her pussy to her ass. Amy didn't let my wife cum right away because she wanted her to eat her pussy and cum in my wife's mouth. Amy was more soaking wet than my wife was which was such a turn on.

Amy pushed my wife down and sucked on her nipples and fingered her, then she slid a 7" dildo into her pussy for a couple of minutes and right before she came, she moved back down and ate her until she came with such intensity.

I was watching them and was so turned on and I didn't want to cum yet because wanted to wait and have fun with them.

I got naked and and climbed into bed with them. My wife told me that I needed to enjoy Amy as she did and wanted to watch. I stated kissing her tasting which I tasted my wife, sucking on her nipples and fingering her very wet pussy while she was playing with my balls and cock. I was so hard and getting close to exploding Amy said to face fuck her which I was happy to do. I came down her throat which seemed like it never ended, and she made sure to get every drop.

Amy grabbed my cock and started stroking it to get aroused again. I bent Amy over the edge of the bed and fucked her doggy style while she ate my wife We both came pretty quickly. I flipped Amy over and my wife ate her pussy with my cum dripping out of her.

This was the best mail delivery that we ever had!!

2
# 81733 - by TB / August 24, 2025
- True Sex Confessions -
Straight Female / 23

Open Minded Boyfriend

I was a senior in college and had a steady boyfriend whom I had been with since our junior year. I was pretty prudish until I went off to college. I discovered sex with an older guy when he fucked me for my first time my sophomore year It was also my first orgasm. I opened up (no pun) to another guy when I started my junior year. We were basically just friends, but one night after drinking, I slept with him. I really did not want him as a boyfriend, but I liked him, and I liked fucking him. We would sleep together for the next six months. It was casual and it was safe with him. And, it felt good.

It was during the spring semester when I met my boyfriend. We hit it off really well and before long were lovers. I was also still sleeping now and again with my friend. After a time I started feeling guilty and one night I told my boyfriend that I was still fucked my friend. I expected my boyfriend might dump me, but instead he asked me to tell about my friend, how long I had been fucking him, and if I enjoyed it. I was honest with him, told him it was just casual sex, but thought this would be the end of things. Instead he told me it sounded sexy and we made love.

I could hardly believe it when my boyfriend told me he did not mind if I kept on with my friend. He did insist on knowing when I fucked my friend and what I did to make him cum. He said it excited him to think of me fucking another guy, but was okay with it because it was just a friend, not a serious relationship like ours. My boyfriend was incredibly open minded with me.

After we graduated we got married, moved for jobs, and fucking my friend ended. I had not anticipated it, but the earlier arrangement that let me continue with my friend resulted in my now husband telling me, a year after we married, that he wanted me to start fucking a friend of ours because he missed the excitement of knowing I was being fucked by someone else. I guess I had not realized how turned on he was by me fucking another guy. Gradually a situation was created for our friend to sleep with me. Now, usually every Thursday evening he comes over and we sleep together and my husband stays away for several hours. It's still casual sex for me, a turn on for my husband, and a pleasurable time for our friend because I am good in bed. I've been shared for over a year. I like fucking our friend.

8
# 81736 - by Jessica / August 24, 2025
- My Cheating Heart -
Straight Female / 20

Former Crush

I told my boyfriend that a former high crush had let me know he would be in town and wanted to know if we could get together. My boyfriend was my first lover, so he knew I had not slept with this guy. Plus, my boyfriend was a pretty secure person. So, it was not a big surprise when he told me I should meet the guy if I wanted and catch up with each other. What did surprise me was when he told me to also have some fun if I wanted. He said he had once had a hard crush on a high school girl and still wondered what it might have been like to sleep with her, and he could imagine I might possibly feel the same way.

Given what my boyfriend had said, I became nervous about meeting up with the guy. I had not wondered before, but my boyfriend got me to wondering about what it might feel like. Anyway, I met him at a local restaurant and had a nice time. Lots of good memories. It was when dinner was over and he invited me back to his hotel that I had to face up to the possibilities. My first reaction was to say I needed to be going, but with some coaxing I went with him. I spent the night. He knew how to get me ready and when he pushed his penis into me I had an orgasm immediately. He fucked me two times that night and in the morning I gave him a blow job and swallowed his cum. We showered and had breakfast, then went back to the room and fucked again. Afterward, I told him I had wondered what it would be like to fuck him. He said he had always wanted to fuck me. He asked me what my boyfriend would think about me having sex with another guy and I repeated what my boyfriend had told me. We had a nice goodbye and I left.

Later that afternoon, at my boyfriend's place, he asked me how it had gone. I asked him if he wanted to know all of it. He said he did, regardless of what I had done, and I told him everything. He held me and took me to the bedroom and we made love. He came in me when I asked him to fill me. He told me he was glad I had the experience and that it was good for me. I agreed that it had been very sensual to have my friend fuck me. I thanked him for letting me sleep with another guy. He smiled and said we will need to see that its not the last time with someone else. I asked what he meant. He said I now knew that it was a pleasure to fuck someone different and that it did not affect our relationship which gave me some freedom to explore with his support.

Two weeks later I looked in the eyes of a mutual friend of ours as he came in me for the second time and I had an orgasm as he did. Moments later I looked into my boyfriends eyes as he entered me and we made love. This new way of understanding sex had happened so quickly for me. I had been monogamous with my boyfriend for nearly two years and then, in two weeks, two other men had fucked me. And, with my boyfriend's support and encouragement. I know there will be some more in the future.

9
# 81741 - by Ginny / August 24, 2025
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