Meg And I Went For A Walk And Then
- 3 years ago
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Tamed By Meg (male Submissive, Pegging) free porn video
It's funny how sometimes you look at something in life and think, I could never do that. "I could never be a surfer..." or "I could never travel alone in Africa..." And then somewhere down the road, you find yourself actually doing exactly that thing. I've always enjoyed sex and sexual experimentation, but I never thought of myself as particularly "kinky". At least until I met Meg.
I met Megan ("Meg") while I was teaching at a local university. She was the T.A. for another class in my department, and had similar interests, so we hit it off right away. She was about 5'6" and had long, dark hair and pretty green eyes. She was pretty athletic, but had enough weight to fill out a nice "C-cup" and size 8 jeans. She had just turned 32 when we met, which made her a bit younger than me. We had a lot of interests in common, though, and there was an instant chemistry we both felt. It didn't take long before we found an excuse to get a drink together, and soon after that we became lovers. Although we weren't dating "exclusively," I really liked her and we had a great time in bed.
One night after as-usual amazing sex, she started asking me about things I had tried... what I had loved, what I hadn't, what I wanted to try, what I was afraid to try. I answered her questions pretty honestly- I'm not shy, but there are also a lot of things I haven't tried, so I think I probably fall somewhere in the middle. As I I told her about each experience (sex in public, sex with strangers, threesomes) she asked probing questions: How did it happen? How did it feel? Would I do it again?
It was kind of fun, the type of things lovers often do- and anyway, I liked hearing her stories. She seemed endlessly curious about sex, and told me some things she wanted to try.
Finally I began teasing her about her questioning. "So why are you so interested?"
"I'm just interested. I like you!" she responded. "And I want to try new things with you. I want to see you experience things you haven't experienced before."
"I'm sure."
"Well... would you be open to that?"
"Sure. I think so."
"OK. How far would you be willing to go?" she asked.
Hmm. How to answer a question like that? "I think I would be willing to try about anything, as long as it's just between us and it doesn't involve blood or bruising."
"Hmm..." she responded. "There's a lot I could do with that..."
I leaned over to kiss her. "I'm sure. But be gentle with me!"
"I promise nothing. You'll get what you deserve."
"Oh really. You think you could make me moan?" I asked, joking.
"Oh, I think I could make you scream," she replied confidently, batting her eyelashes dramatically.
I laughed, putting on my best you can't scare me smile. "I doubt it. But what did you have in mind?"
She smiled and slowly reached over and opened her bedside drawer. When she returned, she held a flesh-colored dildo about six inches long and an inch and a half thick. Raising her eyebrows, she trailed it down over my stomach and tapped it on my thigh.
I looked down and realized what she was implying. I laughed. "Oh, really..."
She laughed too, but there was mischief in her eyes. "So... what? You're scared? Don't trust me?"
I felt a little defensive. I didn't want her to think I didn't trust her; I did. The thought was intriguing... maybe it would feel good? "Well no, its just... just..."
"What?" she asked, all innocence.
So big. "Well it just that... that's too big. I can't take something like that."
She giggled. "Of course you can."
"What?"
"Well, a girl has to take that much... right? And we do. And we're smaller."
"Well, yeah but..." Damn. She had a point. I had taken her in the ass a half dozen times, and watched as her pretty pink asshole expanded to take my non-insignificant cock.
"And when we give birth..."
"OK, that's different..."
"What about when you fisted me?"
It was true; I had put my whole hand inside her, about a month ago. The memory made me stiffen. It had taken about an hour to work up to, lots of lube, lots of relaxation, but in the end she had taken it inside her. The sight of my hand disappearing into her swollen vulva was one I still fantasized about.
"That was hot," I admitted. "So... what? You want your turn?"
"I want to work up to it. I think it would be really sexy. Would you let me?"
It was a yes or no question, and there didn't seem to be any downside right now to saying "yes." Besides, it was really hard to tell this girl anything but "yes" when she was perched next to you half naked with emerald green eyes.
"Yes. I guess?"
She grinned. "Good boy." She hopped off the bed and grabbed her laptop, propping it open on her lingerie patterned lap.
"What are you up to?" I asked, suspicious.
"Nothing, silly boy. Don't you worry, I know what you need..."
I rolled my eyeballs. Well, this should be something, I thought.
Nothing happened for a couple weeks; in fact, we both got busy and didn't see each other much. Toward the end of the third week I got a text from Meg that asked if I was up for a film festival that weekend. Hell yes, I told her, eager both to get out of the house and to see her again.
The date proceeded as expected; we went out to dinner, we saw a couple of artsy movies, drank some wine at a local bar. After a few glasses we started making up stories about random people we saw across the room, what kind of sex they were into and what they would do if propositioned cold by one or the other of us. It was fun; Meg was devious and cute, and I think her wicked smile could have convinced a lot of people to take a chance. Fortunately it was just me going home with her that night.
After our fourth drink she leaned over to me and whispered, "I have something for you... at home..."
I played along. "Reeeally. And what would that be?"
"A package," she whispered conspiratorially.
"Hmm. And what's inside this package?"
"Something for you. Just for you. Come home with me and see..."
I guess I couldn't refuse that offer. I was reasonably drunk and ready to see her naked. When we got back to her apartment, I could see the hints of that devious smile on her face- almost like there was a secret she was just dying to tell, but couldn't. At this point I was pretty much entranced by her charms and ready to do whatever she asked.
Which, as it turned out, was a good thing.
