Robs Sissy Boy

Now married and in my fifties, my love of lingerie controls most of my waking and sleeping hours, as it did when I was a teenager. For about a year while in high school, my brother Rob fucked me while I was dressed in lingerie. But on his first visit home from college, he told me that he no longer wanted guy sex. At the time I was stunned and disappointed. I hadn't had more than a titty feel and some french kissing with a girl. I was lonely and horny.

After a few weeks, Tim and I found each other. Our storeroom lust gave us both an outlet for our sexual needs. Tim couldn't get his cute wife to take his ten-inch cock all the way and I needed ten inches of cock up my sissy ass. I had fucked Rob's ass once. I hoped to fuck Tim's ass during our next meeting.

We both wore panties at work, sometimes with a garter and stockings when we were scheduled to work together. One evening during the week between Christmas and New Years, Tim came back to the stockroom after locking up. I was sitting on some boxes dressed in only pink satin panties, a garter and nylons. He had already unbuckled his belt and was unfastening the button on his slacks as he made his way through the stockroom doors. He stepped in between my parted legs as I stroked myself. Slowly unzipping his pants, they fell to the floor. I reached into his floral colored panties for his stiffing cock. Leaning forward, I took it in my mouth. We both moaned in satisfaction. While I slipped his cock in and out between my lips, my hand stroked his balls still trapped in his panties. I slid my other hand up along the back of his thigh. Reaching his bum and slipped my fingers up under his leg band. Slowly inching my fingers over to his butt crack.

When my finger poked between his cheeks, it caught Tim's attention. He gasped. I tried to maintain my rhythm on his pole while creeping closer to my target, his rosebud.

When my middle finger found its mark, Tim did not protest. I felt now was my opportunity to see how far Tim would allow me to go. I pressed lightly at his hole as I moaned onto his cock. Tim held still. With more pressure, my fingertip started inward.

I got to the first knuckle then stopped. Tim groaned, leaned forward placing his hands on my shoulders. This allowed me easier access. My finger sank in to the second knuckle. Now halfway in, I wiggled it a little to see his reaction. Tim remained still, letting out another moan. He was really enjoying the dual attention.

Tim told me earlier that he could only stay long enough to let me swallow his milky load, but wanted to talk about getting together later in the week. As I poked and wiggled, Tim tensed up then let lose a gush of hot cum. A flood of jizzum filled my mouth and poured down my throat. He bucked into my face as my finger stayed buried. He feed me more cream then I could handle. Some squeezed through my lips and down my chin. Dripping on to my panties and cock below.

After sucking Tim's last drops from his smooth balls, he cleared his throat and asked, "Are you free Friday night?"

With his cock still in my mouth, I mumbled, "Yes."

Tim said, "Sue will be out visiting family."

While sucking his now shrinking rod, I mumbled, "Saturday is New Years Eve."

He answered, "Yea, she'll be back on Saturday. We'll have the Friday night to ourselves."

As Tim's cock shank, I let it pop from my mouth. He began to straighten his clothes still with my finger deep inside. It felt like a pair of lips sucking hard on it. Tim didn't try to remove it. I watched his cock returned to its five-inch soft length, wiped my chin and licked my finger clean. Finally I slowly withdrew my finger from his bum. With both hands free, I opened his panties and tucked him back in.

As Tim stepped back and pulled up his pants, he said, "You can follow me home after work Friday night. Bring a change of panties to freshen up in."

We quickly finished dressing then left the store. I drove home fantasizing how great Friday would be. I would drive to Tim's house in my new used car I had bought a couple weeks earlier.

Friday afternoon, I was anxiously nervous as I planned what I would wear to work and what I would take with me to Tim's. Alone at home, my parents and younger brother were away until Saturday. I sat naked on my bed with my boxes of lingerie opened before me on the floor. After changing my mind time and again, I decided to wear my black satin bikinis to work, than change into my white teddy and a garter belt with stockings.

I was hard and tempted to pull my sissy cock for relief, but I had only an hour to get to work. Placing the items on the bed that I was to wear, I closed the boxes and put them far back into my closet. Then pranced back to my bed to pull on my panties.

