Many years have passed since I was Rob's sissy boy. As I write about those times, I relive the memories of how much I enjoyed each new experience. My love of lingerie is still strong with me. But sex is now only with my wife.
We renewed our affair after I had returned late at night from Tim's. The door closed slowly as my brother stepped towards my bed, naked. I reluctantly reached and switched on the lamp. Turning my head back, I was staring up at his bobbing six-inch boy bone. It danced just above my nose. I rose up to take it between my puffy lips. As I did, my covers slid down to my waist.
Seeing the top of my teddy exposed, Rob broke the silence saying, "I see you're still dressed for fun. Did you get your ass pounded tonight?"
I nodded "yes" as I swallowed his head.
He than said he wanted sloppy seconds. I nodded my acceptance and began to chew on his hard meat. I would have loved to have him fuck me any other time, but after Tim me earlier, I could've have passed that night. When Rob was home a month earlier, he told me he was done with guy sex. So I was surprised that he was in my room looking for some ass. I hoped if I let him have me now then when he came back on his next school break he might be willing to fuck again.
I was tired but as I sucked on his shaft, I began to regain some of my energy. A warm hard cock will do that. I reached around to grab his bare ass. Pulling him on to my bed. He kneeled beside my face then swung a leg across my shoulders. Now he was straddling my neck. His cock slipped in and out between my tender lips, his sack banged against my chin. My head was propped by pillows, allowing me to lay back while Rob face fucked me.
His slow, even strokes drove his head to the back of my throat. Between his soft moans, Rob told me that it had been two months since he had any pussy. He admitted that seeing me in panties earlier got him hard. He than decided he would fuck me when I got in. Rob said that he had been waiting hours, and was ready to explode.
I turned my face to the side, his cock slipped out. Thinking Rob might be horny enough make a threesome, I said, "I'm glad you changed your mind. Maybe we can find other ways to help satisfy you while your home."
At the time I don't think he picked up the full meaning of my statement. He just grinned and fed me his slick cock again. Rob proceeded to slow fuck my mouth, while I thought of a way to suggest he join Tim and I. He leaned forward, rocking his hips, screwing my mouth, as he held onto the headboard.
The covers over my legs were too warm, so I reached down and threw them off exposing my garter and nylons. Rob turned to the sight of me completely exposed. He also could see my sissy cock poking against the crotch of the teddy. Rob reached back and stroked my bulge. My revived boy clit jumped at his touch. He reached down between my thighs to the crotch and pulled, releasing the snaps to the teddy. My tiny cockette sprang up to its full four and one-half inches. It felt good to be free. Rob grabbed and began to jerk me off. I was in heaven. My mouth was full of cock, and my dickey was being slowly pumped.
With my eyes closed and my lips softly massaging Rob's pole, I placed a hand on each of his bum cheeks again. With a firm hold of Rob's tight ass, I kneed and squeezed him as I drew him closer. Rob's cock was forced deeper into my mouth.
Rob meanwhile stopped pulling on my cock, slipping his hand down to my sack. My dickey twitched as his fingers rolled my balls around. He jiggled and patted my nut sack, like a boy with a bag of marbles. To give him easier access, I raised my knees to the sides of his waist lifting my bum up off the bed. With my pussy presented to him, he slid his hand from my balls to my rosebud. Shivers ran over my bum. I wanted his fingers to enter me, but instead they danced around my puckered hole, teasing me to madness. Then as if he knew I couldn't take any more, his middle finger dove into my gooey ass. I let out a low moan that vibrated his cock, still tucked between my warm lips. I knew he would feel the sticky mix still coating my innards. His digit slipped in without any resistance. I was loose and ready.
Rob teased me by saying, "Feels like your fluids are a little low. I guess I can fill you back up."
I released his cock and replied, "I could use a good flushing too." Rob grinned, while looking back at me.
At this point I had to lower my legs, the position was hard to hold. When I rolled my ass back onto the bed, my pussy made a sucking sound as Rob's finger was drawn out. His sticky finger slid across my thigh and hooked onto a garter strap. He tugged on it then let it snap back against my bare skin. I kept trying to suck his cock back in. But with him twisting about, I couldn't get it into my mouth. It bobbed and bounced, tapping against my nose and chin. I had saliva and pre-cum smeared all over my face. I couldn't close my mouth quick enough to catch it.