She got us some more wine and we went to her bedroom. I took off my pants and my shirt and my socks and lay down on her frilly white bed. She lit some candles and went into her closet, changing out of her dress into panties and a brown satin blouse that only accentuated her taut stomach and full, voluptuous breasts. She looked amazing, actually. Like a dream of sexiness.
She came to the side of the bed and I started to get up, but she put her hand on my chest and lightly pushed me back down. I was lying on my back, head propped up on a pillow, my underwear still on. The light from the candles cast a soft orange glow around the room as she kissed me softly.
"Scoot over." I did as I was told, scooting to the other side. She climbed up on the bed on her knees, and reached for my underwear. She grabbed the sides and I lifted my ass up, allowing her to slide the boxer-briefs off in one smooth motion.
"Mmmmm..." she said, running her hands over my chest and thighs. Her hands danced around my prick, but she was careful to avoid it- which of course only made me harder. Then, she dramatically lowered her lips to my cock and took it in her mouth in one wet gulp, pressing her nose against my pubic mound to prove she had taken it all. I groaned, her soft hair caressing my stomach as she pumped slowly, up and down.
"Mmmm," she said again, coming up for air. "You're such a big boy." Kneeling next to me, she took my wet cock in her hand and moved her mouth up to kiss me again. I was entranced; this was all very sensual. She lightly stroked my cock as she moved her lips down my neck, across my chest, and onto my right nipple. It stiffened and I let out a quiet gasp as she ran her tongue across it, then lightly closed her teeth around it. Casually, she slipped her left hand up and grabbed hold of my hair, tugging my head back into the pillow as she moved to my left. Between her left hand holding my head, her mouth roaming my chest and her other hand kneading my cock, I was in sensual heaven.
She must have sensed that I had grown compliant, for she lifted her head, let go of my hair and jumped off the bed to retrieve a cardboard box under the bed. Out of it she lifted a small, black velvet bag with some lumps in it, then a bottle of what I could only guess was lube. She put the box back on the ground and then held up the black bag dramatically, prying open the top with her other hand. Out of the top emerged a flash of color, then the rest of the velvet fell away to reveal a full 8-inch purple dildo with a thick 2 1/2 inch swirly bump protruding at a right angle from the top. A small cord traced out the back to a remote, so I decided it must be a vibrator as well.
"WHAT is that?" I asked, suspiciously.
"That is for you, my love, and you're going to learn to like it. I'm going to teach you."
"Oh Meg, I don't know..."
"But I do. So relax. Lean back, and enjoy it. I promise you, we won't do anything you don't like. I'm going to break you in sloooowly."
Something about the way she said that last part got my adrenaline going, and probably helped overwhelm whatever hesitation I was feeling. "OK," I laughed nervously. "You're the boss."
"That's right," she said, without missing a beat. "Now, put your legs up."
I did as I was told, bending my knees so that my feet were flat on the bed. She reached down and grabbed a pillow and a towel lying at the foot of the bed. "Lift up." I did, and she slid the pillow under my ass and covered it with the towel. I sat back down, my ass now elevated a couple inches off the bed.
"Now. Are you relaxed?"
I laughed. "No. I have no idea what you're going to do to me."
She looked at me in the eyes. I couldn't see the green of her eyes in the candlelight, but I knew they were there. "Well, do you trust me?"
"Yes."
"OK. Then relax. You're going to like this..."
"Yeah?"
"Yeah."
She stayed kneeling beside me on the bed and leaned over to take my cock back in her mouth. While making wet, slurping sounds, she reached for my balls with her right hand and began tugging them lightly. It felt really good, but also soothing. Soon her hand strayed southward and she placed a single fingertip on my ass and began rubbing in circles. I could feel myself clenching, but since she wasn't pushing there wasn't any resistance- just light friction on the surface. Once I started to focus on the sensations, it felt pretty good.
"Do you like that?" she asked innocently.
"Um, yes, actually. That feels good."
"Good," she smiled. "Now I'm going to give you a little lube."
My heart was racing. She was lubing me; wasn't that dirty? Would she think I was less manly? But I didn't think less of her for taking my cock in her ass, and anyway she didn't seem anything but excited. I relaxed and tried to focus on the anticipation, turning it into something pleasurable. After a second I felt her finger return, now slippery, and it probed gently at my entrance. The sensations were new, but with the lube there was barely any friction.
She returned for more lube, spreading a large drop on her fingertip and then circling and massaging it gently inside. As she worked more and more into my ass, my resistance melted and soon she had her moistened finger in past the first knuckle. She began making slow, sensuous circles inside, pulling gently against the muscle. I felt myself resisting, then releasing, relaxing with her massage. She tugged a little farther and I let her stretch my tight spincter. It was weird, but it felt sexual and vulnerable too. What was happening to me?
"Still feel good?" she inquired.
I nodded. As if my rock hard cock didn't tell her.
"Good. Now, I'm going to pop your cherry."
"You are?" Stupid question.
"I am. Focus on relaxing. Relax your body. Focus on the feeling." I tried, but part of me was still resisting.
She withdrew her wet finger and applied another drop of lube. By now I was enjoying the sensation of being "wet"- almost like her pussy, I thought. Is this how girls feel? Wow, I thought, if I was going to say anything... if I was going to stop... this would be the time. But I didn't.
Meg dobbed the lube at my entrance and pushed her moistened finger back in to the first knuckle. She met the back spincter but, instead of stopping, she pushed slowly but insistently. After only a second, she pushed past the resistance and was in to the other side. I expected that she would pause, but instead she kept going and pushed her wet finger all the way in.
