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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:

- Dating Disasters -
Straight Female / 75+

Today’s Female’s Are Very Fortunate

In 1957 I was a junior in high school. I didn’t date steady preferring to play the field. I had made the cheerleading squad which made a girl even more popular with the sports guys.

Casual sex wasn’t as excepted back then as it has become today due to the lack of means to prevent getting pregnant. If you did mess around it was with a rubber (what a condom was called back then) or the guy pulled out before cumming in you.

I had managed to avoid having sex mainly due to the fear of getting pregnant but also because once you did guys didn’t keep it a secret they had gotten it.

During basketball season I started seeing one of the players on a more regular basis so we began some heavy making out but still I wouldn’t go all the way.

One night we were parked making out then I got very aroused when he was fingering me.
When he said he had a rubber I gave in losing my virginity.

It was very exciting and pleasurable until the rubber broke just as he came. There was nothing you could do in those days but wait and pray for your period to come.

As my luck would be I got pregnant my very first time. That was a very embarrassing thing getting knocked up back then with no choice but to have the baby.

II had a beautiful baby boy but the guy who got me pregnant never had anything to do with us. His parents paid my medical expenses but I never got any support of any kind from him.

1
# 76465 - by Nancy / January 29, 2025
- True Sex Confessions -
Straight Male / 38

Preforming For An Ex Boyfriend

My wife and I have been married 10 years. She’s now 35 with a body and looks that turns heads whenever we go out. Even more so when we go clubbing. We are both very sexual and we always share fantasies. So the story begins when I finished a work project early. I was supposed to be gone the entire weekend b ended up coming home Friday night. Our TV and Computer room are upstairs O’Shea didn’t hear me coming in. I also got busy trying to get out early that I didn’t get around to telling her I was coming home.

So entering the house I hear her moaning up stairs. Not totally unusual because sometimes she put on a porn flick and masturbates up there when I’m gone. So thinking she’s pleasuring herself I walk up quite like so I enjoy the show before she knows I’m there. To my surprise she’s definitely pleasuring herself using her favorite dildo deeply thrusting her pussy and massaging her tits all in front of her computer. I noticed the computer video camera on and she talking to some guy named Frank. I can hear his voice saying that’s it baby imagine that’s my cock fucking your sweet pussy. I want you to feel my cook deep in that pussy. She moans saying I can feel you in me now. You so hard . I want you to cum in me so bad. I want to feel your cum flowing inside me. Of Frank fuck me . Then he continued on and she would respond back and forth.

My cock was son hard. She looked so sensual pleasuring herself being assisted by Frank. It was about 20 minutes later things picked up with Frank egging her to cum for him. She responded with yes I want to cum for you but first let me see you shoot you cum. I want to see all your cum that will be filling me. Please shoot for me. I need for you to shoot in me. Suddenly I hear Frank grunting and she cried out yes baby that’s it shoot your cum. That so hot baby I want you and your cum in me so bad. Yes baby I’m going to cum baby. I’m going to cum for you. As she thrusted he dildo in her more forcefully she cried out she was cumin . I watched her orgasm for her friend Frank. Her legs shook a little as she came. Then she pulled out her dildo ever so slowly for him. Now exposing her beautiful pussy to him.

At this point I walked in quietly. I was almost on top of her when she noticed me. She was shocked to see me. Quickly standing up in horror. Not to embarrass her too much I said nice show honey. I turn her back around face if the computer. I reach my hands around her. One massaging her tits the other reaching between her legs fingering her wet pussy. Now seeing who is on the computer I recognize him as her ex boyfriend from college. As I’m feeling her off I said Frank thanks for getting Lynn so wet and ready for me. We’re going to sign off . I’m going to going to go fuck my wife.

I turn the computer off. I was so hard and horny that we fucked right there. We later that night talked about what happened and both agreed that it’s always been a fantasy to have her taken by two men that maybe we would invite Frank over for the weekend I he was up for something like that. I really didn’t have time to get mad or anything like that. I was so turned on that I only thought of fucking her.

1
# 76473 - by John / January 29, 2025
- Embarrassing Moments -
Straight Male / 36

Took My Bride To A Nude Beach

I guess I shot myself in the foot - or dick. When we were first married, I was hoping to get my wife to be less inhibited. She was very nervous about being seen naked. I took her to a nude beach (we live near one of the largest). When we were walking to it she gasped when she saw the first nude guy. Her eyes fixed on his penis and she said, "Wow."

