Story Details

First Time (Older with younger)

krhodges8 on Gay Stories

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. He invited me in and looked out the door nervously before closing it behind me. He gestured that I follow him. As we walked through the living room, I saw he had a pool in the back yard. I stopped following him and headed straight for the pool.

 

 

“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. Normally, I wouldn’t have done it, but I was in to moment with my heart beating, running through thoughts in my mind. I quickly rifled through the other drawers and found what looked like a bikini bottom. I peeled off my shorts, to some relief, and slipped on the bikini bottoms. WOW. It felt exhilarating to have some strange woman’s clothes barely covering my ass and dick. I checked myself out using a wall mirror. I was glad that I had shaved my entire body, chest, legs, ass and all. I felt pretty good. I closed my eyes and ran my hands over myself. I quickly found some socks and a short denim mini and put them on. All the clothes had a scent or perfume about them that was very feminine. I suddenly remembered Tim, so I jettisoned the mini and socks and kept the bikini bottoms

 

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. I resumed my position on the lounge and pulled the bikini sides up over my hips. I felt really turned on. Tim noticed my bulging cock and reminded me that I may need some sunscreen. He held up a bottle of sun tan lotion and patted the front of his lounge. I got up and sat on the end of his lounge. He moved up behind me, with one leg either side of me. I glanced over my shoulder and saw that his robe had separated. He was naked underneath and a little bit hairy. He opened the bottle of cream and began to slowly rub the oil onto my back and shoulders. He had very large hands. I felt rather small. His legs began to close tighter and I could feel the end of his penis touch the base of my spine. His hands worked their way down my back and began to move around my waist. With each forward massage, his fingers went closer to the area of my pubic bone. My cock was hard now and seemed to strain toward his ever-nearing fingers. As his hands began to touch the top of my bikini, I placed my hands behind my head and started to slowly contort my body with the movement of his hands. I then began moving my bottom up hard against his groin. I lowered my arms and ran my hands over his legs. His hands ceased massaging me and with one hand on my stomach, his other hand gently lifted the bikini over my cock

 

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. His finger stoked my anus and every now and then he would penetrate me. My penis reached plateau. I gave a cry of pleasure and told him I was going to cum. Finally, as I felt the over powering sensation of orgasm engulfs me, I turned to Tim, and I arched my back, and spurted cum all over my stomach and his hand. My body jerked as I thrust my penis in his powerful hand. He began to wipe the cum over my body with his spare hand. He gently but firmly squeezed the last of it out of me and then took his hands away. I let out a deep breath and shook a little.

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. I nervously laughed a bit and asked him again what he was doing. He raised my feet up and put his head through my legs. My ankles were now resting on his shoulders. I continued to smile at him and again asked what he was up to. Tim began to kiss and lick my ankle. He began to move toward me, keeping his lips on my leg and as he did, I had to bring my knees up closer to my head. He forced my knees up so close to my face that I could nearly lick them. My ass was completely open and exposed. He poured a lot of lube in his hand and rubbed it on his cock and my ass. He would shove two fingers in to make sure I was nice and slippery. As he began to position his knees either side of me, I felt the head of his cock touch my hole. He ran his tongue down the side of my knee and then he gently touched my lips with his. I felt his breath enter my mouth. I whispered to him that I hadn’t done this before. He placed a finger gently over my lips and told me to shush.

 

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. That’s it. Oh you’re so incredibly tight. Oh, such a tight little tease cunt, yes. Oh fuck, you’re so tight! Your cherry is mine. Your pussy belongs to me.” Perspiration began to form on his forehead. He was fucking me like I was a rag doll. As his pelvis started to slap my butt cheeks, I felt his cock harden even more. He was really grunting now, and as he arched his back slightly, he grabbed the base of my legs for more leverage. His thrusts were hard and violent. He moved his hands to my waist and squeezed me for more and more thrust. He was using my hipbones as fuck handles. My limp dick was flying all over the place. I felt his cock reach full plateau, and as it began to spasm in me, shots of cum entered my young body. I yelled out in pain and pleasure. He continued to push into me, straining to thrust out the last drop of cum. He seemed to go on forever. Thrust after thrust and he was panting so hard I thought he might have a heart attack.

 

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. He went into the bathroom to wash off his dick and then lied down on the bed. I stood there staring at his muscular body with his hands behind the head and his limp cock lying on his stomach. Even with it limp, it was still huge. I couldn’t believe I had just been fucked by it. I knew what he wanted now. I climbed on to the bed and took his dick into my hand. I began to stroke it and lick the head. I then put it into my mouth. I could feel it beginning to stiffen up in my mouth. It was so warm it felt like it would melt in my mouth. I looked up at Tim as I started to bob my head up and down moving my tongue all around his shaft sucking his head when I came up. It didn’t take long to become fully erect again.

 

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. He let out all his cum and wouldn’t let go of my head until he was done. I was forced to swallow it all.

 

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. He said, “I will be gentle this time. We’ll take it nice and slow.” I was glad to hear that, but even still, after the last session we had, I was still a little nervous.

 

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. I moaned in pleasure, “Uhh... uhh.,.” He whispered in my ear, “After that last fuck, your pussy is still tight. I love your little cunt. You like my big cock nestling inside you?” All I could get out was a murmur. I was so turned on by that comment I felt like I was ready to cum. I arched my back to shove my ass up a little as he fucked me slowly so I could move my hips with his. Soon, our movements began to get faster.

 

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. I finally let out my load just by him fucking me. I almost went limp.

 

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. I could feel it getting soft. After about five minutes of rest, Tim got up and went into the bathroom to take a shower. I, however, was motionless on his bed. I didn’t want to move. I was spent.

 

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. He asked if I would be interested in having a three-way with his wife sometime. Being that I am more partial to women than men sexually and the fact that his wife reminded me of Demi Moore, I couldn’t pass up an opportunity like that. I was a very excited about it. Couldn’t wait until we set a date for that.

 

(End)

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