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So, this is my first meeting and with a guy after getting on Squirt. com. Actually, it was my first time having sex with a man, period. I was taking some summer classes in college, and I got an email from an older man, 52, who said that he was interested in meeting with me. I was intrigued by his pictures; nice stiff looking cock, hairy, tan, muscular body and very masculine looking. He looked good for his age. I was a little shy at first as I am with many other guys that contact me, but I decided to go ahead and set up a date to meet this time. He told me his name was Tim (His name isn’t really Tim, but we’ll say it is for the sake of the story) and gave me his address. He didn’t live far from my campus, so instead of him picking me up, I could ride my bike to his place.
It was about 6:30pm when I rang Tim’s doorbell. When he opened the door, I was stunned. He was wearing only some athletic shorts showing of his cut body. Now, I’m a white, slender college student, 135 pounds at 5’8”. Compared to me, he looked to be 6’1” with easily 200 pounds of muscle. I felt small compared to him. He looked surprised by seeing me there as well.
“The bedroom is this way,” he said rather anxiously. I told him I was hot from the ride over and asked could I have a quick swim. All the blood seamed to drain from his face (probably went straight to his dick). I didn’t wait for an answer, and took off my T-shirt and dived in. I knew he was turned on at the sight of my near naked body. He sat down on a pool lounge and watched me swim for a bit. I climbed out of the pool and laid down on the lounge next to his. The water formed droplets all over my body as I made myself comfortable. He appeared to be very flustered.
I began to move about on the lounge as if I was in some discomfort. Tim asked if I was all right, but when I told him my shorts were becoming too tight from being wet and could I take them off to dry.
He sat back in his lounge and said that it would be ok if I removed my shorts. After all, the yard was quite private. He suggested that he might change and join me for a dip. He then ran his eyes down to my crotch and motioned that I begin. I asked if he might have something I could put on. At first, he said he didn’t have anything that would fit, but then he seemed to have an idea. He told me to go into the spare room, just to the left of the front door. I should find something in there. We both got up. He went off to get changed and I found my way to the spare room.
I opened the wardrobe door, all I saw were women’s clothes hanging up. Skirts, dresses, shoes and boots. They were all pretty small, which were all about my size. I opened a draw and found some panties and other under garments. I then figured out that Tim wanted me to put on some chick clothing.
As I made my way back to the pool, Tim emerged wearing a robe. He saw me and seemed pleased with my find. He told me the clothes had belonged to his wife. I thought they might have been because I noticed pictures of him and a very attractive woman that looked to be in her 40s; slim, curvy, fair skin, very nice rack, and long dark hair.
His big oily hand took a firm hold of my shaft and began to masturbate me slowly. I arched backwards into him and audibly exhaled. He began to kiss and nibble my neck, and when the hand he had placed on my stomach began to slowly rise up to my chest and thumb my nipples, I was ready to come. As seminal fluid seeped out of my penis, Tim began using it as a lubricant, running his thumb around and over my cock head until my breathing became more of a frustrated panting. He wiped some pre cum off my knob with his middle finger and slid his hand under my bikini and down between my legs. I opened my legs wider as his finger searched out my anus. As he began to probe me, his other hand took a hold of my very hard and welcoming cock shaft. I felt great. I felt like coming.
He asked me to try and bring my knees together. This only served to put more pressure on the base of my penis and balls. His hand took a firmer grip of my cock shaft and he began to work his big hand up and down, stretching my cock magnificently.
He managed to get up off the lounge and stood over me. “My turn” he said in a rather calm voice. I looked up at him towering over me. I began to move toward his rock hard penis. He stopped me and gently pushed me back so that I was lying flat on my back on the lounge. His hands grabbed either side of my bikini and rather roughly pulled them down my legs to my ankles. I asked him what he was up to, but he was busy using the bikini to tie my ankles.