We set out a blanket, I stripped naked, and after some encouragement so did she. She sat with her knees together and pulled up to reveal as little as possible.

A guy walked up to us and started talking to her, ignoring me. His limp dick was the longest I've seen, maybe 7 inches, and he was swinging it inches from my face. There was a cool breeze and my penis starkly contrasted, about the size of an acorn. As he talked to my new wife, her breathing became more labored, she lowered her legs and spread them apart. Her pussy was glistening with moisture and her hole was open. Thinking back it's pretty hot, but at the time I was very embarrassed. When the guy got ready to leave, he looked at my penis and smirked.

It's been 5 years since we visited that beach. Every time we fucked after that she seemed distracted and told me that she can't get "those big dicks" out of her mind. She says she prefers what I do with my tongue, and I'm her "good little pussy licker." That's pretty much all I'm allowed to do now.

5
# 76444 - by George / January 28, 2025
- My Spouse -
Straight Male / 27

Jenn's First Times

My wife Jenn and I had been married for two years. Jenn loved sex and she was very responsive in bed. She was multi-orgasmic and very wet. Sometimes we would talk about how I.had fucked another girl and how she had made me cum. Jenn would be very turned on by imagining me in bed with someone else. I also got turned on by thought on Jenn fucking someone else.

Just after we were married, I talked Jenn into sleeping with a friend of ours. I watched as our friend undressed her, played with her great body, and kissed her neck and nipples until she was ready for him. Jenn held my hand as our friend slid into her and fucked her slowly. Jenn responded and fucked him back until he came in her and she had an orgasm. As she had the orgasm, she looked in my eyes and held my erection. As our friend moved over, Jenn put me in her and I added my cum to our friend's. We had two more threesomes with our friend and then went back to monogamy.

Our sex life was still great, and we sometimes talked about our friend fucking her and it would result in heavy sex. By this time, Jenn also enjoyed being tied up and blindfolded while I used a large dildo in her while she sucked my dick. We also started talked about having a foursome with another couple we knew, although Jenn wasn't sure she wanted to do that. Without telling Jenn, I talked with the other couple and they said thy would enjoy being with us. Jenn still did not want to swap when I told her I would like to try it. Finally, I told Jenn the other couple was coming over next weekend and the guy would fuck her and I would fuck his wife. I reminded her of how she had enjoyed our friend in her a couple of years earlier and essentially told her a foursome was going to happen. She said okay.

In bed I watched the guy go down on Jenn and she, without hesitation, sucked his dick. In the meantime the woman had ridden me until we both came. Jenn had watched just as I now watched her. Jenn had two orgasms and the guy came in her. The four of rested on the bed. After a few minutes, I took the woman's hand and pushed it against Jenn's wet pussy. Jenn was startled, but the woman pushed her fingers into Jenn and masturbated Jenn while I kissed Jenn and sucked her nipples. Jenn exploded in an orgasm. It was her first with a woman.

The guy fucked Jenn twice more and I fucked his wife twice more as well. Jenn and I talked about everything the next morning. We now have an informal date with them about every four or five weeks. The guy and I do not have sex, but we swap wives and we get off on watching the women have sex. We'll very likely go back to monogamy for a while after a few more times.

2
# 76446 - by Jake / January 28, 2025
- True Sex Confessions -
Straight Male / 40

Loads Of Cum

1st my wife and I have played with friends before but it’s not a regular thing. She’s very attentive nice slim athletic body with nice average to a little on the big size breast. We have a friend who visits during the summer and stays a week or two. Lina and James are always very sexual with each other. James is a single attractive man in his early 30s.

On his visits things can get crazy with a lot of sexual play. He has fucked her in every room of the house in our pool on our boat in the back seat of the car as I’m driving the 3 of us home from the airport. He’s fucked her at our favorite night club at a strip joint on the beach and so on. Linda loves cum. Especially when it’s in her pussy. She says her biggest turn on is knowing and feeling a guy shooting his cum inside her.

