This is 100% true story and a very fond memory. 28 yrs have passed so I am ok with talking about it now and sharing this amazing experience with y'all.
Sierra is this amazing trans woman that I met in the mid 90's and had a wild relationship with. At first it was just lust and it turned out to be an incredible love in my life.
I want to preface this next part by saying that I am very protective over my family, friends and the people I care about. This will come to play later in this story. This is all true, I am not exaggerating or making anything up about this incredible woman and the time we spent together. Me, telling this story is my way of reliving and sharing the beautiful time we had together.
When I left that morning, I felt warm and cared for. Sierra and I were really becoming intimate and not just lustful. When I wasn't with her, I was thinking about her. I never thought I could feel this way about anyone but a biological female. But, I was and I felt weird in a way and so comfortable in another way. She did things that showed me that she cared like making breakfast and my lunch and then coming to my work and basically marking her territory, lol. BUT, some of her comments or lack of comments still had me curious about her past.
All day Wednesday I was a little nervous on how that evening was gonna go, I wanted more than anything to hold her in my arms but the conversation ahead was going to be difficult for her. Mid-afternoon she hadn't stopped by work so I took that as she was still at my house. So I called my home phone (this is the 90's, lol) and the answer machine picked up and I said babe you there and then she picked up the phone. We talked for a moment and she told me she ran home to get clothes and toiletries and came back. She said she was just watching a movie on the couch. I told her that I would skip the gym today and I would be home around 530 and would bring dinner with me. On the way home I stopped at Popeye’s and grabbed a bucket of chicken and drinks.
When I arrived home, I ran up to the apartment and used the bathroom and told her to get a dress on or some clothes on that we were gonna go down to the park on the intercostal for dinner. It was a beautiful evening with 75 degree weather and a slight breeze, and the humidity was low that day.
When she was ready we drove about 2 miles down the coast to the park. We went down into the park and found a picnic table right next to the water. We sat and watched a couple dolphins and manatees in the water while we made small talk. Eventually she couldn't hold it in anymore and asked me what I wanted to talk about.
I kissed her and held her tight to me and told her that she was safe with me and could tell me anything that we all had a past and we had to accept that in order to move forward together. She just looked at me and her eyes began to get watery. I wiped her eyes and told her that she was safe again and didn't need to cry. She took a deep breath and turned back to the water and just sat there for a moment in silence. She told me about her teenage years and knowing that she was gay and felt more comfortable as a girl than boy and at first her dad didn't really accept her. He wasn't ugly with her but wasn't accepting of it. She said that her father is a little better now but still has a hard time with it. She proceeded to tell me that she had met an older man that had money two years ago and he fell in love with her and offered to pay for her transition surgeries.
She had been with him for the past two years up until a couple months before I met her. She left him because he had become to controlling and mentally abusive. The only time she was allowed to leave the house was when he was with her and she could only see her family once a month. She said that she snuck out of his house one day and never returned and her parents set her up with the apartment here in Cocoa Beach. She said this guy was in his 50's and had millions and had an ego from hell and she had to leave regardless of the money.
I sat there listening to her, getting more and more upset and protective of her. I asked her if he knew where she was and she as far as she knew he did not, but she always is nervous and looking over her shoulder. Tears are running down her cheeks the whole time she is telling me this story which only made me more upset. I took her face in my hand and turned her to me, and wiped her cheeks with my palms and held her face and kissed her ever so gently. I promised her that I had her back and she would always be safe with me.
Sierra knew very little of my background except that I was former military. She never knew the violent side of me, she had never seen me get mad or in a fight. I had to explain that part of me to her in terms that she understood and that she had no reason to fear me, but I wanted her to be aware of that side of me. She still had this "not quite sure" look in her eyes so I told her to hold my hands and take a good look at them. When she did, she saw that my knuckles had scars in them and some of my fingers were misaligned from fighting, and then her eyes showed understanding. She leaned in and said thank you and kissed me deeply.
We sat there in the park until after 10 pm and just talked and held each other. It was actually the cops that kicked us out because it was getting late. We went back to my apartment and fell asleep together.