Woah. Before the sensations were coming from the sensitive nerves around the outside. This was different. There was a violation and a pressure from inside, but a good kind. My ass was trying to close but it couldn't. It was strange, vulnerable, but I liked it.
"There. I told you you would like it." I hadn't said anything, but she must have seen it on my face. "Now, I'm going to loosen you up. Keep relaxing." She took her finger and began moving it back in and out of my ass, just an inch out and an inch back in. As she drew out I could feel a little bit of a vacuum, and when she drove back there was a satisfying feeling of having the vacuum filled again. She started taking longer strokes and at the end, she would twist a little, screwing into me. I was still tight, but I was definitely lubed and there was no doubt she was fucking my wet ass with her finger. There was no resisting it.
Maybe it was that realization that did it, but psychologically something shifted. I started to focus on the feeling and really relax. I gave myself over to being fucked by her. My mind relaxed and my spincter released too, which to my surprise only increased the pleasure. Whereas before I was clenching tight against her, now she was able to withdraw entirely and easily dip back inside inside my wet and open orifice. When she withdrew and added a second finger, I clenched for a second but she pushed right past it, taking surprisingly little resistance. It went in with a bit of a wet sound, and now she began pumping faster with her whole arm.
I couldn't help it. I groaned...
"Good! I think you're ready now." She withdrew her fingers with a wet pop, wiped them on the towel, and reached for the big purple toy. Shit. I had almost forgotten all about it, I had been so intent on feeling her fingers inside me. I watched as she positioned the bulb end at the edge of her pussy, and then slowly pushed it in so that the base of the toy went right up against her pubic bone. She then locked it in place with a small leather belt that looped up between her ass like a g-string. Her nipples were erect and she looked really sexy with the seven inch purple phallus extending straight up from her groin. But I felt anxious, and I could feel myself tightening back up.
"Oh God..." I let out, breathlessly. "Is this going to hurt?"
"Hmmm. Maybe a little..." she whispered. "But now you'll know how we feel, the first time a girl takes it in the ass." Oh God. What could I say? Like I said, I had taken her in the ass a half dozen times- and though I always tried to be gentle, I had also driven forward with lust. I craved her ass, the feel of it, to be inside her... did that mean she wanted to be inside me?
Still kneeling, she rolled a condom down over the toy and positioned herself in front of me. My legs were still spread, but now she lifted them off the bed and scooted closer so that she was sitting with her folded legs under mine. She reached back and pressed the remote control, once, twice, and the toy began a low but persistent hum as she nudged it up against my lubricated hole. My brain lit up as the vibrations against my nerves fired a cascade of sensations.
"Can you feel that?" she asked.
"Yes!" I let out. "Can you?"
"Yes," she nodded. "The bullet is in the head, but it kind of spreads throughout the toy. So theres's some stimulation from the part inside me, and the part up against my clit. And of course from watching your face."
"Ohhh..." I said, somewhat nonsensically. I was focusing on the feeling spreading around my pelvis. I could feel the tip pressing against the sensitive flesh and something was taking hold of me. She hadn't penetrated me, but now I wanted her to. I trusted her, and I wanted her inside me. I wanted her to fuck me.
Holding my cock with her right hand, and positioning her toy with her left, she pushed gently and my ass stretched to accommodate. The head of her toy was pressed hard up against my backside, half an inch in, and the vibrations spread all throughout my ass. It felt amazing. My back spincter resisted, though- it was just too big.
"Tell me what you're feeling," Meg whispered.
"It feels... good," I responded, somewhat vaguely. But she wasn't satisfied.
"Baby, I want to see the look on your face as I press this cock inside you. I want you to tell me, too. Tell me how you feel. In detail."
"It feels... warm. Exciting. Sexy. Vulnerable."
"Keep going."
"I like it. My heart is racing. I'm afraid, but I also want you..."
"'You want me' what?"
"I want you to keep going."
"To keep going, what?"
It all came tumbling out. "To fuck me. I want you to fuck me. Please, fuck me. I trust you, it feels so good, I want you to fuck me, even if it hurts."
Her eyes lit up, and she looked so happy. "Good," she whispered. "Because that's what I'm going to do. I'm going to fuck you with this strap-on, and you're going to like it. I'm going to make you moan, and I'm going to make you scream, and you can cry also if you want to."
And with that, she doubled the pressure and I could feel the vibrating purple head pressing up hard against the second ring of my ass. I felt myself opening, involuntarily, physically and psychologically. I realized I wasn't going to be able to resist her, and in only a couple seconds, she popped the head into the other side. I felt a quick stab of pain, and then a rush of pleasure as I got used to the new situation.
"Goood..." she said, encouragingly. "Good boy. I knew you could take it. Just relax now. Breathe. Enjoy the feeling."
I did as she told me. As I breathed in and out, I could feel myself relaxing and the pleasure increasing. The vibrations almost seemed to be massaging my insides, and without really trying to I could feel my resistance lessening.
"Does that feel good?" she asked.
I nodded. "Yes."
"Now I'm going to show you something else. Something you'll like..."
This was all new, and I already liked it, but what did she have in mind? I could feel the vibrating bullet inside the head of her cock, causing a rush of new sensations inside me as the vibrations spread through my ass. It was intense, but also arousing and completely vulnerable.
WIth her previous lubrication, she pushed and effortlessly gave me another inch, and then another. There was no friction to the smooth intrusion, but I could feel my insides filling up and a pressure and a strange warmness. Was this right? Was this wrong? I didn't have time to decide, it was all just happening.
