Straight Male / 29
First Threesome Gone Wrong
My girlfriend (24) of 5 years now introduced the idea of a threesome. Long story short, she had mentioned it was something that she always felt curious about and wanted to try. She was only open to it if I was comfortable. After some thought from both sides, we agreed we wanted to try both FFM and FMM once each. The rules were that I must wear a condom whenever I’m inside the other girl and the other guy has to wear a condom inside her, the third person is someone we both need to agree on and feel comfortable involving, we have to be 100% sure of no STDs from the third person, everyone knows the safe word, and no kissing or making out with the third person (teasing and oral is ok).
My girlfriend within a few days introduced me to her 19F coworker I’ll call Arie who was interested that she knew was interested. After a couple meet ups and hanging out we both decided to go for it for our FFM experience. My girlfriend is bi so she gave Arie oral while I was behind her in doggy. When it came time to switch, I put the condom on and slid into Arie. She was so petite and I could tell was amazing through the condom. We were in missionary while my girlfriend sat on her face. She said she was cumming and started to convulse and get extremely tight. The amazing feeling and excitement made me cum as hard as I could. I pulled out to see the condom ripped and a river of my cum was spilling out of her. They were both upset but understood it was an accident. We got a plan B and that was the end of it.
Now for the real confession. I knew the condom ripped. I put it on right and it came straight from the unopened box. No idea how it ripped. However, I absolutely knew it when it happened because I felt a wetness take over my cock starting at the head and working its way down with every thrust. I could feel her walls and every detail of her. It made me fuck her as hard as I could. When she started cumming, she was so hot, wet, tight, and sexy that I consciously chose to not just cum but to actively push and cum as hard as I possibly could. I’m starting to feel bad but at the same time, she was a truly amazing fuck
My girlfriend within a few days introduced me to her 19F coworker I’ll call Arie who was interested that she knew was interested. After a couple meet ups and hanging out we both decided to go for it for our FFM experience. My girlfriend is bi so she gave Arie oral while I was behind her in doggy. When it came time to switch, I put the condom on and slid into Arie. She was so petite and I could tell was amazing through the condom. We were in missionary while my girlfriend sat on her face. She said she was cumming and started to convulse and get extremely tight. The amazing feeling and excitement made me cum as hard as I could. I pulled out to see the condom ripped and a river of my cum was spilling out of her. They were both upset but understood it was an accident. We got a plan B and that was the end of it.
Now for the real confession. I knew the condom ripped. I put it on right and it came straight from the unopened box. No idea how it ripped. However, I absolutely knew it when it happened because I felt a wetness take over my cock starting at the head and working its way down with every thrust. I could feel her walls and every detail of her. It made me fuck her as hard as I could. When she started cumming, she was so hot, wet, tight, and sexy that I consciously chose to not just cum but to actively push and cum as hard as I possibly could. I’m starting to feel bad but at the same time, she was a truly amazing fuck
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