So this brings me to James. James has been my wife’s fuck toy over 5 years. He always shoots the largest amount cum that I’ve only seen on some porn flicks. His cum is a very thick white and sticky that seams to glue itself to Linda’s pussy walls and drips out very slow. The times he pulls out and shoots on her breast or pussy lips I can’t believe the mess it makes. I look at it imagining all the cum he shoots in her. When he shoot on her breast she enjoys using it to massage her breast . I shoot a good load but nothing like him.

I’ve always wondered how does some guy shoot such a huge load and some just a stream or two. It just baffles me. I’m not complaining because Linda loves it and it really turns her on. Some evenings James will shoot at least twice in her and me at least once sometimes twice too. Then she puts on panties and goes to bed trying to keep as much of our cum in her throughout the night. The next morning I enter her still feeling cum deep inside her. A great feeling BTW.

Do any of your wives have a craving for cum and have you guys ever witnessed a guy shooting such huge loads. Or if you shoot huge loads. Do you guys do anything to increase your load volume . James says he doesn’t do anything that he’s always been a big shooter. BTW he’s not overly big. He’s good size and somewhat thick but not a monster cock

6
# 76452 - by Me and Linda / January 28, 2025
- Dating Disasters -
Straight Female / 21

On The Date

At a party with my bf I needed to go out for some air. All of a sudden a black guy came from nowhere, pushed me on to all fours, whipped down my knickers and bred me, It was as quick as that maybe a minute and a half. I felt him cum inside me before pulling out and then he was gone. I haven't told him but time is ticking you see I'm pregnant and life is sacred. I don't know what to do we're both white.

5
# 76295 - by Susan / January 23, 2025
- My Spouse -
Straight Male / 42

Sex After Her Gyno Appointment In The Parking Garage

For whatever reason my wife was crazy horny after her gyno appointment. She told me she had been horny all day and then having her doctor finger in her vagina and butt just made things worse.

On the way back to our vehicle she told me to be prepared to fuck her right there and then.

Got in the back seat of the vehicle. Pull my pants and underwear down to my ankles and I was instantly hard. Her pants and thong were on the car floor as she climbed on top of me. As she sat on my dick she said sorry but I got to use you to get off.

She rode my dick like she hadn’t had it in years. Her very wet pussy was soaking my dick. I could feel the juices running down my balls and my pubes were soaked. She orgasmed fairly quickly and just keep riding

I couldn’t hold back for long and I cummed in her pussy as she kept riding to get her second orgasm.

The aftermath was my dick pubes balls and the seat soaked with pussy juice. And my wife’s pussy leaking my cum.

We got dressed. My underwear then soaked with her juices. And my cum leaking into her thong.

2
# 76297 - by Max / January 23, 2025
- Wet Stories -
Straight Female / 42

Thought I Died And Went To Heaven.

Yesterday I had a luncheon date with our neighbor. She told me to bring my swimsuit. For Christmas they got a hot tub. After lunch we switched into our suits. I noticed she had two tubes about three feet long. And I was like, ok? She opened the lid and turned it on. So, after getting in and finding a nice area to sit down. The water jets were feeling good on the old back. After a few minutes she said here's a tube for you and I have mine. I asked what's the tube for? She then directed the water stream on my camel toe and smiled. Oh my god what a feeling. I then instantly removed my lower swimsuit. And directly and aimed the water on my clit. Few minutes later I looked at our neighbor she had her head tilted back on the side of the tub and moaning. Then I realized where her tube was. I figured let's try it. I penetrated myself with about 6 inches with this tubing. The water flow on the inside of me was amazing. During this event I rubbed my clit and ended up having two orgasms.

1
# 76301 - by Charlene / January 23, 2025
- Women Only -
Straight Female / 22

My Sister And I

Not long ago my sister and I went to a concert at a small music venue. My older sister, Pam, knew one of the musicians and she and I wound up talking with him and another band member after the performance. The band was from out of town and had rooms at a local hotel for the night. After having margaritas with them, they suggested going to their hotel. My sister liked the guy she knew and immediately agreed to go. I didn't say anything at that point. But, as my sister and drove to the hotel, I asked her what she had in mind.