Finally I released a cheek and grabbed his shaft. It was to far away to get my lips around it, but I could kiss and flick it with my tongue. While my tongue wiggled at his cock hole, Rob turned to watch. I tongue fucked his cock for a minute, until Rob pulled it away saying that I was driving him crazy. I closed my eyes and put my head back onto the pillows to rest.
As I relaxed, Rob began to shift himself about. He rose up onto his knees. Still straddling me, then move down along my body. At my hips, his bare ass slid up against my cockette. It poked itself up between his cheeks. The head had to be near his asshole. Rob stopped and paused, seeming to enjoy my sissy cock's pressure at his brown eye. Watching him, I saw Rob with hands on his thighs, ever so slightly raised and lowered his bum. His eyes shut as he moved only his ass. I was now sure my head was at the entrance of his fuck hole. Rob soon began to make small circles against my head. Lightly rubbing his ass lips over the tip as he moaned. I would have loved for him to sit down on me right then.
Rob had other things in mind. He stopped, opened his eyes. Looked back at me, then slid over my cockette and down onto my legs. My sissy cock sprang up as he passed over, aching for more attention. He positioned himself onto my calves.
There he sat on my stocking wrapped legs. Lightly, he began to run his hands up my legs, to my hips and back down again. He must've liked my outfit, because his eyes stared down as if hypnotized. I closed my eyes and drifted with the sensation of his touch.
Rob shifted his weight forward, then I felt his warm breath surround my cock head. Through slits in my eyelids, I saw Rob's mouth slowly engulfed my boy clit. Once past the head, Rob closed his lips around my shaft and slid down its short length. I watched him until his nose buried itself into my pubes. I groaned and stroked his hair. Rob slipped his hands under my bum and squeezed my cheeks as he sucked me. Rarely did Rob do more than lick and kiss my sissy cock. But tonight he opened himself up. I hoped this wasn't a onetime thing. Maybe he was now accepting our affairs as just sex, right or wrong. Rob was far more sexual than before, I decided to lay back and enjoy the reversed rolls.
After fucking Tim earlier, it would take a bit more of Rob's oral attention to get me to shoot. But I was willing to let him continue for as long as he had a mind to. If he wanted to drink my jizzum than I would try to oblige him. I laid still, letting small moans escape my throat as Rob sucked and licked. He seemed to be enjoying himself. For having little practice, he was quite good.
To my complete surprise, my balls began to tighten up. I felt them swell full of warm cream. I was quickly approaching the point of no return. I told Rob I was ready to cum, but he continued to orally service me. I closed my eyes as the joy of my pending release took me. Rob's pace picked up just as the first blasts were shooting into his mouth. The first couple shots caught him by surprise. He stopped bobbing and held still. The following blasts filled his mouth. I could feel his try to swallow. He gulped once then, I felt sticky goo slid down into my pubes. He wasn't ready for the taste. But he kept his mouth lightly wrapped around my head, sucking and lapping.
After the last drops of spunk had oozed from my head, Rob ran his sticky tongue and lips along my length. He seemed to like the slick sensation as they glided against one another. He was relaxed and enjoying the moment.
I was just a puddle under him. My body was completely drained as if I had fed him the last of my strength. I wanted to sleep. But of course Rob wanted more. He now wanted his boy juice to be coxed out from his sack, and not by my lips.
Rob rose with man-milk dripping on his chin, wiped it off and got off the bed. He asked if I had any oil. I told him in the back of the closet in a box. As he turned and leaned into the dark closet, I sat up on my elbows to direct his search. He bent down and pulled out a couple boxes. I told him which one had the lube.
Placing both boxes near the bed, he lifted off the lid. Exposing panties, garters, bras and nylons inside. I told him it was probably at the bottom. Rob stuck his hand in and blindly searched by feel until he found the bottle. As he pulled the oil out, I told him to take out the blue panties, garter and some stockings. He asked why.
"For you to wear." I replied
Rob weakly protested that he didn't want to or need to wear panties to fuck me.
I said, "You don't need to wear them, but I think you'll like the feel once they're on."
He again protested but with little conviction. He slowly picked out the items and tossed them onto the bed.
He said, "You'll have to help."
I answered, "Just like you did for me, the first time I put on mom's things."