After sliding the bikinis on, I sat on the bed, and slip on my socks than reached for my jeans. Suddenly my bedroom door swung open. I froze in terror expecting it to be my mom or dad. Instead, Rob walked in. Rob was home between semesters. He stepped in. I relaxed a bit, but wasn't sure if he would be disgusted seeing me in panties.

I smiled and said, "Hi. You do like to scare me, don't you?"

He had a mischievous grinned, as he replied, "Yea I do. I see you still wear girl's underwear. Where're you going?"

I replied, "I guess I just can't stop. I'm going to work, then out."

Rob asked with a surprised voice, "Out with a girl?"

As I slipped a leg into my pants, I said in a soft tone, kind of ashamed, "No. Not with a girl."

He snapped back, "Do I know him."

I said, "You might."

"Well, its up to you who you want to go out with." He said. I sensed hurt in his voice. He said, "I just came home to change, than I'm going back out."

I began to pull on my jeans as Rob turned to the door.

I said, "See yea later."

Rob replied, "Yea, see yea." slamming the door behind him. I wasn't sure if he was in a hurry or pissed.

But I didn't think much of it and finished dressing then drove to work. During the evening in the store, Tim and I didn't see much of each other. After closing, I worked in the stockroom straightening and sweeping up as the others cleaned out in the store. As I finished up, Tim spoke over the announcing system say, " Get your ass up front so we can get out of here." I threw off my apron and quickly walked to the front of the store. Tim locked up and we headed to our cars. I was so excited as I followed Tim to his place.

Once inside his house, Tim said I could take a shower first if I wished. He was always considerate. I accepted his suggestion as I followed him into his bedroom. With my bag in hand, I watched his long lean body as he walked through the house in front of me. I couldn't wait until we were both dressed in our lingerie.

I placed my bag by the bed. Tim asked if I wanted a beer. I told him, a coke was fine. He showed me the bathroom then left to get our drinks. I look around his bedroom and saw a dresser that I assumed belonged to his wife. I opened the top drawer. Inside were Sue's bras and panties, most of them of cotton. After a minute of rummaging through her things, I closed the drawer and bent down to open the lower one. There I found socks and PJ's. But also, there were a few things of satin and lace. I pulled out a pair of pink lace panties and held them to my waist as Tim walked in. I was concerned that he may be pissed that I was going through Sue's things.

Instead, he said as he handed me my drink, "That's about the sexiest stuff she has, those and the red satin panties that you like. You probably saw her cotton things. That's all she'll wear. Nothing sexy, its tough trying to get excited in bed when she's dressed like that."

I replied, "She's a very cute girl. To bad she doesn't dress sexier for you."

Tim said, "That's just the way she is. I'd love that she would dress up for bed. If she felt sexy, maybe she would be more willing to do the things I want her to do. Instead, she won't try anything different, always with me on top. That's why I need this tonight."

I smiled and put the panties back. After taking a drink, I headed into the bathroom, intentionally leaving the door ajar. I undressed leaving my worn panties in plain view for Tim to see. Then I stepped into the shower and began to lather up. Through the curtain, I saw Tim's silhouette near the in the room. He seemed to pick up my panties and put them to his face. I was soaping up when the curtain opened. I was hoping Tim would shower with me. My cock was already hard as I turned to watch him stepped in. His cock was also at full length, but twice the size as mine. I soaped up my hands than holding the bar of soap, I began to scrub Tim as he stood facing me.

I couldn't keep my hands off his pole, soaping his cock and balls. After lathering his cock up, I moved my hands up his waist, his firm tummy then up to his chest. There I paid most of my attention to his nipples as they harden. Softly rubbing his chest for a few minutes, then back down to his cock again. I couldn't keep my hands off of it.

I reluctantly released his boy bone and slipped my hands up to his hips, than wrapped my arms around his waist. Leaning into him, we rubbed our slick bodies against each other. Tim stood silent as I moaned in soapy lust. It was so sexy, his smooth hard body slick with soap. We were both wet and slippery. I could have dropped to my knees right then. My sissy cock was poking below Tim's balls. His long cock was forced down between my legs. I didn't want to break my embrace.