After being quiet for a moment she told me she would probably fuck her friend. She said I should drive on home and she would have her friend drop her off in the morning. That sounded fine with me. We met the guys at their room. It turned out to be a room with two double beds in one bedroom with a small living room with a TV, sofa, and chair. We sat in the living room and talked with them and they had some margaritas sent up. After a while we had a little buzz going. Then Pam surprised me, she took her friend's hand and said she'd like to go to the bedroom.

Pam left the door to the bedroom partially open and soon I could see the two of them were naked and Pam was sucking his dick. I said to the other guy that we should probably close the door, but he said let's watch. As my sister moaned as her friend fucked her hard, I found myself feeling aroused. I had never seen my sister fuck anyone and, for that matter I had never watched any couple fucking before. Literally before I knew it, my clothes were off and I was being fucked on the couch. I heard my sister as she came, and that loud moan made me cum immediately. The guy filled me a few minutes later and I came again. I thought that was all, but I was wrong.

My sister and her friend came out of the bedroom and the guys switched. I looked at her friend's erection and took it in my hand. Her friend was now fucking me from behind. My sister was fucking the other guy and was right next to me on the carpet. Around 4 am, Pam and I drove back to our apartment. Each guy had fucked me twice and Pam had been fucked five times. When we got home, we showered and went to bed. The next morning, over coffee, Pam said she didn't know that would happen and hoped I was okay. I laughed and told her that we must be groupies now. I never saw the one guy again, although my sister did fuck her friend when she viited him in Houston. Being fucked, essentially by two strangers, had been really erotic. I was also turned on by being watched as I was being fucked.

Years later, I told my husband the story. He thought I was incredibly sexy to have fucked two guys with my sister and he took me to bed and fucked me. The story had turned him on.

0
# 76310 - by Janine / January 23, 2025
- True Sex Confessions -
Straight Male / 29

My Best Friend's Wife

When my best friend, Jeff, needed to be out of town for the weekend, he asked me to invite his wife Annie to do something Saturday night so she wouldn't be bored staying at home by herself. Annie is a very pretty, slim and fit, 23 year old woman. Nice body and great personality. I did what Jeff asked and invited Annie to come over and I said I would make dinner for us. She got to my place around six and I poured us a couple glasses of wine. She watched and we talked as I made dinner. We had a good time and went to the living room after dinner. She sat near me on the couch. She seemed a bit nervous. I reached out and touched her arm and asked her if anything was bothering her. She said I need to ask you something.

She told me Jeff had told her he wanted her to sleep with me tonight. I was surprised when she explained Jeff had a fantasy about another man fucking her. Jeff had occasionally said how good Annie was in bed, but had never hinted at me fucking Annie. At that point Annie moved closer and asked me to fuck her.

We went to the. bedroom and Annie undid my pants and took me in her mouth. When I was about to come, I asked what she liked and she wanted me to take her from behind. I did, and I had a tremendous orgasm with her. Jeff was right about Annie in bed. She fucked me twice more that night and we showered together the next morning. In the shower, she sucked me until I came in her mouth. I was still in a semi disbelief that Jeff had sent his wife to sleep with me. But, having Annie had been very erotic. We got dressed and Annie thanked me and told me she had really liked fucking me, and then she went home.

I didn't talk to Jeff about my night with Annie, but the next time I visited Jeff and Annie it was clear that she had told him everything. We all talked for awhile about other things until Jeff got up and took Annie to their bedroom. After a few minutes Jeff came back and said he needed to run some errands and would be gone for a couple of hours. He paused and told me Annie was waiting for me in the bedroom and he left. Sweet Annie was lying naked on the bed. She took my erection in her mouth and made me cum. She swallowed my cum. We rested for a bit before she sucked me again until I was hard. She got on top of me and fucked me so well.

Strangely enough, Jeff has still not spoken directly with me about sharing Annie. But we all know Annie will continue fuck me.when Jeff asks her. When I asked about what Annie tells Jeff, she said she tells him everything and then he fucks her long and hard. She says he gets off knowing I've cum in her and sometimes she leaves the cum in her for him to see. When I asked her how she fels about Jeff wanting her to fuck me, she simply said, I want you in me whenever we have the chance. I don't know how this turn out. After many times with Annie, I would truly miss fucking her if or when Jeff changes his mind. And, if he does, that will be fine. We are still fast friends.

0
# 76313 - by Michael / January 23, 2025
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