He said nothing as I told him to set on the edge of the bed. I sat up and hopped off on to my feet. My crotch was a sexy mess as I wiped myself before reaching for one of the nylons. Kneeling at his feet, I carefully slipped a stocking onto each leg up to his knees. Before having Rob stand to attach the garter straps, I placed a hand on each knee and spread them apart. Leaning in, I gobbled his cock into my hungry mouth.
I bobbed down and up, teasing Rob for a few minutes. Then I stopped, leaned back on my heels and had Rob stand. I had him turn with his ass in my face. Once he obeyed, I again leaned forward, this time I stuck my tongue between his cheeks. Bob surprised me again by bending at the waist, giving me better access to his bum. I flicked and licked up and down his crack until he couldn't stand it any more and moved away, driven crazy by my teasing.
I said, "Ok, I'll stop. Now stand still while I hook the belt."
Rob moved back as I took the garter belt and reached it around his waist. After it was hooked, I pulled both stockings up and attached them in the back. Next, I had Rob spin around. Before he was completely turned, I caught his semi-hard cock between my lips. I sucked him deep as I blindly attached each stocking in front. I stayed like that for a while, my lips locked on Rob's shaft, returning the favor.
Finally I released his tasty cock and held the panties open as Rob stepped into them. I slowly slid them up over his silky legs, attempting to tease him in the process. By the way Rob's cock jerked wildly, I knew he was hooked on wearing lingerie. As the waistband slid up under his cock, Rob groaned softly. I gently lifted his shaft up and back, tucking it against his tummy. Rob then help to slip the panties up to his hips. Jokingly I asked Rob if he wanted a bra.
He replied, "Not tonight, maybe next time."
I looked up at him and smiled, saying, "I knew you would love these. I think most guys who enjoy stroking a girl in her lingerie secretly wishes they could feel what its like to wear them. They're just too embarrassed to try."
I then offered to Rob, "Wear anything I have if he like while you're home. Just be careful not to leave them for mom to find."
He said sheepishly, "Thanks, if I feel the urge, I'll let you know before I take anything."
I then said, "You'll find that the more you wear them, the more you'll want to wear them more. Especially to bed." Then laughed.
I rose to my feet and sat on the bed. Rob turned and stepped in between my legs. Our nylon wrapped legs rubbing together, both our cock were now hard and twitching. As I wrapped my arms around his waist, I drew him closer. Rob slipped a hand under each of my thighs and raised them up. This forced me to let go and fall onto my back.
My legs were now bent at the knees and in the air. Rob moved closer until his thighs were hard against my bum. His cock, covered in nylon, bounced and twitched against my naked sissy cock. The sexy contact in the panties had Rob ready to shoot his load.
He then surprised me by saying, "I'm going to fuck you like a bitch."
I wasn't sure if I could take another hard fuck, but I shot back, "You're the second guy to tell me that tonight."
Rob asked, "Does he dress up too?" as he pushed my legs up and back, causing my bum to roll up off the bed once more.
I smiled up at him saying, "Yea, sometimes in his wife's panties."
Well that did it. Rob seemed shocked as he asked, "You're fucking a married guy? How old is he?"
"Not much older, five or six years. And he's someone you would've never guessed." I replied with a smug smile.
Rob was getting hornier from our conversation. He leaned his hips forward into my ass cheeks, prodding his nylon coated cock head at the base of my cockette . Through his panties, the wetness from his pre-cum smeared over my balls. Sensing he wanted to know more about my new cockman. I tried to give out more details but my mind was fading back to his cock rubbing against mine. I kept losing my concentration.
I told Rob, "He's like me, started wearing panties as a teenage. Then he wore his wife's. Now he has some of his own, and he likes to be fucked."
Rob, in an inquisitive voice, asked, "Do I know him?"
"Yea, you've seen him and you're always saying how his wife is 'so fucking hot' when you see her at the store." I replied, knowing I gave away to much information.
Rob's mouth dropped open. With disbelief in his voice, he asked, "You mean Tim, your manager?"
I smiled proudly and with a nod said, "That's him."
He whispered loudly, "Holy shit, his wife is fucking perfect. Why does he fuck a guy with a babe like her?"
I raised my head saying, "Its about length, and its not that he's short."
Rob wanting to know more, asked, "What's that mean?"
I then giggled as I told him, "He's too long for her. He's got a ten inch cock that doesn't fit in her six inch hole."
Rob, still having trouble believing me, asked, " So he fucks you instead of his wife?"