But Tim said, softly, "Turn around, I want to soap you up."

That was one of only a few things that could get me to release him. I loosened my embrace, stepped back and turned around. With little patience, I waited for Tim's large hands to begin caressing my body. I heard as he lathered up his hands then put down the bar of soap. Tim couldn't start washing me fast enough.

Finally Tim placed his soapy hands at my waist, than slipped them to my stomach. He gently rubbed my belly while teasingly slipping a hand down to my pubes. My cockette twitched each time he drew close. After a few minutes, his hands slid up to my chest. Cupping each of my boy breasts, he lightly rubbed over each. With Tim's attention to my nipples, they began to tighten up. Now like girly tits, he pinched and squeezed them, sending little shots of pleasure/pain through my body. I was also aware of Tim's hard cock, lightly tapping at my sack, between my slightly parted legs. My knees were weakening.

Tim leaned back away from me as he continued to caress my breasts. This allowed his cock to spring up and slip in against my bum crack. Tim then leaned back into me, trapping his ten-inch cock between my cheeks, like a hot dog tucked in a bun. I was in heaven. As he roamed his hands down and up my body, his rod slid along my crack. I tilted my bum back and up, trying to get his head to hit my pussy hole. But I was just too short. Tim was deliberately trying to drive me nuts.

His hands slowly moved down until he wrapped one around my sissy cock. Then with the other hand, gently cupped my balls. My head was tilted back and my breathing was heavy. Tim's mouth was above my ear, as he whispered how he couldn't wait to fill my ass. My legs were turning to rubber.

I groaned as he worked me all over. His hands at my cock, his cock between my cheeks and his hot breath in my ear and on my neck. I was ready to let go and shoot my hot load into Tim's hand. But Tim suddenly stopped, released me and leaned away. I was so disappointed.

When I turned my head toward him, Tim said, "Why don't you soap up my bum."

I smiled. I was stunned. I had hoped to coax Tim into letting me fuck him, but I didn't expect him to ask for it. Maybe I was ahead of myself. Maybe he just liked me touching his asshole, not screwing it. But with this chance presented to me, I was going to see how far I could go.

I turned around to see Tim bending over, extending his arms, places his hands on the wall. His bum was thrush back toward me, waiting. I gabbed the soap and quickly worked up a thick soapy foam. Lightly, I placed my hands on his tight bum, and began to make creamy circles on each cheek. I teased him by slipping a hand up and down through his crack. He would press back so slightly when I did this, seaming to enjoy the attention I gave to his puckered hole. I could hardly control the urge to poke a finger inside. My fingers danced around and at his entrance, watching his head and listening to his breathing. Looking to find clues of his willingness to go farther. I removed my hands and leaned into Tim's bum. My tiny cock slipped between his cheeks, my head at the edge of his asshole. I squirmed myself over his cheeks, my pubes were squashed against his soapy bum. I could have fucked him right there. After a minute of rubbing together, I decided to see if Tim would be accepting of my probing finger. Without warning, my middle finger at his opening, slid in half way. I waited for Tim to react.

Tim gasped, held still, then said, "Go ahead, deeper."

I slowly pushed until my finger was completely in. I stopped, waiting to allow Tim to adjust to my invasion. I then pulled back a little then back in again. Tim lowered his head and moaned. Pulling out, I added a second finger and began to force my way back in. My soapy fingers slipped deep in with little resistance. I began to pull out when Tim thrush his ass backwards sucking my finger back in. I knew now he wanted me inside. I started to saw my fingers out and in, harder and faster. He moaned and groaned with each stroke. I noticed that as I pumped in, tiny bubbles floated out from his bum. I smiled at this, thinking how sexy it seemed.

I had been finger-fucking Tim for a minute or so when Tim said in a panting voice, "I've asked Sue to finger me a couple times but she wanted nothing to do with it." Then he said, "Lets get out and dress."

With that, I pulled out my finger, and stepped back to rinse off. As I leaned into the water, I felt that the water had turned cooler. Quickly rinsing, I stepped out. Tim followed close behind.