Then she settled into place and I noticed a different sensation, emanating from deep inside me but spreading into the inside of my cock. It felt half like I was going to come, and half like I was going to urinate- it felt good, but I was also worried I might actually pee. She had the head of her cock pressed up at an angle against the roof of my ass, and the vibrations were spreading through my nerves there and doing something...
The feeling intensified. "No I... Meg I... What..." I moaned uselessly, turning my head from side to side and clawing at the sheets. I didn't know what I was doing. Still perched between my legs and slightly below me, with her ankles on either side of her ass, she started rocking upward softly, back and forth, pressing the vibrating head again and again in the same spot, while holding my cock upright in her hand...
And then something happened- I came. Or it seemed like I did, because although there were no contractions, a thin white liquid came streaming out of my upright cock and over her hand. It didn't shoot into the air, it just bubbled up like a well. She stopped her rocking and moved my cock to her left hand. Then she brought her right hand up to her face, licking the fluid dripping off her hand. Then she wiped the rest on her chest.
"Oh my God!" I laughed, half delirious. "What was that?"
"That was your prostate, I would guess. And it seems to be working!" I had heard of prostate massage before, but this was certainly different. Her cock was still vibrating inside me, but she had stopped rocking and I took several long, deep breaths. Weirdly, I felt more relaxed that ever. It felt like the most natural thing to have her inside me. It was full, but it felt comfortable and sensuous.
"So," she said, with a wicked smile. "Do you want more?"
"There's more?"
"Yes. You said you wanted me to fuck you, and I want to fuck you too. Really fuck you. I've been gentle so far, like I promised. I want you to feel comfortable. But if you let me, I'm going to really fuck you now. I may not be so gentle. And no matter what comes out of your mouth, I'm going to keep going until I'm done. Until I've come."
Wow. We were in different territory now, and I hesitated. As if she was reading my mind, she gently pulled the toy out of my ass a half-inch...
"No..." I moaned.
"'No'?"
"I mean yes. Yes. Yes. OK."
She smiled a wicked grin. "OK. Wrap your legs around my back." With my ass already raised by the pillow, bringing up my legs tilted my pelvis farther back toward the ceiling. She rose from a sitting position and leaned over me, with her weight on her hands and knees- almost like we were in a reverse missionary position. Her marvelous C-cup breasts dangled down from her body, and she poised with her cock positioned just inside me. She looked beautiful and sexy and powerful.
"Ready?" she asked.
I didn't know, but instead I just nodded.
With that, she began slowly sinking the wet purple cock into my upturned ass. The vibrating head pushed against the back of my bowels, and my vision blurred as she sunk three, then four, then five inches inside of me. My asshole clenched uselessly, and I actually saw stars. I gasped loudly. She kept going. It was so intense that part of me wanted to stop, but I also didn't, and anyway she was in control now...
She stopped an inch from the end and pulled slowly back, one, two, then thee inches. Then back in, a little faster now. With my legs in the air and the substantial lube, I gave surprisingly little resistance. Now out, now back in. It was still slow and sensual, but there was adrenaline rushing through my system from the panic of being violated so completely. I was thrashing from side to side.
Then she leaned down and wrapped her arms around my neck, kissing me fully on the lips. As she did, she used her hips to push the dildo alllll the way in, hitting the back of my ass. But she kept going, pushing into new territory. I let out a moan that changed in pitch until it was approaching a scream.
"Shhhh... " she whispered. "You're going to tell all my neighbors that I'm fucking you! Here," she said, grabbing another pillow and placing it over my head. "Now you can make as much noise as you want."
"Mmmmmh," I answered. But it made less noise, so I felt OK to let out a little more. "MMMMMHHH...!" She pulled out and then quickly thrust back in again, for the first times she started fucking me with a rhythm. I felt totally helpless: she was fucking me, hard and deep, and I was loving it. I had my legs around her and I was edging her on even as I was screaming into the pillow. I didn't care what I sounded like. The pain and the pleasure felt so good, and I was so turned on by having this beautiful woman on top of me.
In the distance I could hear her moaning too, a low moan that undulated with the thrusts she was delivering. "Uhhh, uhh, uhh, uhh...". I knew from past experience that she was in her own world now, totally focused on her own pleasure, and building toward an explosive orgasm. She made the same sounds when I was fucking her and she was getting close. I could feel her breasts pressed up against my chest and her hips grinding into me, and my forgotten cock was sandwiched in her soft belly.
Suddenly she moved up off of my chest, and I thought maybe she had come, so I took the pillow off my head. But she was only switching positions, sitting back on her ankles upright as I lay prone. She wrapped both her arms around my legs and began pulling me toward her as she thrust into me, faster and faster. The dual force of her pulling and thrusting doubled the impact as her vibrating cock hammered into me, and somewhere in the back of my mind I was worried about whether she was pushing lube out of me onto the bed. But Meg was no longer focused on me. She was staring off into space as she fucked me, with a look that was somewhere between rapture and anxiety. And her moan only got higher. Finally she fucked me with four hard finishing blows as she came, shuddering in a way that I could feel throughout my body. She collapsed on top of me, her six inch dildo lodged far into my ass, still vibrating.
For about a minute Meg didn't move at all, and I focused on catching my breath. Then she groped for the remote and clumsily turned it off. Carefully, she slipped out of the harness and then withdrew the sloppy wet cock from inside me. All I could think of was falling asleep, and for once, she was in the same mood. She wrapped the toys in a towel, pushed it to the side of the bed and cuddled up beside me. Within minutes we were both asleep, and I was dreaming of what might happen tomorrow.