Grinning, I said, "No, he still screws Sue, but she can't satisfy him totally. She's not willing to try it anally. He was willing to live with it until he caught me in my panties in the restroom one night."
As Rob's head nudged and slid at my cockette and sack, in disbelief, he repeated, "Holy shit, and you've fucked his ass?"
"Yea, tonight." I said, "He asked for it."
I held back from saying anymore, not sure whether to approach Rob with my proposal. But, I figured what better time to talk about fucking another guy than just before he fucked me.
So I asked him, "Would you like to join us? Tim asked if I knew anyone who might be interested in making it a threesome. I didn't say anything about us until I was sure you would agree. Maybe we can all meet this week at the store after closing, if you interested."
Rob's prodding developed into pumping as I brought up the idea to him. I knew he was even hornier after he heard about Tim. He seem to also be daydreaming. As if he was picturing the three of us sucking and fucking each other.
I laid with my eyes shut, as he quietly rubbed into me. Our steady cock to cock action and erotic talk had us both ready. I didn't say anymore about us and Tim, letting Rob mull it over for awhile.
Rob released a leg and reached down to his crotch. I could tell he was freeing his cock from it panty prison. It flopped out tapping at my thigh. He grabbed the oil and began to lube his head and my pussy. He was completely silent, like he was thinking about what I had been telling him. Trying to decide if he would join us. He was going through the motions but wasn't all there.
Once we were oiled up, he aligned his head against my tender ass. He leaned into me, his cock head easily slipped in with no pain or resistance. After Tim had stretched me earlier, my ass opened like a flower. My feet were up at his shoulders, his hands locked on my bare thighs. Rob slowly drove himself inside. I moaned from pure pleasure. The talk had gotten me hotter too. I wanted him to pound me like a jackhammer.
When he was tucked deep inside, he stood quiet, as if lost in his thoughts. After a while, I asked him if he was "ok".
He said, "Yea, are you?"
I told him, "Never better."
Well that brought him around. He pulled out then back in. He started a nice steady rhythm. I raised my head up to watch Rob in his sexy things as he plowed my ass. Rob had worn panties once at the drive-in, but he was more into it this time. He stared down at me, concentrating on his meat-pop being lovingly squeezed by my hungry pussy.
Ron picked up his pace and began to slam into me, saying, "You're so fucking nice. Then he stunned me by asking, "When can we get together?"
My mind was in a fog. I hadn't expected Rob to discuss any possible meeting until after we had finished. I had been focused solely on his boy bone filling my ass. I snapped out of it and thought for a few seconds.
As my head jerked about from Rob banging into me, I replied, "If you're sure about it, I think we can meet in a couple days." My voice was jerky, sounding like I was riding a bike on a bumpy road.
I was thrilled to hear Rob was willing to get together with Tim. As I started to think of the combinations that we could come up with, Rob was pounding me harder. I tried to rock back to meet his thrusts, but Rob was controlling both of us.
Rob was working me harder than ever before. Both sets of my cheeks, ass and face, were quivering for his force. With thoughts of Rob and Tim fucking me, I was ready to explode. I knew from Rob's frantic fucking, he was too.
In my dreamy state, I felt a hand wrapped around my cock. Rob began to pump me as he drilled my pussy. I laid in complete joy of the moment. Although I had shot a load earlier, I was near blowing again. Rob's piston like cock, drove into me, throwing me around like a rag doll.
Through all of this Rob blurted out, "Yea, I'll join you."
Well that did it. Suddenly my balls shot short spurts of cream out onto my stomach and Rob's hand. As I squirted like a mini fountain, Rob's cock swelled. He began releasing a flood of cum into my waiting ass. I drew my legs closer to my chest, giving him a straight shot. He splashed my innards as he pumped out and in. Rob began growling as he punish-fucked me. It was like he wanted to prove he was as good a Tim was. As if he was in competition with him. If that was the case, than I would be the one to benefit by it. If these guys try to out fuck each other, I would need my rest.
Rob was finally weakening. He slowed his pace as his jets of hot seed began to turn to light sprays, then to dribbles. He continued to drive his shaft deep but with a more leisurely glide through my gooey hole. At this point I was totally exhausted. I could have fallen asleep right then and sleep for a week.
Rob leaned forward once more then extended his arms on to the bed for support. He was trying to catch his breath and calm down. He hovered over me while grinding his hips into my bum. Poking his shrinking cock around. His eyes closed as he took in the last sensations of our sex.