I picked up a towel and wrapped it over my back, then took a second towel and waited as Tim stepped out. With a satisfied smile on his face, he got out and turned off the water. I draped the towel over him, rubbing his back dry. He said that we could go into the bedroom and finish drying ourselves. I went first. Tim followed, teasingly pinching my ass as we hurried into the room.

Once in the room, we quickly dried ourselves. I watched Tim from behind as he bent over, drying his himself. His long legs spread slightly exposing his smooth sack and semi-hand cock swaying as he moved. Knowing I might soon be shooting a load in his ass, seemed to make him look sexier.

I dropped the towel then picked up my bag. Pulling my lingerie out, I laid them on the bed. Tim turned to see what I had brought. As I separated my things, Tim reached under the bed pulling out a large black briefcase. He placed it on the bed and opened it. Inside were various styles and colors of panties, bras and garters. He reached in with both hands and scooped out all the lovely items.

Dropping them on the bed, he asked, "What should I wear?"

I smiled, than stepped closer to him. I leaned over the pile and searched through the lace and satin, trying to separate each piece. I made smaller piles of just panties, bras, garters and stockings. Then Tim and I began to form sets by color and material.

I asked, " When did you buy all this?"

Tim answered, "I figured that if I went shopping for lingerie before Christmas, salesladies would figure I was buying for my wife. I went to Sears and Penney's and some women stores. After the first store, I was more comfortable and started to buy anything I liked. I keep the briefcase in the car trunk. Sue thinks it's for work."

I said, "You've got a very nice selection. I see a couple things that I would like to have myself."

Tim grinned and said, "Go ahead take something."

I said, "No, I couldn't. I've got too much already."

Tim replied, "Go on. I insist. If you want, we'll trade. I saw a few things of yours that I would like."

I said, "Really! I guess we could do that. This way we won't get bored with our things. We can switch back and forth."

I already had my eye on a pretty white garter belt. It was satin with lace trim and little pink roses on each strap and one on the front of the belt.

Picking it up, I looked at Tim and said, "Do you mind if I choose this. I'll trade with the garter I was going to wear tonight. It was white satin and lace with satin bows in place of the roses"

He smiled and sad, "That's great. I think the bows look just as sweet.

I held the belt to my waist and quickly hooked it. I couldn't wait to get dressed. Tim sat on the bed as I reached for my nylons. He said he would watch me then dress after. I smiled and sat on a chair to roll on the stockings. After they were up to my thighs, I stood up and began to attach them to the claps. As I bent to hook up the front of the first hose, Tim got up off the bed and stepped over next to me.

He said, "I'll hook them up in the back."

I could feel him bend then stretch the nylon and straps from behind. When I finished my right leg I switched to the left. Tim was still hooking the first. After I attached the left leg I remained bent, leaving my bum sticking back in Tim's face. Before he move to the left leg he placed a few kisses on my cheeks then ran his tongue up along my crack. This sent goose bumps all over my bum.

He noticed them and said, "That must've hit the spot."

I replied, "Yea, but not as good as the spot you'll hit with this." As I reached back grabbing his cock.

Tim grinned then moved over and hooked the back of the left stocking. I straightened up and told him, "Thanks, now go sit down. I'll finish up then help you."

He went and sat on the bed, as I took the teddy, gathering it in my hands. Rose my arms, letting my hands slip up into the shoulder straps. The teddy fell down over my head and shoulders. I got stuck for a minute with my arms tight inside as I tried to shimmy the teddy down. While in my awkward position, Tim with his long arms reached over and began to pinch my bum. Then pulled on the garter straps, letting them snap against my thighs when he released them. I wiggled and moved away finally getting my head and arms free. Once my arms were through, I quickly pulled the teddy down to my waist. With the garter belt under, I pulled the front and back flaps down. Reaching between my legs, stretching the flaps until the crotch snaps were together. The teddy had underwire cups built into the top. My own boy boobs filled them up to about a size "A" cup. I wasn't fat but I did have soft boobs.