I met Megan ("Meg") while I was teaching at a local university. She was the T.A. for another class in my department, and had similar interests, so we hit it off right away. She was about 5'6" and had long, dark hair and pretty green eyes. She was pretty athletic, but had enough weight to fill out a nice "C-cup" and size 8 jeans. She had just turned 32 when we met, which made her a bit younger than me. We had a lot of interests in common, though, and there was an instant chemistry we both felt. It didn't take long before we found an excuse to get a drink together, and soon after that we became lovers. Although we weren't dating "exclusively," I really liked her and we had a great time in bed.
One night after as-usual amazing sex, she started asking me about things I had tried... what I had loved, what I hadn't, what I wanted to try, what I was afraid to try. I answered her questions pretty honestly- I'm not shy, but there are also a lot of things I haven't tried, so I think I probably fall somewhere in the middle. As I I told her about each experience (sex in public, sex with strangers, threesomes) she asked probing questions: How did it happen? How did it feel? Would I do it again?
It was kind of fun, the type of things lovers often do- and anyway, I liked hearing her stories. She seemed endlessly curious about sex, and told me some things she wanted to try.
Finally I began teasing her about her questioning. "So why are you so interested?"
"I'm just interested. I like you!" she responded. "And I want to try new things with you. I want to see you experience things you haven't experienced before."
"I'm sure."
"Well... would you be open to that?"
"Sure. I think so."
"OK. How far would you be willing to go?" she asked.
Hmm. How to answer a question like that? "I think I would be willing to try about anything, as long as it's just between us and it doesn't involve blood or bruising."
"Hmm..." she responded. "There's a lot I could do with that..."
I leaned over to kiss her. "I'm sure. But be gentle with me!"
"I promise nothing. You'll get what you deserve."
"Oh really. You think you could make me moan?" I asked, joking.
"Oh, I think I could make you scream," she replied confidently, batting her eyelashes dramatically.
I laughed, putting on my best you can't scare me smile. "I doubt it. But what did you have in mind?"
She smiled and slowly reached over and opened her bedside drawer. When she returned, she held a flesh-colored dildo about six inches long and an inch and a half thick. Raising her eyebrows, she trailed it down over my stomach and tapped it on my thigh.
I looked down and realized what she was implying. I laughed. "Oh, really..."
She laughed too, but there was mischief in her eyes. "So... what? You're scared? Don't trust me?"
I felt a little defensive. I didn't want her to think I didn't trust her; I did. The thought was intriguing... maybe it would feel good? "Well no, its just... just..."
"What?" she asked, all innocence.
So big. "Well it just that... that's too big. I can't take something like that."
She giggled. "Of course you can."
"What?"
"Well, a girl has to take that much... right? And we do. And we're smaller."
"Well, yeah but..." Damn. She had a point. I had taken her in the ass a half dozen times, and watched as her pretty pink asshole expanded to take my non-insignificant cock.
"And when we give birth..."
"OK, that's different..."
"What about when you fisted me?"
It was true; I had put my whole hand inside her, about a month ago. The memory made me stiffen. It had taken about an hour to work up to, lots of lube, lots of relaxation, but in the end she had taken it inside her. The sight of my hand disappearing into her swollen vulva was one I still fantasized about.
"That was hot," I admitted. "So... what? You want your turn?"
"I want to work up to it. I think it would be really sexy. Would you let me?"
It was a yes or no question, and there didn't seem to be any downside right now to saying "yes." Besides, it was really hard to tell this girl anything but "yes" when she was perched next to you half naked with emerald green eyes.
"Yes. I guess?"
She grinned. "Good boy." She hopped off the bed and grabbed her laptop, propping it open on her lingerie patterned lap.
"What are you up to?" I asked, suspicious.
"Nothing, silly boy. Don't you worry, I know what you need..."
I rolled my eyeballs. Well, this should be something, I thought.
Nothing happened for a couple weeks; in fact, we both got busy and didn't see each other much. Toward the end of the third week I got a text from Meg that asked if I was up for a film festival that weekend. Hell yes, I told her, eager both to get out of the house and to see her again.
The date proceeded as expected; we went out to dinner, we saw a couple of artsy movies, drank some wine at a local bar. After a few glasses we started making up stories about random people we saw across the room, what kind of sex they were into and what they would do if propositioned cold by one or the other of us. It was fun; Meg was devious and cute, and I think her wicked smile could have convinced a lot of people to take a chance. Fortunately it was just me going home with her that night.
After our fourth drink she leaned over to me and whispered, "I have something for you... at home..."
I played along. "Reeeally. And what would that be?"
"A package," she whispered conspiratorially.
"Hmm. And what's inside this package?"
"Something for you. Just for you. Come home with me and see..."
I guess I couldn't refuse that offer. I was reasonably drunk and ready to see her naked. When we got back to her apartment, I could see the hints of that devious smile on her face- almost like there was a secret she was just dying to tell, but couldn't. At this point I was pretty much entranced by her charms and ready to do whatever she asked.
Which, as it turned out, was a good thing.
She got us some more wine and we went to her bedroom. I took off my pants and my shirt and my socks and lay down on her frilly white bed. She lit some candles and went into her closet, changing out of her dress into panties and a brown satin blouse that only accentuated her taut stomach and full, voluptuous breasts. She looked amazing, actually. Like a dream of sexiness.