More Too Cum....
Pt6
After the talk, the week went quickly. We were together every evening, either at my place or hers. The weekend came and went. She would stop by my work somedays and brought me lunch; some of the guys in the office were envious and always asked me how I landed that, I just laughed them off. Things were going great, the sex was incredible and for the first time in a long time I was happy, even though I hadn’t had any pussy in weeks. Early the next week Sierra told me that she needed to go back to Orlando to see her mom. We talked a lot about her being safe with her ex still around and not knowing if he was looking for her. She re-assured me and she took off for a couple days.
While she was gone I had an idea to get away that weekend up to St. Augustine. It would be a great opportunity for us to get out during the day and visit the fort and the beaches. I found a decent 3 star hotel near the fort that I could afford and made reservations for Friday and Saturday night. I also made plans for us to have a picnic at the fort on Saturday.
Not having her around each night was weird and not having sex made me break out the box of toys and handle my own business a couple times. Every day, she would leave me a message on the phone that she was safe and with her parents, which made me feel better. On Wednesday, she left me a message letting me know she was safe but she was going to visit some friends and she was coming back on Thursday morning to Cocoa Beach. I was happy that she was seeing her friends but was worried because her ex knew where they hung out.
Mid-day Thursday my beautiful ebony queen comes into my work shaking her ass all the way in wearing a new dress. My co-worker whispered "fuck you" to me as I got up, I turned and patted him on the shoulder and went to her and gave her a kiss. I whispered, "You ok?" and she shook her head yes, and said she doesn't think she saw him or anyone he knew. I was relieved and told her to go home and relax and I would be by later that I had some good news to tell her. She gave me that sexy devilish grin, kissed me and walked out. After work and the gym I headed to her apartment to take a shower and spend the evening with her.
When I arrived she opened the door in a set of silk night pants and tank top that were rose in color with no bra or panties on. I didn’t even wait to get in the door to pick her up and kiss her. She laughed and told me to put her down that I was all sweaty from the gym and to go shower, lol. As I went in I could see her nail stuff spread out all over the floor, what I didn’t see right away was that she was cleaning and painting her toes and fingernails. I proceeded to the shower and put on some shorts that she let me keep there. We ordered Chinese food for dinner and just lay on the couch holding each other watching a movie throughout the evening. When the movie was over, she sat straight up on the couch and looked at me and said “Didn’t you tell me you had a surprise for me?” I chuckled and sat up as well. She straddled me and put her hands on my shoulders with this childish anticipation, wiggling and being excited to hear what it was. I told her that we were going to St. Augustine for the weekend and we didn’t have to hide and I had a few things planned while we were there. This got me a very sensual deep kiss and I could feel her cock grow between us and this kicked mine in as well.
I told her that I missed her this week and she gave me this loving smile back as she pulled her top off. I kissed her soft sweet lips again and then made my way down to her neck which caused her to moan and hold my head as I kissed down her neck to her shoulders and to her firm breasts. My hands caressed her ass and back as I sucked on each nipple and lightly bit them. Her nipples were perfect to me. Her areolas were a little larger than a quarter and the actual nipple was thick like the tip of a pinky finger. I loved them. After a few minutes of this she stood up and took her silk pants off and my shorts and straddled me again. Our cocks rubbed together as we continued kissing and petting each other. Both of us had precum leaking everywhere. I told her to stand up on the couch and turn around. She did as I asked and I pushed her feet apart and pulled down on her hips placing her ass right on my face. I bit her ass cheek and then slid my tongue right into her tight little hole. She let out a loud “OH Baby” as I began my tongue assault on her rosebud. While I was licking her, I wrapped my arms around her legs to help hold her up and I began stroking her cock with long strokes making her involuntarily buck her hips on my face. After about 10 minutes of this she blurted out “OH Baby I am gonna cum, don’t stop!” I pushed her up and pulled her cock backwards into my mouth and began sucking the head of her cock and swirling my tongue all around her thick spongy head. Moments later her legs began shaking and she let out this loud moan and I felt her stiffen up in mouth and then she unleashed 4-5 heavy shots right down my throat. I continued to suck her until she was soft and couldn’t stand anymore.
