She had made the bed with new sheets and laid out my red babydoll chemise, which was crotchless. She had also gotten out my black leather wrist and ankle cuffs with the matching choker. I looked at it all and then at her. She was positively giddy with excitement, so I had no choice but to get dressed for her. When I was done, she ran out to get John, but I hadn’t noticed the blindfold she had in her hand.
While I was waiting, I looked around and saw she had moved a chair close to the bed. I assumed that was where she planned to watch from. She was really excited about this, but so was I. Even back when John and I were just suck-buddies, I had wondered what it would be like to be taken in my ass. I masturbated using dildos and imagined it was John’s cock in me. I always came harder during those times. I just never dared to tell him what I really craved.
DeeDee opened the door again and led John in by his cock. He was blindfolded and naked. She stopped just in the doorway.
“John, stand here for a second,” she told him.
She took me by the hand and directed me onto the bed. She had me get on all fours, my ass up like we did when she was going to peg me, and then she put a blindfold on me. Again, I hadn’t seen her pick up the blindfold, which made me wonder if she had gotten anything else out of our toy chest. Then she got back off the bed. I couldn’t see anything, but I heard her talking to John.
*****
“You ready, John? Come with me, I’ve got a little sissy ass for you to have fun with.”
I led John to the bed behind Will and took off his blindfold. The first thing John saw was Will’s ass pointing invitingly at him. All dressed up in his little sissy outfit.
I looked over at John and said, “That’s my little sissy’s ass, and you can borrow him as long as you fuck him like you fucked me last night. Hope you like the red outfit. I dressed him just for you, even made sure I got a crotchless outfit for easy access to his cute little hole, just waiting for that big swollen cock of yours.”
John was already hard, so I pushed him towards Will as I patted his naked ass. He climbed up behind Will. When he got close to Will, I lubed his massive erection and used two full lube applicators to fill Will’s ass. I hoped it would help Will take John’s enormous cock easier. I placed one hand on Will’s thigh and lined up John’s cock. As soon as his cock touched Will, he thrust forward and sank deep into my Will. I barely had time to get my hand out of the way. John held Will’s hips tightly and kept his cock buried, just like he had done with me last night.
Watching John push into Will so hard and fast reminded me of him entering my pussy. The thought caused me to cum, remembering how it felt the first time. For a second, I felt bad being so excited watching Will being violated, knowing it had to be painful. But ever since the first time he asked me to peg him, I’d wondered what it would be like to watch him actually being fucked by another man. As I sat in my chair to watch my two sexy men perform for me, John started pumping into Will, slowly at first. Watching him slide that big cock made my pussy ache, wanting Will in me at the same time.
I was so excited to watch them, my pussy was dripping wet. I wanted to reach between my legs and tease my own cilt, but I wanted to wait. Just getting everything ready and seeing John penetrate Will’s ass for the first time, I had already had my first orgasm of the night. My legs were trembling; I was so excited watching that I was already getting close to cumming again. Watching my boys fucking was more exciting than I expected, but sitting here alone started feeling wrong. I needed my Will, I wanted to feel his touch.
After a short while, I finally carefully climbed onto the bed in front of Will. I sat there watching them both, amazed at the look on both their faces as they were both lost in their passion. Seeing them both enjoying this only made me hotter. Suddenly, Will pushed back hard against John. I saw a flash of pain race across Will’s face, then his expression changed to pure ecstasy.
I came hard watching this. John hesitated, but Will encouraged him to continue. Will was softly moaning and matching John’s movements. I waited, listening to Will encouraging John to continue, watching them work together as John fucked my Will. I had to have Will, too, so I removed his blindfold. My legs were spread wide to invite him to take me; my wet vagina was aching to feel his touch.
*****
As I waited there blindfolded, with my ass up waiting to be fuck by John’s monster of a cock, I was so nervous my body was actually shaking a little with anticipation, or was it fear? I felt John climb onto the bed behind me. I didn’t know how close he was til he grabbed me by my hips. Then I felt DeeDee by my side, too. She inserted a cold tube, which I assumed was lube, just like we did when she pegged me. Then she added a second tube.
Next thing I felt was John’s hands had me in his firm grip, and my asshole was on fire with his massive cock stretching it out more than any dildo I had ever used. He did the same to me as he had with DeeDee, pushed his cock as deep as he could, and held it there. I felt so full with his enormous, hot cock inside me. The pain faded fast, and I started to relax my muscles. Guess he felt me relax, because as soon as I did, he began.
John was sliding his cock back and forth inside me. I could feel the head of his cock close to my opening, but it never came all the way out. He had perfect control, stopping at just the right place and pushing back in. He continued this slow rhythm, using my ass to stroke his wonderful, hard cock, while still holding onto my hips. The slow rhythm of him pumping his cock in me felt amazing. I found myself pushing back on him, trying to match his movements. He started to move a little faster as I began to moan from the pleasure quietly.
The blindfold forced me to concentrate on his movement, to picture him behind me, holding my hips and pumping back and forth as his cock continued fucking me. I never expected it to feel this good. It was better than riding any of our dildos. It was even better than getting pegged—a totally new and sensual experience.
I didn’t want him to stop. I wanted more; I wanted him to go faster, harder, deeper. I raised my ass a bit higher, and on his next push forward, I rammed my ass back till I felt his balls slap against me. As I did, my own dick slid across my thigh, and I felt a drool of precum run down it.
Rocking back like that really hurt, and my ass tightened up around his cock. He must have felt it or heard me cry out. He pulled back as if he was going to pull out. So I pushed back against him again. I wasn’t about to let him stop now. Even with the pain, it was bliss having him inside me finally. I needed him to cum, to fill my ass with that warm cream.
“Don’t stop,” I managed to get out between breaths.