She came to the side of the bed and I started to get up, but she put her hand on my chest and lightly pushed me back down. I was lying on my back, head propped up on a pillow, my underwear still on. The light from the candles cast a soft orange glow around the room as she kissed me softly.
"Scoot over." I did as I was told, scooting to the other side. She climbed up on the bed on her knees, and reached for my underwear. She grabbed the sides and I lifted my ass up, allowing her to slide the boxer-briefs off in one smooth motion.
"Mmmmm..." she said, running her hands over my chest and thighs. Her hands danced around my prick, but she was careful to avoid it- which of course only made me harder. Then, she dramatically lowered her lips to my cock and took it in her mouth in one wet gulp, pressing her nose against my pubic mound to prove she had taken it all. I groaned, her soft hair caressing my stomach as she pumped slowly, up and down.
"Mmmm," she said again, coming up for air. "You're such a big boy." Kneeling next to me, she took my wet cock in her hand and moved her mouth up to kiss me again. I was entranced; this was all very sensual. She lightly stroked my cock as she moved her lips down my neck, across my chest, and onto my right nipple. It stiffened and I let out a quiet gasp as she ran her tongue across it, then lightly closed her teeth around it. Casually, she slipped her left hand up and grabbed hold of my hair, tugging my head back into the pillow as she moved to my left. Between her left hand holding my head, her mouth roaming my chest and her other hand kneading my cock, I was in sensual heaven.
She must have sensed that I had grown compliant, for she lifted her head, let go of my hair and jumped off the bed to retrieve a cardboard box under the bed. Out of it she lifted a small, black velvet bag with some lumps in it, then a bottle of what I could only guess was lube. She put the box back on the ground and then held up the black bag dramatically, prying open the top with her other hand. Out of the top emerged a flash of color, then the rest of the velvet fell away to reveal a full 8-inch purple dildo with a thick 2 1/2 inch swirly bump protruding at a right angle from the top. A small cord traced out the back to a remote, so I decided it must be a vibrator as well.
"WHAT is that?" I asked, suspiciously.
"That is for you, my love, and you're going to learn to like it. I'm going to teach you."
"Oh Meg, I don't know..."
"But I do. So relax. Lean back, and enjoy it. I promise you, we won't do anything you don't like. I'm going to break you in sloooowly."
Something about the way she said that last part got my adrenaline going, and probably helped overwhelm whatever hesitation I was feeling. "OK," I laughed nervously. "You're the boss."
"That's right," she said, without missing a beat. "Now, put your legs up."
I did as I was told, bending my knees so that my feet were flat on the bed. She reached down and grabbed a pillow and a towel lying at the foot of the bed. "Lift up." I did, and she slid the pillow under my ass and covered it with the towel. I sat back down, my ass now elevated a couple inches off the bed.
"Now. Are you relaxed?"
I laughed. "No. I have no idea what you're going to do to me."
She looked at me in the eyes. I couldn't see the green of her eyes in the candlelight, but I knew they were there. "Well, do you trust me?"
"Yes."
"OK. Then relax. You're going to like this..."
"Yeah?"
"Yeah."
She stayed kneeling beside me on the bed and leaned over to take my cock back in her mouth. While making wet, slurping sounds, she reached for my balls with her right hand and began tugging them lightly. It felt really good, but also soothing. Soon her hand strayed southward and she placed a single fingertip on my ass and began rubbing in circles. I could feel myself clenching, but since she wasn't pushing there wasn't any resistance- just light friction on the surface. Once I started to focus on the sensations, it felt pretty good.
"Do you like that?" she asked innocently.
"Um, yes, actually. That feels good."
"Good," she smiled. "Now I'm going to give you a little lube."
My heart was racing. She was lubing me; wasn't that dirty? Would she think I was less manly? But I didn't think less of her for taking my cock in her ass, and anyway she didn't seem anything but excited. I relaxed and tried to focus on the anticipation, turning it into something pleasurable. After a second I felt her finger return, now slippery, and it probed gently at my entrance. The sensations were new, but with the lube there was barely any friction.
She returned for more lube, spreading a large drop on her fingertip and then circling and massaging it gently inside. As she worked more and more into my ass, my resistance melted and soon she had her moistened finger in past the first knuckle. She began making slow, sensuous circles inside, pulling gently against the muscle. I felt myself resisting, then releasing, relaxing with her massage. She tugged a little farther and I let her stretch my tight spincter. It was weird, but it felt sexual and vulnerable too. What was happening to me?
"Still feel good?" she inquired.
I nodded. As if my rock hard cock didn't tell her.
"Good. Now, I'm going to pop your cherry."
"You are?" Stupid question.
"I am. Focus on relaxing. Relax your body. Focus on the feeling." I tried, but part of me was still resisting.
She withdrew her wet finger and applied another drop of lube. By now I was enjoying the sensation of being "wet"- almost like her pussy, I thought. Is this how girls feel? Wow, I thought, if I was going to say anything... if I was going to stop... this would be the time. But I didn't.
Meg dobbed the lube at my entrance and pushed her moistened finger back in to the first knuckle. She met the back spincter but, instead of stopping, she pushed slowly but insistently. After only a second, she pushed past the resistance and was in to the other side. I expected that she would pause, but instead she kept going and pushed her wet finger all the way in.
Woah. Before the sensations were coming from the sensitive nerves around the outside. This was different. There was a violation and a pressure from inside, but a good kind. My ass was trying to close but it couldn't. It was strange, vulnerable, but I liked it.