Tim said, "They look perfect in the cups. Good enough to suck."

I turned to face the mirror, with my back to Tim. I liked what I saw.

I heard him mumble, "Bring that ass over here and I'll eat it."

Without saying a word I turned sideways, bent slightly at the waist, stuck out my bum then stood on my tippy-toes. Imitating those forties pin-up girls poses I always loved. Sexy long legged girls dressed in flimsy sheer lingerie or shorts, wearing shoes or slippers with six-inch heels, sticking their ass out.

Tim just said, "Very sexy."

After holding my pose for a few more seconds, I straightened up and moved back to the bed next to Tim. I leaned on to the bed and selected a blue sheer nylon bra, panties and garter for Tim to wear. Picked up a nude stocking, rolled it up in my fingers then knelt down and slipped it up Tim's legs. I did the second stocking then told Tim to stand up. Once on his feet, hooked the garter around his waist then stretched one stocking to the clamps and attached it. While shifting to his other leg, I stopped to nibble on Tim's stiffening cock. I licked and bit it lightly. Then I leaned into his crotch and nuzzled his smooth, heavy sack with my nose, tenderly kissing Tim's inner thighs. He caressed my cheek and moaned his enjoyment.

I broke off my affections and hooked up his other stocking. With both stockings attached, I took the sheer panties, held them out in front of my face and admired the wispy material. I couldn't wait to see them hugging his bum and balls. I knew they couldn't possibly hold Tim's now fully grown panty snake. I lowered them allowing Tim to step into them. Once in, I pulled them up as Tim remained silent. Again I kissed his bobbing head before I slipped the sheer panties to his waist. The front covering his sack but hung under the base of his ten-inch boy bone.

Reluctantly I left my favorite food, cock meat. Rose to my feet and held up his sheer bra. Tim slipped his arms through, turning away as I hooked him from behind. We were both now dressed for our evening.

Not being able to wait any longer, I dove onto the bed and began to push the remaining lingerie off the bed, onto the floor. I reached for the pillows and piled them beside me. I didn't know what position Tim would have me in. So I wanted to be prepared.

I lay back on my elbows and said, "Ok Timmy, I'm all yours."

Tim stood at the foot of the bed looking hard and sexy. His ten-inch sword throbbed with each of his heartbeats. As he leaped onto the bed beside me, he said, "No, I'm all yours."

I smiled and he nervously smiled back. While we lay on the bed, I reached for his hard boy bone. I gently stroked him for a couple minutes, we both knew after tonight Tim wouldn't be a virgin. Without saying a word, I rose to my knees as Tim rolled on to his stomach. We both knew our roles. I was now the man and he was the girl. I crawled in between his legs as he raised his hips up. Since Tim's legs were longer than mine, He tucked his knees under himself to get his pussy level with my sissy cock. I reached under and pulled my cock to the side of the teddy crotch. My hand then went to his cock, teasing it as I gabbed the bottle of oil. Before pouring oil into my hand, I stretched his panties to the side. Gently I applied oil to his bum hole then to my cock. Before I entered him I poured some oil on my finger and slipped it in slowly. After a couple strokes, I removed it and added more oil to my cock head. Placing a hand at his waist, I moved forward until my cock head was bobbing at his greased rosebud.

Holding my girly cock in my hand, I pushed my hips into Tim's cheeks. With a deep breath, I watched in fascination as the head disappeared. I was surprised how quickly it went in. No resistance and by Tim's soft groans, no pain. Suddenly I was completely in. Tim let out a gasp and buried his face in the pillows.

He turned his head sideways and said, in a deep voice, "Fuck me hard. I want it like a girl."

This caught me by surprise. I didn't expect Tim to demand to be fucked like a sissy. But I wanted to please him, so I began to slip out then back in. Slowly at first, then steadily building speed. I was groaning and moaning, loving the feel. My four-and-a-half inch dick was gliding through his pussy hole like a small steam piston. I felt that he wasn't get a great fuck because of my sissy size. If my cock was at least six-inches, like Rob's, he would've probably enjoyed it more. As I rammed him with all my strength, I thought back to our night at my house, when Tim asked if I knew of anyone else who might want to join us. At the time I told him no. But Rob might have been willing to fuck us both if he hadn't swore off man sex since then. It could've been great to get the two guys who enjoy fucking me together at one time. I often wondered what a gang bang would be like.

