Quick background: my girlfriend is my age but due to covid we were separated as she is away for school and I am still living at home. Both my parents work healthcare so once our classes ended I had alot of free time. We tried Skype sessions a couple of times but they didn’t do much for her. We are still together to this day but I need to get this off my chest.
So, I went down the slippery slope of masturbating on flingster. At first I would click and click hoping to be paired with a female. It never really happened. I’ve never considered myself gay or even curious, but recent events have really changed my perspective. The first time I gave in and showed my cock was so hot. I loved the thrill of helping a stranger get off, and when they complimented my dick and told me they wanted to fuck me it would get me so hard. I eventually started talking dirty to them, and before I knew it I was wearing pink shirts, and trying to look like a twink. It was becoming a secret obsession. This started in late April.
My girlfriend had a few items of clothing in an old bag in my closet, and one day I put them on. Just a tight red nightdress that cut off around my thighs, and some glittery tight mesh stockings. The response that it got was overwhelming. A few guys would quickly disconnect when they realized it was a man in drag, but everyone else wanted to see more. They would ask me to spread my ass, spit on my cock, and talk dirty to them. I was loving it. I would ask them if they wanted to fuck me, and just hearing the words come out of my own mouth got me so hard. Still trying to convince myself that I am 100 percent straight was getting pretty difficult at this point. I would edge myself closer and closer, teasing sometimes 10 different guys per morning, untill I couldn’t take it anymore and I would treat them to a cumshot. I immediately felt shame after it was over.
By the end of May I had ordered a ribbed silicone dildo on amazon, and the morning it arrived I was ecstatic. I’d never experienced anything going in my ass but I wanted to. I’d been reading up on the prostate and I really wanted to try it. So I did my routine, talking dirty to a random cock without a face about my virgin ass and my new toy. I had even set up my webcam on the curtain rod above my bed to give them a good view, cutting off where the pillow goes to not show my face of course. I had even shaved my crotch, ass and thighs, with very little thought as to what my girlfriend would think when she comes home for the summer.
When I lubed up the dildo and turned around the guy was telling me he wanted to fuck my smooth ass. I was rock hard grinding the bed and awkwardly sliding the dildo around my taint. He told me to stick it in. I slowly worked the tip into my hole and it felt so strange. Not enjoyable. I decided to turn around so I could jerk off at the same time. Slowly I became more comfortable and I had the thing about halfway in and it felt incredible. I looked over at my laptop and the guy was jerking off furiously, not talking. I wanted to switch partners but I couldn’t reach the mouse and I was enjoying myself too much. I shut my eyes and began fucking myself with the new toy.
When I opened my eyes my partner’s cam was just a blank screen. This happens often, shy or creepy people not wanting to show thier face. But the location was my state.
A little perturbed obviously, I took the dildo out of my ass and slid over so I could connect to someone else. Then I noticed the chat. He asked are you in *my city. Without hesitation I said yes.
Suddenly, his webcam clicked on. I was looking at a fully clothed man in his mid forties maybe, bald, but not bad looking. The fact that I thought he was attractive made me blush.
He then told me my legs are gorgeous. I told him thanks, and asked if he wanted to fuck me.
Where do you live? He asked me. Shit. This was getting real.
I told him I couldn’t just invite someone over, and suggested we do his place, to which he replied that his wife is home.
I rolled over onto my back, and started teasing the dildo down my ass crack. He then whispered into the mic. “Have you ever been with a guy?”
“No” I replied. “But I want to”.
“Let me come over.” He said.
I was overwhelmed with urges I couldn’t control. I rolled over and started jerking off.
“Let me see your cock” I told him. He typed into the chat. ‘tell me your #’ … I blurted out my phone number. I almost came right then and there. He then disconnected from the chat.
I instantly regretted it. I just have some creep my phone number! I suddenly wasn’t in the mood. The next random cock was jerking off watching me. I wanted to take off the stupid tights and just jerk off to some regular, straight porn. I missed my girlfriend.
Then the phone rang. I didn’t answer.
It rang again later that evening. I also didn’t answer.
The next morning I was horny again, and I was thinking about the dildo, but I didn’t want to jerk off online any more. I lubed it up and started inserting it. Then I got a text. It was a dick pic from the mystery man.
The idea of hooking up with the handsome middle aged man overwhelmed me.
“Do you have a car?” I asked him.
“Yes, can you dress up for me ;)”
This drove me wild. I asked him if I could call him and he said he would call in 15 minutes. It was official. I wanted this. I was so close to blowing my load at the thought of it. I took a shower. Then I went back to my girlfriend’s bag and began rummaging. I found lipstick and eyeliner and began dolling myself up. I looked completely passable save for my short hair, Adams apple and no tits.
The phone rang and we had a very brief chat. Nothing sexy, just directions to my house and him making sure I wasn’t a minor. Turns out he only lives 30 minutes away. I went downstairs to the living room to wait. After what seemed like an eternity a car drove slowly by my house and parked down the street. It was him. He nervously walked up my driveway, cautiously looking around. I ran to the door to let him in, making sure to hide behind the door so the neighbors wouldn’t see.
He stepped inside and I shut the door and locked it. I leaned against the door in disbelief. He looked like your average straight guy you might see at the gym. Sort of an older version of myself before whatever phase this was consumed me.