She slid down my chest and onto my lap. She immediately felt my raging hard on underneath her, I lifted her hips up and slid my cock with one slow push deep into her ass. We both moaned as she rocked her hips back and forth as I pulled her ass cheeks further apart letting me into even deeper. She lay back onto me as she continued to grind her ass onto my cock. My hands continued to caress her thighs, stomach and breasts as she rode me. I cupped her breast in my left hand and reached around began stroking her cock with my right. It didn’t take long for her massive cock to get hard again. I lost track of how long we stayed like this but it was like we were one body. We were sweating and caressing each other as my cock was buried deep in her. She would turn her shoulders far enough so we could kiss without stopping what was happening. I finally couldn’t take anymore and I whispered in her ear that I was going to cum. I held her close to me and was still stroking her cock and pinching her nipples as our pace increased. I knew she could feel my cock get harder right before I came in her and it must have sent her over the edge again as well, because as I was filling her, she unleashed another huge load all over her belly and breasts.
My cock just stayed in her for a few more minutes as we held each other trying to catch our breath. I ran my fingers through her cum and tasted it and then did it again but kissed her with it in my mouth. She begged me not to move but we both needed a shower and I needed to go home. We showered together and washed each other until the water turned cold. I gave her a kiss and left.
The next day I was taking a half day at work and she showed up around 10am to get my apartment keys. She was always in these spring dresses that drove me wild, nevertheless I managed to finish off the next few hours at work, before I raced home.
More to cum…
Sierra pt 7 – The Vacation day 1
I got home from work shortly after 1pm and Sierra was almost asleep on the couch. I kissed her forehead and told her that a nap was a good idea before we left and I went and lie on the bed and set an alarm for about an hour later. Sierra came and lay with me and before we knew it the alarm was going off. I got up and left her in the bed seeing that she was already packed. I jumped in the shower and washed up. While I was in the shower Sierra called in and asked what suitcase I wanted and she would get it out for me.
I finished up and came back into the bedroom where she handed me a pair of women’s underwear, a silk t-back and a two piece cock ring. Neither of these was mine so she had to have bought them while she was away. The two piece cock ring first went around both my cock and balls as a normal ring would and then the second part was about an inch wide and acted as a spreader/ restrictor that went around the scrotum between the balls and cock. Sierra helped put it on me and it felt tight at first but I got used to it. Then she handed me the panties and I put them on. I wasn’t quite sure where she was going with this but I did as I was asked. She then looked at me and said there was one thing missing. I looked at her inquisitively and she turned around and grabbed my black box of toys. She reached in and began digging around until she came out with a small ass plug. She told me to turn around and bend over. She spit on the plug and rubbed some spit into my hole before she inserted the plug. I was hers at that moment. My cock and balls were restricted and I had a plug in my ass all being held in with a silk thong. I had no idea where this was going but I played along. She told me I could get my shorts and shirt on now and I couldn’t wait to find out what she had in mind for later.
The hour and a half ride to the hotel was interesting. By the time we left it was late afternoon and in the heat of the day, mind you this is Florida and it was over 100 degrees out. Sierra decided when we got out of town that we needed to “relax” a little bit more. She told me to pull the car over and I did, then she told me to take my shorts off. I did as I was told and as I took my shorts off she untied her cock and let it hang free and then untied the front of her dress and pulled her breasts out. She told me to start driving again and not to worry about anyone else that might see. As we drove, she began to play with her nipples and stroke her massive cock. Trying to watch her and concentrate on driving was difficult. As cars passed us, some saw her playing with her nipples and would try to watch but never saw below the window line to see that massive ebony cock of hers. Nor did they see me in panties and in a cock ring and stretcher. My cock was rock hard and balls were swollen watching her and the excitement of being so exposed. After a while she stopped playing with herself and she began teasing me.