I came back to reality when Tim moaned into the pillows and began to push back meeting my thrusts forward. We were both near our limits. My cock felt as if it had grown twice its size. But Tim's ass was so loose that it only lightly gripped as I slid out and in.

To reach our climax, we needed to buildup more friction. So I pulled out without warning. As Tim moaned loudly and looked back at me, I quickly wiped my cock off of oil and reentered him. As my dry head started in it felt tighter. I could feel more pressure around my shaft. Sensing I would shoot soon, Tim wiggled a bit, adjusting his bum for the final assault. Gripping his waist, I began a hard, steady rhythm. I laid into him with all I had. My balls were aching to release. Tim moaned like a slut. Yelling to "fuck me harder, harder." With my juices ready to blow, I rocked back and forth, slamming myself into him.

Without warning my balls exploded. I started to spray Tim's innards with my hot milky goo. Tim let out a low moan. It also sounded like he started to cry into his pillow. I began to whimper. The release felt so wonderful. I continued to work my sissy cock in and out until my blasts turned to weak spurts. As I enjoyed the lust of fucking Tim, I also couldn't wait for Tim to return the favor. Now I want to be fucked. I didn't want to pull out to soon so I slid in once more than held tight inside. My hands locked on to his hips. I ground my pelvic into Tim's ass getting as much sexual satisfaction as possible.

Tim lifted his head out of the pillow and softly said, "That was so fucking great. I want to do that again."

I replied, "Oh, we'll do it again, but not right now. If I have the strength, we can try later." As I tenderly rubbed his lower back I said, "I think we need another cock."

Tim nodded his head in agreement saying "That would be perfect."

Sensing we needed to relax for a few moments, I eased back from Tim. My cock popped out. Coated with both oil and cum, I leaned onto my heels and wiped off. Then I dabbed his bum hole, cleaning the mix that oozed out. Tim stretched out his legs and slid down onto his tummy. I jammed the towel in between his cheeks, then got out of bed and went to the bathroom to clean up. I brought back a warm, wet, cloth to wipe Tim. Spreading his bum to clean the mess, Tim barely moved.

Once cleaned, I tossed the cloth aside and lay down beside Tim. With my hand on his bum, I lightly caressed his tight cheeks. Tim lay quietly with his eyes closed.

I softly asked, "How was it really?"

He smiled and in a whisper said, "That was so good. You WILL fuck me again."

I said, "You won't have to ask. I'll be glad to. Do you think you can pleasure me now?"

He opened his eyes and smiled. I knew that meant yes. I rolled on my back as he slowly rose up. Tim told me to stay on my back. He then straddled my thighs. His cock was at full length poking into my crotch. I stretched to touch his cock, but Tim leaned down, lowering his face, blocking my advance. I just lay back as his warm mouth moved to my chest. He began to suck on one of my boobs through the material. After a minute he began to undo the buttons at the top of my teddy. Now open, he had access to suck on my naked nipples. He nibbled on each tit. Alternating between them. This was driving me crazy. I wrapped my arms around his head drew him down, smothering his face between my breasts.

After a minute, I released him. He continued to bite and suck until my nipples were tender. Tim's tongue and mouth must've gotten sore because he stopped, then slid down until his face was above my sissy cock. Thinking he was going to chew on my cock, I prepared myself for more sucking. Instead, I suddenly felt a hand reach in between my thighs and pull on the crotch snaps. When the snaps released, the front panel recoiled up to my tummy while the back slid up the crack of my ass. I was exposed to Tim's oral desires. Tim leaned back grabbing my waist. Then lifted me up with little effort, allowing the material at my ass to slip past. He lowered me back down. The ease at which Tim seemed to lift me came as a surprise. I knew now that Tim was more powerful then I had thought. I played the submissive during our times together because I liked the role. But now I knew if Tim wanted to, he could make me do anything he liked. I felt helpless lying there. But it was a good helpless feeling.