I was breathing so hard, all I could do was moan; I was getting louder, too. I was actually close to cummimg myself and had not touched my cock even once. I managed to get my breathing close to under control and was able to say a bit more to John.
“John, your cock feels so good inside me. Fuck me like you fucked DeeDee last night.“ I gasped, trying to take in another breath of air. “Treat my ass like you own my pussy. I want you to pound your cock into me and feel your balls slapping against me as hard as you can.” I took in another breath between words. “Just don’t cum yet. I don’t want this to end, not yet,” I begged.
My breathing picked back up; I was taking in deep breaths every time he pushed in me. Looking back, I realized I was taking my breaths in rhythm with his thrusts. As he drove in hard, I took a breath; as he pulled back, I exhaled. The faster he went, the quicker my lungs worked. Then I felt it: he reached that point where he could not control himself anymore.
Just like with DeeDee, he stopped holding back and started pounding into me. That’s when I realized DeeDee had lied all along. It did hurt, but a different kind of pain. A deep, erotic, primal pain sent shockwaves of ecstasy flooding through me. I could feel the wave of pleasure roll from my head through my body and down my legs.
Suddenly, I could see again. I didn’t know when DeeDee had moved, but there she was, sitting at the head of the bed, right in front of me. Her legs spread open so her beautiful flower was directly in front of my face. The moment I saw her, all the pain was gone; John pounding my ass was background noise. All I could think was that I wanted her to move closer. Her face was red, she was breathing as hard as I was, and her body was covered in sweat. I could see her pussy was very wet, practically drooling. I knew she had already cum at least once, maybe more.
I wondered if she had been masturbating while watching from the chair, or had she done it while sitting in front of me while I was blindfolded? It didn’t matter; I could smell her sex and wanted it. I wanted to taste her, but I couldn’t reach out; all my weight was on my arms holding my ass up so John could keep pounding into me. She must have seen the want in my eyes, as she slowly slid forward, closer and closer until her pussy touched my face.
I wasted no time and dug right into her wet, open flower. I completely forgot that John was still driving his monster cock into me like he was trying to split my ass open. All I could think about now was how DeeDee tasted and smelled. Her thighs held my head right where she wanted me, and I got to work on her sweet little clit. I was right about her having already come at least once; I knew that taste and smell of her sex. But I wanted to feel it myself, to feel her orgasm flood through her. But she wanted something else first.
She put both her hands on the back of my head and held me even closer to her pussy, slightly raised so I could get deeper. She was trying to get my mouth down there; she wanted my tongue inside her. I had to give it to her after all; it was she who gave me this incredible fucking I was taking.
John hadn’t missed a beat and was still going strong. I just knew he had to be staring at DeeDee’s soft, inviting body: DeeDee’s firm breasts with her hard nipples pointing at him, waiting to be sucked. I was sure I felt him driving harder and faster into me because of DeeDee’s luscious body right in front of him, begging to be next.
All three of us were breathing hard, lost in passion. I slid deeper and began to explore the depths of DeeDee’s vagina. As soon as my tongue broke through and started exploring deeper, her legs closed in on me. She tightened her hold on my head as she finally came again. Her legs pinned on both sides of my head were shaking; her orgasm was intense and not letting up. Her legs covered my ears, but I could still hear her muffled voice as DeeDee called out as she came.
“Don’t stop, don’t either of you dare stop,” she ordered. “John, cum with me; fill Will’s ass the way you filled me last night. I want to see your cum oozing out of him.”
I felt John lurch hard into me as he buried his cock as deep as he could. I felt DeeDee’s vagina trying to clamp down on my tongue as her orgasm continued to ravage her body. Then John’s cock exploded. I could feel him hold it in me, as he had in DeeDee, his cock pumping sweet, hot cum into my ass. Wave after wave of heat washed through my body as I felt them both at once. Then suddenly, without ever being touched once, my cock let go of its load and joined them.
We all let out a gasp of air as we were overcome with the most intense orgasm I’d ever felt. It was like it flowed from DeeDee to me and then to John, and back again. I didn’t think I’d ever cum that hard before. I felt DeeDee reach over me and pull John forward. I knew she was kissing him passionately. His cock was still buried inside me, still slightly hard, just enough to stay where I wanted it. I wasn’t ready to have him pull out, not just yet.
But DeeDee had other plans; when she was done kissing John, she grabbed me and pulled me up so she could plant her face on mine. Her tongue jumped into my mouth, and when it left, she sucked mine into her mouth. She held me there, mouth to mouth, as we started breathing for each other; she took a breath in as I exhaled, and back to me. It felt like we had become one person. Seemed like we were like that forever, but I’m sure it was only seconds. At that angle, it wasn’t long before John’s cock vacated my ass hole.
Cum was dripping out of me from everywhere, leaking out of my cock. John’s cum oozed out of my ass, and then there was DeeDee’s sweet nectar still covering my face. That was all I was to both of them at that moment, a depository for their spent sex, and I loved it. This had been one of the best experiences I’d had; first times always were. And having my DeeDee there with me made the wait so worth it. Her being there added to the excitement and passion. I loved her more every day.
I rolled over onto my back to catch my breath, lying in my own cold, wet spot that my cum had made. John collapsed next to me with his warm, sticky cock pressed against my leg and one arm over my chest. It was paradise. I just needed my other bookend to make everything perfect. DeeDee joined us seconds later, snuggling up to me. As her warm, soft breast pressed against my arm, she also put her arm across my chest, right next to John’s. We lay there, all of us still gasping for air, still feeling the final waves of that fantastic, incredible orgasm.
Once again, we found ourselves exhausted, in a pile of sweat, cum, and tenderness.
{Next: Chapter 5, DeeDee had another surprise for John’s last evening.}