Sierra leaned over and pulled the thong to the side fully exposing my cock and began sucking the head of my cock and massaging my balls making them swell even more. She took my cock out of her mouth and began to rub my head in the palm of her hand as she massaged my balls in the other. It was everything I could do to keep the car on the road. A few minutes later I was almost about to blow a huge load when she smacked my balls making them hurt. She then reached between my legs and began twisting the plug in my ass. It had been gently pushing on my prostate the entire trip and now she was twisting it and wiggling it inside of me. It was almost unbearable, I was leaking precum like a faucet but she refused to let me cum. About, 20 minutes before we got to the hotel she told me to pull back over. I did as I was asked and when I put the car in park, she pulled my right leg up and reached under me and without warning pulled the plug out of my ass. It almost sent me over the edge. She told me to get out of the car and put my shorts back on. I was scared to get out of the car with other cars going by, but she smacked my swollen balls again and repeated herself. I reluctantly got out of the car and went to put my shorts on. As I bent over to pull them up I got a few honks from passing cars before I got back in. When I got back in, she was all tucked up and her breasts were back in her dress.
When we got checked into the hotel and into the room, I grabbed Sierra by the arm and pulled her to me and kissed her. She giggled and pushed me off and told me that she wanted to try something and that I had to be patient and do what she asks without question. I gave her an inquisitive look and she just said to trust her. We unpacked and went to a small café for dinner. After dinner we walked down to the Fort to see the sunset and sat on one of the benches holding each other. My cock had been restricted all day and it was getting to be unbearable. I whispered in her ear that it was hurting and she reached up my shorts leg and began to pull it off. The ring came off relatively easy but the stretcher on my balls wasn’t, I had built up such a load that it wasn’t coming off very easily. She looked around to see if anyone was in the area and there wasn’t anyone close, so she unzipped my shorts and pulled my cock and balls out. This allowed her free access to stretch the ring over my balls and take it off. The relief was amazing. She massaged my cock and balls in the palm of her hand for a minute and then put me away. We sat for a while longer until the sun had gone down before we walked back to the hotel. It felt great to be out in public not having to worry about anyone I know finding out our secret.
At the hotel, we got in the elevator and she told me to undress. I looked at her like she was crazy and she told me that I promised to obey. I took off my clothes minus my sandals and she put the cock ring back on me with the stretcher. My heart was pounding that the hallway would be empty when the elevator opened. As we reached our floor, I held my breath expecting someone to be there, but I was safe and let out a deep thankful sigh. Sierra held my ass cheek as we walked down the hallway; when we got to our room she told me to turn the lights on and open the window curtains all the way up and to open the window as well. I did as I was told, and when I did I was standing facing the main street with nothing but a cock ring on. When I turned around she was taking her dress off and untying her huge cock. There was no hiding her or me from anyone wanting to look. I started a hot shower and cleansed thoroughly. We showered together and she wouldn’t allow me to touch my cock. I was to wash her entire body and that was it.
After we dried off I was told to get on the bed and lay on my back with my towel over my head. I could hear one of our suitcases open and some rustling around when I heard Sierra say “here it is.” She ordered me to pull my knees to my chest, I did and she told me to scoot the edge of the bed and pull my knees back up. I did what I was told and all of a sudden I was being sprayed with lube. She spread it all over my cock, balls and asshole. A moment later I felt her thick spongy cockhead at my hole and in one hard push she buried her cock deep in my ass. I let out a loud “FUCK” and she told me to shut up and take it like a good bitch. She then pulled all the way out of me and shoved her cock right back into me, she did this over and over again until pain became pleasure. With my face still covered she pulled out of me and stayed out.
Not knowing what she was doing, it did finally come to me the events of the day, she wanted me to be her submissive for the weekend. While I lay there with my legs up and my ass exposed I could hear her moving the two chairs in the room, and then her hands on the back of my legs again and her cock stuffed into me and just that fast out of me again. A moment later she told me to turn around and hang my head over the edge of the bed. I spun around and she told me to pull my legs up again. When I did she straddled my head laying her cock and balls on my face, and I could feel her lean over me and push one of my dildos into my ass. She had my double ended dildo; I could feel the divider when it was deep in my ass. She began sliding it in and out of me over and over again making me moan in pleasure.
