Straight Male / 47
Turn the way back machine to the late '80s.
My first girlfriend, a short, Portuguese brunette, small a cup, tight in all the right places.
Once we were dating, I would swing by her house and take her to college on my bike.
Once classes settled in, I would arrive late enough, so her house was empty. Then we would fuck like there was no tomorrow.
That girl, Anna, would take pipe like no tomorrow, and of course, being 17, it was all fuck, blow load, new condom, insert again and repeat.
In between fumbling with her tits or fucking her from behind, her screaming out how good it felt. Legs over head, 69, cowgirl, gallons of cum a week.....
Then one day, I asked for the Holy Grail. "I wanted to try Anal with her." Of course, not wanting to deny me she said "okay".
Now me being unprepared, I went to her parents bathroom, and in the medicine cabinet was a large jar of Vaseline (with no top I remember).
With shaky hand I reached in and coated my rock hard cock with the stuff, and walked back to her bedroom.
She got on all fours and I spread her cheeks, after a few attempts the head of my cock was pressing against her tight asshole. I pushed in, and got that (my now favourite feeling) of her asshole slipping over the head of my cock and quickly tightening over the shaft. I swear sometimes you even get that soft "pop" sound.
She makes uncomfortable noices, and without even asking how she is doing, my shaft is sliding deeper into her shit pipe. My hips are moving, my cock sliding in deeper, nice full strokes.
Then I start on the long strokes, and pop out, "shit" I think to myself, she's let out that surprise yelp and sigh of relief, that quickly turns into a yelp of pain as I clumsily shove my throbbing cock into her reddening back door. The smell of Vasoline and ass fills the room, she's now in ass up head down position. Mouth full of bedsheet pillow on death grip of both hands.
My cock is balls deep in her asshole, there's vasoline on my pubic hair. She's just taking each stroke with a huge gasp of breath, i marvel at the tightness, so unlike pussy, that snug fleshy ring feeling around my shaft, the greasy feel, as my strokes go in and out.... shit! My cock slips out again, she gasps in pain/relief that it's over.
I hear the dismay in her breath, as I aim and plug her sore hole yet again. Up to this point, all our sex had been with a condom, this was the first time I have had sex bareback, it feels fucking great. I can cum in this hole as much as I want to and don't have to worry about pregnancies!
My balls grow heavy, my shaft starts throbbing, "ughhhh" I yell, as I pump load after load of cum into her asshole. She moans/yells, trying to please me, her asshole is undoubtedly on fire, stretched by my thick cock. Of course I lay on her now, forcing her down on her bed. I bite her hair, my cock slowly pulsing dibble after dribble of cum into her asshole. She's moaning in pleasure/pain, I'm still in her, enjoying ever last second of tightness on my cock, I pull out, and I'm amazed my cock is still rock hard. Ah to be seventeen.
The sent of fresh ass, Vaseline, and cum fill the air. I was seriously worried that we wouldn't be able to get it out of her room!
We went to college after that, she having to sit upon her busted ass cherry, on a bike, me smelling of vasoline & ass every time I took a piss, with a slight grin on my face knowing that anytime I wanted her asshole, that jar of Vasoline was in the bathroom.
I got to say, she took it like a champ.
She went a bit crazy when we broke up, maybe that was because she wasn't receiving her weekly anal cum injections....
My first girlfriend, a short, Portuguese brunette, small a cup, tight in all the right places.
Once we were dating, I would swing by her house and take her to college on my bike.
Once classes settled in, I would arrive late enough, so her house was empty. Then we would fuck like there was no tomorrow.
That girl, Anna, would take pipe like no tomorrow, and of course, being 17, it was all fuck, blow load, new condom, insert again and repeat.
In between fumbling with her tits or fucking her from behind, her screaming out how good it felt. Legs over head, 69, cowgirl, gallons of cum a week.....
Then one day, I asked for the Holy Grail. "I wanted to try Anal with her." Of course, not wanting to deny me she said "okay".
Now me being unprepared, I went to her parents bathroom, and in the medicine cabinet was a large jar of Vaseline (with no top I remember).
With shaky hand I reached in and coated my rock hard cock with the stuff, and walked back to her bedroom.
She got on all fours and I spread her cheeks, after a few attempts the head of my cock was pressing against her tight asshole. I pushed in, and got that (my now favourite feeling) of her asshole slipping over the head of my cock and quickly tightening over the shaft. I swear sometimes you even get that soft "pop" sound.
She makes uncomfortable noices, and without even asking how she is doing, my shaft is sliding deeper into her shit pipe. My hips are moving, my cock sliding in deeper, nice full strokes.
Then I start on the long strokes, and pop out, "shit" I think to myself, she's let out that surprise yelp and sigh of relief, that quickly turns into a yelp of pain as I clumsily shove my throbbing cock into her reddening back door. The smell of Vasoline and ass fills the room, she's now in ass up head down position. Mouth full of bedsheet pillow on death grip of both hands.
My cock is balls deep in her asshole, there's vasoline on my pubic hair. She's just taking each stroke with a huge gasp of breath, i marvel at the tightness, so unlike pussy, that snug fleshy ring feeling around my shaft, the greasy feel, as my strokes go in and out.... shit! My cock slips out again, she gasps in pain/relief that it's over.
I hear the dismay in her breath, as I aim and plug her sore hole yet again. Up to this point, all our sex had been with a condom, this was the first time I have had sex bareback, it feels fucking great. I can cum in this hole as much as I want to and don't have to worry about pregnancies!
My balls grow heavy, my shaft starts throbbing, "ughhhh" I yell, as I pump load after load of cum into her asshole. She moans/yells, trying to please me, her asshole is undoubtedly on fire, stretched by my thick cock. Of course I lay on her now, forcing her down on her bed. I bite her hair, my cock slowly pulsing dibble after dribble of cum into her asshole. She's moaning in pleasure/pain, I'm still in her, enjoying ever last second of tightness on my cock, I pull out, and I'm amazed my cock is still rock hard. Ah to be seventeen.
The sent of fresh ass, Vaseline, and cum fill the air. I was seriously worried that we wouldn't be able to get it out of her room!
We went to college after that, she having to sit upon her busted ass cherry, on a bike, me smelling of vasoline & ass every time I took a piss, with a slight grin on my face knowing that anytime I wanted her asshole, that jar of Vasoline was in the bathroom.
I got to say, she took it like a champ.
She went a bit crazy when we broke up, maybe that was because she wasn't receiving her weekly anal cum injections....