Tim then lowered his face down again, drawing my cockette into his mouth. His tongue swirled over and around my head and shaft. As he ate me hard, he made slurping sounds. He sucked so hard that I thought he was going to suck my cock down his throat. I was sure I would soon be a real girl.

We couldn't hold back our emotions any longer. I let out a long low groaned. Uncontrollably raised my knees, squeezing Tim's head between my thighs. As Tim worked me over, he groaned deeply from the pleasure. We both just let go of our emotions.

I cried out, "Stop it. Fuck me now."

Tim stopped dead. Lifting his head, without a word he sat up. Raising my legs out from under his bum. He propped them up against his chest, reached for the oil and towel. Meanwhile, I raised my hips and pushed a pillow under my backside.

I tried to relax as his oily fingers touched my bum hole. His other hand held the oil as he leaned onto my legs. My ass rolled up off the pillow. Tim poured oil into my crack and began to finger my pussy. As he forced my legs farther forward, Tim's cock head tapped at my sack. One slick finger slipped in quick and easily. I whimpered when it was all the way in. He pulled out, added more oil to my hole, than drove back in again. And I whimpered again.

I mumbled, "Oil up and fuck me. I can't wait."

He withdrew his finger and applied oil to his cock head and shaft. I impatiently rocked side to side unable to wait calmly. As he oiled up that beautiful piece of male meat, I grabbed my calves and drew them tighter to my chest. Giving Tim complete access to my pussy. Tim shifted his body, aligning his head at my opening. I took a deep breath as Tim leaned into me.

His face inches above me, he whispered, "I've been waiting for this all week. I'm going to fuck your brains out."

I just smiled and let out another whimper as his head pushed through. I wanted him buried to his balls now, but was glad he slid in slowly. Accepting his length would take a bit of stretching. He pushed past my sphincter. The first six-inches slipped through without resistance. It was the last four-inches that took a little more effort. I was moaning with every inch that it drove in. Feeling some discomfort, I lifted my hips, making his invasion a straighter shot. Slowly Tim filled me with his man pole. When his thighs hit my ass, I was relieved that he was all in. I couldn't take another inch or I would've fainted. It felt like a Great Dane fucking a Cocker Spaniel. I felt a tear coming on. Tim saw my eyes water up and held still for a moment.

I let out a low growl, wiggled my ass, than told Tim, "Go ahead. Fuck me hard."

My knees were above my shoulders. Tim's face was above mine. Lifting his hips up, he pulled his cock out three-quarters of its length. Then groaned out loud as he buried himself deep in again. Soon he began a smooth, steady rhythm. We both were ready for the ride. I couldn't wait to have him pound my ass.

I closed my eyes and began to moan uncontrollably as Tim picked up his pace. He used all of his length in me. Tim's sack slapped against my ass as he worked me hard. I asked for it and he was giving it to me.

After minutes of slamming me even harder than before, Tim's steady rhythm began to become erratic. He was nearing his release. Tim tried hard to keep under control but his balls kept sending him signals to start shooting. I meanwhile was near passing out. Suddenly he leaned his face down, giving me a long, wet kiss. I was trapped between my legs and could only lie there and accepted his passion.

As we kissed, Tim's first blasts of cum shot through his cock. While Tim pumped cum into me, he forced his long tongue past my lips. It felt like a wet piece of meat slipping to the back of my tongue. I just knew it would slither down my throat. That was more than I could handle. I was getting the hardest, longest fucking of my life, and being french kissed with a snake. I couldn't handle it any more. As Tim's tongue swabbed my throat, I began to lose control over my emotions. But Tim's attention was still on emptying his balls into my boy pussy. I could feel each shot being injected into my sore stretched ass.

His tongue felt like it was lapping at my tonsils, slipping over and under my tongue. He was probing me from both openings. I had as much of him inside as I could take. A tear started to run down my cheek. I moaned and whimpered. Tim had not yet sensed my emotional breakdown as he was focused on fucking me silly. And that's just what he did. I began to cry in his mouth, like the sissy I was.