With her straddling my face I began licking and sucking her balls and ass. I reached around and spread her ass cheeks and buried my tongue into her hole. Both of us were moaning in pleasure. After a few minutes of this she told me to keep fucking myself with the dildo. I did as I was told and she stood back up. When she did she took a step back, she held my feet pulling my legs closer to my chest really opening my ass up. She then told me to open my mouth, and no sooner than she said it she was pushing her cock into my mouth. I had never deep throated a cock her size before but I was about to get a hard lesson. At first she just pushed the head of her cock into my mouth and I sucked it hard and swirled my tongue around it the best I could. She told me to take a deep breath and when I did she began pumping her massive cock in and out of my mouth and then deeper into my throat, gagging me and making me drool everywhere. She slid in and out of my mouth slowly pushing a little deeper each time. I don’t know how long it took but eventually I could feel her balls blocking my nostrils, she held herself there for a moment and then pulled out. I gasped for air right before she shoved her cock back into my throat. I was being throat fucked like never before. Every time she pushed in, she would hold it there for a moment before she pulled out. She did this for a few minutes before she pulled out and turned around and sat on my face again ordering me to eat her ass. She continued to hold my feet as I fucked myself with the dildo.
Sierra stood up and told me to kneel in one of the chairs. When I looked both chairs were facing each other right in front of the window. I did as I was told and kneeled in the left chair. She walked up next to me and shoved the dildo back into my ass. The dildo is a double ended dildo about 18 inches long with a ring divider in the middle giving about 8.5 to 9 inches on each side. She told me to hold it and then she kneeled in the other chair and took the other end of the dildo and slid in it her ass. She shoved back and our ass cheeks were mashing against each other. I reached down between my legs and began stroking her cock as we both slid back and forth on the dildo with our cheeks making slapping noises as we rode it together. After a few moments I remembered that we were in front of the window. I turned my head to look out the window and didn’t see anyone. It was actually turning me on more knowing that someone could see us and hear us moaning and grunting. We rode the dildo for about 5 more minutes when Sierra told me to get on my knees. She pushed her chair back and stood up before shoving her cock in my mouth. She began to throat fuck me again before I felt her cock stiffen up and her cum being pumped down my throat. She held my head as she unloaded in me, she held on so long and hard I was having a hard time breathing, and drool was running down my chin and all over my chest. As I was starting to see black she pulled back allowing me to gasp for air. She fell back into the chair breathing heavily and sweating. I could barely see through the tears but when I looked out the window I could see a young woman across the street watching us, smiling ear to ear. I crawled over to her and laid my head in her lap and she held my head. She told me to take off my cock ring and get in the bed. Again, she wouldn’t let me cum. I was swollen and in pain having to cum. Sierra turned off the lights and got in the shower. She told me to wait in the bed for her and I wasn’t allowed to touch my cock. When she was done she climbed into bed with me and we passed out.
I was awoken abruptly in the middle of the night with her cock entering my ass again. Sierra had rolled on top of me and slid her cock back into me telling me to be a good slut and take her cock whenever she wanted to give it. I glanced at the clock 3:03 am, and I had a 9 inch cock buried in me. Sierra straddled my hips and ground her cock in my ass for about 10 minutes before she filled my ass with another load of cum.
When I woke up around 745am I rolled over and put my arm around her and began to massage her breasts while my cock slid between her cheeks. I wanted to unload a massive load of cum but I wasn’t allowed yet. I ran my hand down her belly expecting to find a sleeping cock but I was sure wrong. She was hard as a rock again, I have no idea how she was recharging that fast, but I was quickly becoming her sub this weekend. I began to stroke her cock and kiss her neck. She reached back and ran her hand over my hip and ass. We laid like this for a few moments when she rolled over facing me. She then rolled on top of me and I wrapped my legs around her waist. She smiled and said good boy! I reached down and placed the tip of her cock at my hole and she pushed into me until her balls were lying on my ass. I was so sore from the night before but I couldn’t say no to her. She hooked her elbows behind my knees and began to piston in and out of me. Both of us were moaning and grunting as she pummeled me. She wore out my ass for over 20 minutes before we even got out of bed. I almost came 3-4 times, but whenever I got close she would slap my balls and tell me no. When she was about to cum, she pushed my legs as far as she could toward my chest and began slamming her cock so deep into my ass I was moaning uncontrollably. When she came she buried her cock so deep into me I thought she was going to hit my spine. She collapsed on top of me and we laid there for a moment.