"There. I told you you would like it." I hadn't said anything, but she must have seen it on my face. "Now, I'm going to loosen you up. Keep relaxing." She took her finger and began moving it back in and out of my ass, just an inch out and an inch back in. As she drew out I could feel a little bit of a vacuum, and when she drove back there was a satisfying feeling of having the vacuum filled again. She started taking longer strokes and at the end, she would twist a little, screwing into me. I was still tight, but I was definitely lubed and there was no doubt she was fucking my wet ass with her finger. There was no resisting it.
Maybe it was that realization that did it, but psychologically something shifted. I started to focus on the feeling and really relax. I gave myself over to being fucked by her. My mind relaxed and my spincter released too, which to my surprise only increased the pleasure. Whereas before I was clenching tight against her, now she was able to withdraw entirely and easily dip back inside inside my wet and open orifice. When she withdrew and added a second finger, I clenched for a second but she pushed right past it, taking surprisingly little resistance. It went in with a bit of a wet sound, and now she began pumping faster with her whole arm.
I couldn't help it. I groaned...
"Good! I think you're ready now." She withdrew her fingers with a wet pop, wiped them on the towel, and reached for the big purple toy. Shit. I had almost forgotten all about it, I had been so intent on feeling her fingers inside me. I watched as she positioned the bulb end at the edge of her pussy, and then slowly pushed it in so that the base of the toy went right up against her pubic bone. She then locked it in place with a small leather belt that looped up between her ass like a g-string. Her nipples were erect and she looked really sexy with the seven inch purple phallus extending straight up from her groin. But I felt anxious, and I could feel myself tightening back up.
"Oh God..." I let out, breathlessly. "Is this going to hurt?"
"Hmmm. Maybe a little..." she whispered. "But now you'll know how we feel, the first time a girl takes it in the ass." Oh God. What could I say? Like I said, I had taken her in the ass a half dozen times- and though I always tried to be gentle, I had also driven forward with lust. I craved her ass, the feel of it, to be inside her... did that mean she wanted to be inside me?
Still kneeling, she rolled a condom down over the toy and positioned herself in front of me. My legs were still spread, but now she lifted them off the bed and scooted closer so that she was sitting with her folded legs under mine. She reached back and pressed the remote control, once, twice, and the toy began a low but persistent hum as she nudged it up against my lubricated hole. My brain lit up as the vibrations against my nerves fired a cascade of sensations.
"Can you feel that?" she asked.
"Yes!" I let out. "Can you?"
"Yes," she nodded. "The bullet is in the head, but it kind of spreads throughout the toy. So theres's some stimulation from the part inside me, and the part up against my clit. And of course from watching your face."
"Ohhh..." I said, somewhat nonsensically. I was focusing on the feeling spreading around my pelvis. I could feel the tip pressing against the sensitive flesh and something was taking hold of me. She hadn't penetrated me, but now I wanted her to. I trusted her, and I wanted her inside me. I wanted her to fuck me.
Holding my cock with her right hand, and positioning her toy with her left, she pushed gently and my ass stretched to accommodate. The head of her toy was pressed hard up against my backside, half an inch in, and the vibrations spread all throughout my ass. It felt amazing. My back spincter resisted, though- it was just too big.
"Tell me what you're feeling," Meg whispered.
"It feels... good," I responded, somewhat vaguely. But she wasn't satisfied.
"Baby, I want to see the look on your face as I press this cock inside you. I want you to tell me, too. Tell me how you feel. In detail."
"It feels... warm. Exciting. Sexy. Vulnerable."
"Keep going."
"I like it. My heart is racing. I'm afraid, but I also want you..."
"'You want me' what?"
"I want you to keep going."
"To keep going, what?"
It all came tumbling out. "To fuck me. I want you to fuck me. Please, fuck me. I trust you, it feels so good, I want you to fuck me, even if it hurts."
Her eyes lit up, and she looked so happy. "Good," she whispered. "Because that's what I'm going to do. I'm going to fuck you with this strap-on, and you're going to like it. I'm going to make you moan, and I'm going to make you scream, and you can cry also if you want to."
And with that, she doubled the pressure and I could feel the vibrating purple head pressing up hard against the second ring of my ass. I felt myself opening, involuntarily, physically and psychologically. I realized I wasn't going to be able to resist her, and in only a couple seconds, she popped the head into the other side. I felt a quick stab of pain, and then a rush of pleasure as I got used to the new situation.
"Goood..." she said, encouragingly. "Good boy. I knew you could take it. Just relax now. Breathe. Enjoy the feeling."
I did as she told me. As I breathed in and out, I could feel myself relaxing and the pleasure increasing. The vibrations almost seemed to be massaging my insides, and without really trying to I could feel my resistance lessening.
"Does that feel good?" she asked.
I nodded. "Yes."
"Now I'm going to show you something else. Something you'll like..."
This was all new, and I already liked it, but what did she have in mind? I could feel the vibrating bullet inside the head of her cock, causing a rush of new sensations inside me as the vibrations spread through my ass. It was intense, but also arousing and completely vulnerable.
WIth her previous lubrication, she pushed and effortlessly gave me another inch, and then another. There was no friction to the smooth intrusion, but I could feel my insides filling up and a pressure and a strange warmness. Was this right? Was this wrong? I didn't have time to decide, it was all just happening.