“Hi” I said to him.
“Hey” he said back, he was so nervous he was almost literally shaking. He was staring down at my legs.
“Have YOU ever done this before?” I asked him, to which he shook his head. I had never been so turned on. I was going to have to make the first move.
I stepped towards him and took his hand. It was so clammy. I placed it on my thigh and his mouth just hung open. He started slowly caressing my thigh.
“That’s it” I told him, and slowly pulled the dress up to reveal my cock, which was not hard at this point. I was too nervous. His hand slowly worked up my leg as I put my arms around his shoulders. He gasped and I kissed his lips.
It was the most passionate kiss I’ve ever had. Hands down. He began running his hand down my cock which was now rock hard. I pulled away and took his hand off my cock and held it in my hand and led him upstairs. Without a word we went into my bedroom. I laid down on the bed, and when I turned around he was already talking off his pants. He climbed onto the bed and on top of me. We were passionatly making out. I began to give him a handjob and I was blown away at how badly I wanted this. I asked him if I could suck it and he nodded his head. I crawled out from underneath him and put my hands on his shoulders, he took my cue and rolled onto his back. I kissed his neck and told him how hot he was and worked my way down.
I put his cock up to my lips and let it slide in. I could barely get a few inches in before I started gagging. I began to work the shaft, and just as I was starting to get really self conscious he began lovingly stroking my hair.
“just like that beautiful”
I sucked on him like that for maybe 2 minutes, before I took him out of my mouth and began making out with him again. I enjoyed the act of giving him a blowjob, but I didn’t feel like I was very good at it. I wanted him to start working on me.
“I want you to fuck me now” I whispered into his ear, and began to tug at his t shirt. He sat up and took the shirt off. I reached over to the nightstand for the lube, and as I did he grabbed my ass. My face instantly got hot. I wanted him to use me. I rolled over onto my back and pulled the dress up to my chest. I squirted the lube onto my finger and began lubing up my hole.
He put his hands on my chest, and almost too hard began pushing my breasts together. I gently grabbed his hand and guided it onto his throbbing cock.
He awkwardly tried to penetrate me, but I was to tense. I reached over to the nightstand and grabbed the dildo. “Loosen me up” I coyly told him, and he began to slowly insert the dildo into me. He began to work it faster and it felt amazing. Before I knew it was begging him to fuck me. He took it out and quickly thrust himself into me. It was startling and kind of hurt.
Thankfully he started off really slow. I was breathing so heavily I whispered to him to go faster. He began to thrust faster, and before I knew it I could feel the beginning tingles of an orgasm and he wasn’t even touching my dick! I began to moan like a little bitch and I was loving it. “I’m gonna come” I was quivering. He began furiously pounding. In pure ecstasy I listened to the sound of the springs squeaking and the lube shloshing around inside of me. All of a sudden my whole body was numb and hot. It felt like everytime I’ve ever come all at once. It was incredible. I came all over his stomach, hot loads were dripping off his face and onto my chest. I looked him right in the eye and smiled at him. He kept pounding me for maybe another minute and he came. As his O face was beginning to show I put my arms around his waist and grabbed his ass. I could feel all his load fill me up. When he pulled out he climbed off me and sat at the edge of the bed, putting his hands over his face.
“So you’re married?” I asked him. He just nodded. Not looking at me.
“Yeah I hear you. I have a girlfriend.” I got up and sat beside him. I didn’t feel the same shame I felt jerking off online. I kissed him on the cheek and told him he could use the shower. He said thanks and walked to the bathroom. I opened his wallet and looked at his licence. Afterall, he knows where I live, I should know his name at least.
I took off my girlfriend’s clothes and slid them under the bed. I knew I had laundry to do. I was still rock hard. I went to the bathroom where he was showering with the door open. I hopped in the shower with him and began to scrub the makeup off my face. We smiled at each other and I went to kiss him. He we briefly made out but he stopped me. “We’d better not. I’m supposed to be at Costco.” We both had a laugh at this. “Well we’d better be fast then.” And I knelt down and began sucking his cock. He told me he really had to go, so I called him by his first name and asked if we could keep our dirty little secret.
He was taken aback that I had looked at his licence and I explained that I didn’t want him showing up at my house as I live with my folks. He was very understanding. He told me he was going to delete my texts but promised to send me a burner email address where we could chat. We both agreed that we wanted to see each other again, but we have to be very careful. I love my girlfriend and he loves his wife. But we also agreed that was easily the best sex we’ve ever had.
My girlfriend ended up coming home a few weeks ago and we are talking about moving in together. All her clothes are washed and back in the bag, I think she forgot it’s still in my closet. I haven’t worked up the courage to ask her to use the dildo on me yet, but I will. She did kinda comment about how I shaved but I told her I wanted to suprise her. She didn’t seem to care all that much.
I emailed my secret lover last week and we are planning an afternoon getaway in a hotel. He has been sending me links to lingerie that he has already purchased for me on amazon. We are going to make this an ongoing thing. Hope this gets someone as hot and bothered as I am.
Source: reddit.com/r/gonewildstories/comments/hlj0tg/i_m_19_let_an_online_stranger_m_40_fuck_me_while
This will end in tears.