When he had enough, Rob leaned back, straightened up. Stepping back, his limp cock slipped out with a slurping sound. That was followed by the sound of compressed air escaping from my bum hole. Then the gooey mix from the evenings activities seeped out.
Rob garbed my used shirt and wiped himself. Next he cleaned my well stretched ass as best as he could. I scooped the cum off my teddy and tummy. Then licked it up.
I lifted my head and asked Rob, "Don't those things feel great?"
He smiled and said, "If its that good every time, I might wear them more often."
I said, "I think our discussion about a threesome with Tim helped too."
Rob thought for a moment then said, "I'm not so sure now about doing that. I might freak out."
"No you won't." I said reassuringly, "Tim's real nice and easy going. Plus he won't tell anyone. He doesn't want to mess up his marriage. And his long cock is so good"
I sat up and Rob stepped back away. He started to pull down his panties. I asked him what he was doing. He told that me he was taking them off and go to bed.
I said, "Leave them on and the garter and stockings too. You'll probably find you have a harder time falling asleep but a much sexier sleep."
Rob replied, "Alright, I'll try them tonight, then drop them off tomorrow morning."
I told him that that was fine. Rob adjusted his outfit, and turned to leave. I reached out and patted his sissy ass as he headed out the room.
Before the door closed, I said, "You look very sexy in them." Then giggled.
Sore and exhausted from the long night of screwing, I could barely turn off the lamp and crawl under the covers. I knew my bum was leaking but I didn't care. I just wanted to sleep. It took only a second to drift off.
After what seemed like just seconds of deep sleep, I felt my body being rolled onto my stomach. I couldn't figure how I was moving since I didn't roll on my own. My eyes were still closed, not wanting to wakeup. Without my help, the covers were pulled off and my hips lifted up until my knees were under me. There I was, half-asleep with my bare ass in the air. My mind wasn't working quite right yet. I still hadn't figured out what was going on. In the darkness I sensed that someone else was in the room, on my bed.
Suddenly I felt my pussy being forced open by something pushing inward. It wasn't painful but more annoying. I seemed to be getting fucked without being asked. I opened my eyes slightly. Still dark in the room, with what little strength I had left, reached back behind me to touch who ever was slipping his cock into me. As I expected, I felt the silky leg and garter clasp of Rob.
Weakly protesting, I asked, "Aaah, what the hell are you doing? It's the middle of the night. Couldn't you wait 'til tomorrow?"
Meanwhile, he had sunk his cock head in as far as it would go. I was so loose he could have put his fist in.
Knowing he wouldn't leave until he was finished, I didn't try to get away. It was kind'a neat having late night sneaky sex. I probably could have slept through the whole think. I was just there for him to cum into.
Bob whispered, "I couldn't help it. I woke up hard and horny. I needed to fuck."
In a pissed tone I whispered, "Couldn't you have just jerked-off?"
He said, "I tried but it wasn't good enough, and since you're next door."
I was resigned to the fact that Rob was going to fuck my ass. I would have to wait until he was done to get back to sleep. He gripped my hips and began to work into my well fucked pussy. I faded in and out with sounds of Rob's hips slapping against my cheeks and his grunts haunting the quiet of the night. He used no finesse. He slammed in with his full weight then pulled out quickly. I think he pulled too far a couple times and his dick slipped out. I know when he slipped out once, he wipe his cock off of his and Tim's previous gifts, using my sheet. My face was jammed into the pillows. I had to struggle to breath at times. I could've smothered and he won't have known.
Rob was enjoying his late night sex as he sawed in and out. He was rejuvenated since his earlier visit. He kept whispering, "I'm so fucking horny, I could fuck you again."
I was hoping it was only lust talk. I couldn't take another fucking. I just wanted to sleep. I asked, "What time is it?"
In between his groans, he said, "Five."
I mumbled, "It's only been a couple hours. Next time, don't wait two months."
I prayed that he would shoot soon. Thankfully he did. Rob finally climaxed, splashing my innards with another load of creamy cum. I only wished that he would finish quickly and leave. He bucked into me a few times then collapsed down on top of me. We both slid down onto the bed. I didn't care if he stayed or left, I was going back to sleep.
Just before I passed out, I felt Rob's cock being withdrawn. He rolled off of me, and bed, then out the door. As the door closed, I drew the covers up over my drained body for some well deserved rest.
I'll write about our threesome at the store soon.