Tim raised his upper body, pulling his long tongue from my mouth. He braced himself up, holding my legs down. With all his strength, rocked into me three more times. They were hard and deliberate strokes. With the last stroke, he pushed in and ground himself into me. This signaled he had finished his assault on my poor asshole.

Still with my legs overhead, I let go and began to cry openly. I wept from sexual overload. Through my tear filled eyes, I looked up at Tim to see his reaction. I thought he might be annoyed by my girly emotions. Tell me to shut up. Instead he looked down on me and asked if he had hurt me.

Sobbing as I wiped my eyes, I whispered, "No. I don't know why I'm crying. I guess from pleasure."

He smiled and leaned down. His face inches above mine he said, "In that case I should be crying too. That was so great."

He was still inside when I passed out for a few seconds. When I came to, I felt him tenderly kissing my cheek. I opened my eyes and smiled. After a couple more soft light kisses, Tim leaned up off my legs. I lowered them on either side of him with my knees bent up. He stayed inside. I was full but content to have him remain there. Tim asked if I wanted him out.

I said, "Not yet."

But he started to withdraw. It felt like a pole being removed. When he was completely out, I let out a sigh. His cum soon followed. It leaked out, down my crack and onto the pillow and bedcover. Tim wiped himself then began to dab at my seeping bum hole. At that point, I was completely drained. While he cleaned me, I nodded off again.

In my dream like state, I sensed Tim laying down and snuggling up against me. His arm lay across my chest. We both must've drifted off. A while later, I awoke and looked over at Tim. He was in a deep sleep. His five-inch soft cock resting on my thigh. Not wanting to leave, but knowing it was probably getting late, I checked the clock. It was going on one a.m. My junior license limited me to driving until midnight. With the little energy I had remaining, I quickly sat up, waking Tim in the process.

He asked, "What's wrong?"

I said, "I need to get going. I should have left an hour ago."

He leaned up, propped by his arm and said, "I thought you were going to stay over."

I said, "I don't think that's a good idea. What if Sue comes home early?"

He sat, thought for a couple seconds and nodded he understood.

I slowly slid off the bed, now feeling the full affect of our evening. I was sore and stiff. I gingerly picked up my things, stuffed them into my bag. Snapped the teddy at my crotch then pulled on my pants and stuffing my shirt in the bag. I would drive home with my teddy exposed. I hated to leave so fast but I didn't want to lose my license. Tim asked if I wanted him to drive me home. I said that I was fine. I grabbed my bag and headed towards the door. Tim followed only in his undies.

As I opened the door he whispered, "Too bad you couldn't stay. I would've liked to cuddle a little longer."

I softly replied, "Maybe next time when I can stay longer. Bye."

I stepped through the door and headed to my car. Tim stood in the doorway until I drove away. While driving, I felt my ass leaking into my pants. The whole way home I drove with a smile on my face.

As I pulled in our driveway, I saw Rob's van parked next to the house. I was a bit surprised that he would be home. One-thirty was an early night for him. I saw only a light on in the kitchen. I grabbed my bag and quietly went in the kitchen door. Expecting Rob to be up, I was relived that he wasn't. I didn't want him to see me still in my teddy. As quietly as I could, I stopped at the bathroom then went into my bedroom.

In my room, I dropped my bag next to the bed, then quickly stepped out of my pants and crawled into bed. I let out a sigh and closed my eyes waiting for sleep to take me. But just before I drifted off, my bedroom door slowly swung open. A shadow of a figure formed from the kitchen light, walked through the doorway. In my groggy state, I could just make out that it was Rob, naked.

He said in a low voice as he closed the door, "I hope you aren't too fucked out."

I didn't say a word. I was just hoping it was a dream. Any other time, I would've loved to have Rob fuck me, but I was worn out. Tonight though, Rob wouldn't take "no" for an answer. I reached to turn on my table lamp as Rob stepped next to the bed. His hard cock bobbing inches from my face. As I lifted my head to accept his gift I prayed for strength.

I'll write soon about Rob fucking my already well stretched asshole.