We both got in the shower and again she made me wash her before I could clean myself. After our shower we got dressed and again she had me wear the cock ring with stretcher and new thong. I wasn’t sure how long this was going to go on but I was enjoying it. She had grabbed her back pack and put both of our bathing suits in it and a towel along with a large sheet we brought to lay on at the Fort during lunch. Her bathing suit was a bikini top and I asked her how she was going to hide her massive cock. She smiled and lifted her dress up and she was already wearing a bathing suit thong made for a man and she said she had a wrap to go over it. As we rode the elevator down to the lobby she began giggling and looked at me and I just told her not this morning, referring to being naked the night before, and she just laughed. As we entered the lobby we saw several people eating Danishes and drinking coffee. I few of them gave us a huge smile and a thumbs up as we left. Sierra and I just smiled and left for breakfast, and I could have sworn I felt her swish her ass a little wider as we left as well.
Day 2 to cum…
Sierra - part 8– Vacation Day 2
As we left the hotel, we could see the old fort down the street so we decided to walk. It was a beautiful morning out and there was a light breeze, so walking was comfortable. Even with this restriction device wrapped around my cock and thong splitting my ass cheeks it was comfortable outside. Feeling more feminine today after last night and wearing a thong, I think I was swishing a little to, lol.
As we approached the fort, she walked me over to a large tree and we kissed for a moment before she reached into her purse and pulled out a small butt plug. She used some Vaseline that she had in her purse to lube it up. She told me stand still while she put it in me as discreetly as possible. My hole was still sore from the night before and she is pulling my thong to the side and forcing a plug into me. Once it was in she put my thong back in place to help hold it in. With her devilish little brown eyes, she just looked up at me and said “anything, I want, remember.” And then she kissed me again.
It was an amazing feeling to just be us and not have to worry about anyone wondering or judging us, if they figured her out. We could just be together and happy. We toured the fort for a while before we decided to go and sit on a bench facing the water and relax. Not thinking, I sat straight down on the plug and it gave me a quick reminder that it was in. Sierra just giggled and teased me a little before kissing me again. We both decided we were hungry after a while and returned to the row of trees on the side of the fort and laid out a sheet we brought with us and our lunch. We ate and then lay in each other’s arms for a little while kissing and caressing each other. Several times I tried to run my hand up her skirt but got smacked instead. After lunch we returned to the hotel to drop of the picnic basket and grab our towels for the beach.
Again, in the elevator, she demanded that I undress and walk to our room completely naked with my cock ring on and my plug in. This time I was actually concerned because of the time of day. But, I did as she asked and undressed. This time I wasn’t so lucky, the housekeeping ladies were in and out of the rooms on our floor. As I walked down the hallway, I heard several ladies gasp and a couple of “oh Shit’s”. Sierra giggled and just said good boy. We got to our room and we put our lunch away and she commanded me to kneel. I did and she immediately put my blindfold back on. She reached down and pulled the plug out of me with no warning, and it shot a bolt of electricity up my spine. Then I heard the door open and close. She commanded me to put my hands behind my back and not move unless told to.