My breathing began to quicken. He must have seen panic in my eyes, because he grabbed my wrists and held them down. As his tongue began to enter my mouth, he released one of my wrists so as to guide his cock into me. I made a muffled noise. This time, he placed a hand over my mouth and began to press his hard shaft further into me. His cock was so thick. Bigger than any of my toys I had trained myself for. His whole weight was focused on his entry of me. He had to because I wouldn’t have been able to take him otherwise. He began to gently thrust back and forth. As he did, he said, “Ahh, yeah, you have a nice pussy. ” Each thrust went in a little deeper and with each thrust, Tim would groan. I would moan loudly over his hand on my mouth on every entry. Slowly but surely, his movement became a little faster and a little deeper until his forward thrusts began to jolt my entire body. He had closed his eyes and started to mumble, “Oh yes.
He opened his eyes and gave me a look of surprise, as if he had forgotten whom he was fucking. He gave me a quick smile and then slowly eased his sagging manhood gently out of me. He removed my ankles from around his head and let them down onto the lounge. I won’t bore you with the pain that was engulfing me except to say that I couldn’t move. He laid down on the lounge adjacent to mine and let out one almighty sigh. “You are a great fuck. I hope I didn’t hurt you too much, but I like it a little rough and I don’t mind the tease you’ve got!”
After we rested a bit, Tim led me to his bedroom.
Tim then grabbed my head with one hand and started to move his hips. It seemed clear to me now that he likes to be in control. In and out of my mouth, I started to enjoy it more. My dick became hard again. He forced his cock deeper into my mouth then I was going before. I was starting to choke a little. He started to pump faster and faster. Finally, he squeezed my head with both hands yelling, “Oh fuck! Ahhh!” and jolted his hip up, shoving his dick to the back of my throat.
After I caught some air, Tim told me to lie down on my back. I did as he told me and he started to mount me like before. This time, however, he let my knees dangle by his sides. He moved up closer with his balls touching mine, and his dick lying on my stomach. He seemed half erect with mine fully hard. His was still bigger! I was really turned on by this. He this took both of our cocks in one hand and began to stroke them together. His hand went up and down our shafts. I just closed my eyes and enjoyed the moment. I could feel his cock getting hard again. I couldn’t believe it. I was preparing for another fuck like before. I told him I didn’t think I could take another hard-fucking like before.
Tim told me to flip over. I turned around and lay on my stomach. He took me by my hips and pulled my up to him. I was on all fours now. He grabbed some more lube out of the nightstand and proceeded to put some on his cock and my ass like before. He then put his hand on my back and shoved me down into the bed while holding my hips with his other hand. I could feel the strength of his muscles forcing me in the position he wanted. Tim took his cock and started to penetrate me again. It went in a little easier this time. He shoved himself all the way in to the point where I could feel his balls touching mine. He then lay down on top of me wrapping his arms undermine grabbing my shoulders with his legs position outside of mine. He started to kiss my neck as he slowly went in and out of my ass.
Tim took he arms and propped himself towering over me, so he could get a view of his cock entering in and out of me. He widened his legs to better mount me and used his lower legs to pin mine down. His soft, slow movement began to turn into him pounding me. Tim’s force became harder more and more, beating my bottom.
Through the pleasure I was enjoying, I managed to tell him to cum inside me again. Tim replied, “You want me to breed your pussy again? Fill your little cunt with cum?” I beg him, “Yes, I want you to fill me up. ” He then said, “Okay, I’ll unload inside you. ” He then stood up on his knees taking his large hands pulling me up by my hips. I was forced to widen my legs now. I still laid flat on the bed as possible as he pulled me up. He then gripped on to my hips and fucked me long and hard. He was pulling almost all the way out and rammed my ass as hard as he could, hammering his balls into mine. I had to grab on to the sheets of the bed to have something to hold on to. Finally, he climaxed and jolted me so hard; he took one hand to put on my shoulder to keep from falling on top of me. I felt his throbbing cock and all of his cum pour into me. He struck me two or three more times shoving his load in as far as he could.
After he was finished, he laid on top of me with his dick still inside me.
Tim got out of the shower, looked at me, and smiled. He asked that I should take a shower too. It sounded like a good idea, so I gathered my strength and went to the bathroom. After the shower, I came out of the bathroom and my clothes were sitting on the bed. I put them on and found Tim in the living room. He said he had a good time today and we should do it again sometime. I defiantly agreed.
Right before I left, he told me that his wife knew that about our meeting. She had left before I came over, so we could be alone. I was a little shocked by after he told me that.
(End)
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