Then she settled into place and I noticed a different sensation, emanating from deep inside me but spreading into the inside of my cock. It felt half like I was going to come, and half like I was going to urinate- it felt good, but I was also worried I might actually pee. She had the head of her cock pressed up at an angle against the roof of my ass, and the vibrations were spreading through my nerves there and doing something...
The feeling intensified. "No I... Meg I... What..." I moaned uselessly, turning my head from side to side and clawing at the sheets. I didn't know what I was doing. Still perched between my legs and slightly below me, with her ankles on either side of her ass, she started rocking upward softly, back and forth, pressing the vibrating head again and again in the same spot, while holding my cock upright in her hand...
And then something happened- I came. Or it seemed like I did, because although there were no contractions, a thin white liquid came streaming out of my upright cock and over her hand. It didn't shoot into the air, it just bubbled up like a well. She stopped her rocking and moved my cock to her left hand. Then she brought her right hand up to her face, licking the fluid dripping off her hand. Then she wiped the rest on her chest.
"Oh my God!" I laughed, half delirious. "What was that?"
"That was your prostate, I would guess. And it seems to be working!" I had heard of prostate massage before, but this was certainly different. Her cock was still vibrating inside me, but she had stopped rocking and I took several long, deep breaths. Weirdly, I felt more relaxed that ever. It felt like the most natural thing to have her inside me. It was full, but it felt comfortable and sensuous.
"So," she said, with a wicked smile. "Do you want more?"
"There's more?"
"Yes. You said you wanted me to fuck you, and I want to fuck you too. Really fuck you. I've been gentle so far, like I promised. I want you to feel comfortable. But if you let me, I'm going to really fuck you now. I may not be so gentle. And no matter what comes out of your mouth, I'm going to keep going until I'm done. Until I've come."
Wow. We were in different territory now, and I hesitated. As if she was reading my mind, she gently pulled the toy out of my ass a half-inch...
"No..." I moaned.
"'No'?"
"I mean yes. Yes. Yes. OK."
She smiled a wicked grin. "OK. Wrap your legs around my back." With my ass already raised by the pillow, bringing up my legs tilted my pelvis farther back toward the ceiling. She rose from a sitting position and leaned over me, with her weight on her hands and knees- almost like we were in a reverse missionary position. Her marvelous C-cup breasts dangled down from her body, and she poised with her cock positioned just inside me. She looked beautiful and sexy and powerful.
"Ready?" she asked.
I didn't know, but instead I just nodded.
With that, she began slowly sinking the wet purple cock into my upturned ass. The vibrating head pushed against the back of my bowels, and my vision blurred as she sunk three, then four, then five inches inside of me. My asshole clenched uselessly, and I actually saw stars. I gasped loudly. She kept going. It was so intense that part of me wanted to stop, but I also didn't, and anyway she was in control now...
She stopped an inch from the end and pulled slowly back, one, two, then thee inches. Then back in, a little faster now. With my legs in the air and the substantial lube, I gave surprisingly little resistance. Now out, now back in. It was still slow and sensual, but there was adrenaline rushing through my system from the panic of being violated so completely. I was thrashing from side to side.
Then she leaned down and wrapped her arms around my neck, kissing me fully on the lips. As she did, she used her hips to push the dildo alllll the way in, hitting the back of my ass. But she kept going, pushing into new territory. I let out a moan that changed in pitch until it was approaching a scream.
"Shhhh... " she whispered. "You're going to tell all my neighbors that I'm fucking you! Here," she said, grabbing another pillow and placing it over my head. "Now you can make as much noise as you want."
"Mmmmmh," I answered. But it made less noise, so I felt OK to let out a little more. "MMMMMHHH...!" She pulled out and then quickly thrust back in again, for the first times she started fucking me with a rhythm. I felt totally helpless: she was fucking me, hard and deep, and I was loving it. I had my legs around her and I was edging her on even as I was screaming into the pillow. I didn't care what I sounded like. The pain and the pleasure felt so good, and I was so turned on by having this beautiful woman on top of me.
In the distance I could hear her moaning too, a low moan that undulated with the thrusts she was delivering. "Uhhh, uhh, uhh, uhh...". I knew from past experience that she was in her own world now, totally focused on her own pleasure, and building toward an explosive orgasm. She made the same sounds when I was fucking her and she was getting close. I could feel her breasts pressed up against my chest and her hips grinding into me, and my forgotten cock was sandwiched in her soft belly.
Suddenly she moved up off of my chest, and I thought maybe she had come, so I took the pillow off my head. But she was only switching positions, sitting back on her ankles upright as I lay prone. She wrapped both her arms around my legs and began pulling me toward her as she thrust into me, faster and faster. The dual force of her pulling and thrusting doubled the impact as her vibrating cock hammered into me, and somewhere in the back of my mind I was worried about whether she was pushing lube out of me onto the bed. But Meg was no longer focused on me. She was staring off into space as she fucked me, with a look that was somewhere between rapture and anxiety. And her moan only got higher. Finally she fucked me with four hard finishing blows as she came, shuddering in a way that I could feel throughout my body. She collapsed on top of me, her six inch dildo lodged far into my ass, still vibrating.
For about a minute Meg didn't move at all, and I focused on catching my breath. Then she groped for the remote and clumsily turned it off. Carefully, she slipped out of the harness and then withdrew the sloppy wet cock from inside me. All I could think of was falling asleep, and for once, she was in the same mood. She wrapped the toys in a towel, pushed it to the side of the bed and cuddled up beside me. Within minutes we were both asleep, and I was dreaming of what might happen tomorrow.
Rowan
- 19.12.2022
- 21
- 0