A moment later, I felt a soft cock on my cheek, and naturally opened my mouth to take it in. Immediately, I could tell it wasn’t Sierra, and I began to pull back. Just then I felt a stinging sensation on my ass cheek and Sierra telling me to suck it like a good slut. My brain didn’t know what was happening but I did as I was told. The cock on my face was nowhere near Sierra’s size so it was much easier to deep throat. Whoever was fucking my face began to pick up the pace. I sucked as best I could, when I felt him pull out and slap me few times on the cheek. I was then commanded to lie on my back with my legs up on the edge of the bed. Before I could even get in position I felt hands on the back of my thighs pushing them up as far as he could get them. He spit on my hole and without any warning shoved his 7 inch cock balls deep into my boi pussy. As he began pistoning relentlessly in and out of me, all I could do was whelp in pain and ecstasy. After a few moments, he pushed all the way into me and stopped. Just then I heard him say “Oh Fuck, fuck fuck fuck” and heard a slapping noise from behind him as I felt the impact through him. I knew Sierra couldn’t hold off anymore and was fucking him while he fucked me. Whoever was inside of me didn’t last more than 30 seconds before he filled my pussy up with cum. All I heard him tell Sierra was that he couldn’t take anymore. He whined as I can only assume she pulled out of him. While they were trying to disconnect I peeked out from my blindfold and saw the housekeeping guy pulling up his pants. Quickly, I covered my eyes up again and stayed in the position I was in. I heard the door open and close with no words spoken, and then Sierra walked back over to me and slid her massive cock deep into me. After adjusting to her size again, she pulled my blindfold off and was smiling ear to ear. She continued to fuck me, mercilessly until she filled me with her cum. I knew my role this weekend, I immediately got down on my knees and cleaned her beautiful cock off. She wouldn’t allow me to cum yet or even touch my cock, and OMG were my balls swollen and aching.
We rested for a few minutes and she wanted to swim in the ocean. I went to put my thong back on and she told me to wear a different one. She reached into her luggage and pulled out what looked like a silk thong, but really was poly and it was bright baby blue. I looked at her funny and she smacked my cock and told me to do as I was told. Fuck that hurt, and I put it on. The thong didn’t allow for much room and the cockring/splitter made it impossible to hide what was happening. I was allowed to wear my shorts to the beach but then I had to take them off.
Walking back out of the hotel was questionable, because I had two loads of cum in my ass that were now squishing, leaking and running down my leg. As we walked to the car she reached down behind me and took her finger and scooped up some of the cum and fed it to me. I was kinda freakin out but didn’t want to disappoint her. We drove to the beach and as we got our stuff out of the car she gave me that look. I was being held to my clothing agreement. I pulled my shorts off and tshirt and put them in the trunk. We locked our valuables up and just took her beach bag. As we walked down to the beach it was actually kind of quiet. I was getting stared at from every direction and my cock was responding. We found a spot and laid out our blanket and we quickly got in the water. The ocean temperature was pleasant and the waves were not that bad so we just waded around playing with each other. A couple gay guys came up and said hello to us and Sierra shooed them off. I looked at her and asked why she told them to leave when she just had the housekeeper breed me. She reached down and squeezed my swollen balls and told me not to question her again. I kissed her and said yes. I put my arms around her and under the waves reached down for a grope of that huge cock. She let me stroke it for a little while before she made me stop. She switched positions on me and slid her cock between my cheeks and I begged her not to in the saltwater and sand. She just giggled and said she was teasing me. I spun around and lifted her legs up around my waist and kissed her deeply. We spent the next several hours in the water and lying on the beach. Touching and teasing each other with no other care in the world. We didn’t care how many people saw us, or even saw her massive cock under skirt, we just kept to ourselves. Until about 10 minutes before we were talking about leaving a couple approached us from out of Sierra’s view and said “OMG Sierra no wonder you been hiding!” Now Sierra is very dark skinned and her reaction to the voice I thought she turned pale. They were in their mid-30’s, both white, he was about 6 feet tall and maybe 185 pounds, and she was 5’2-5’4 about 120 pounds and very attractive. Sierra almost leaped up and I could see the both excitement and fear in her face. I stood up, and grabbed her waist to make sure she was ok, and as I did, she reached out and gave them a hug, but kept looking around like she was looking for someone else. She introduced them as Tim and Amy. Both of them were very good looking and friendly. Sierra, introduced me as her boyfriend and obvious play toy for the weekend, which got everyone laughing. Tim, I noticed kept looking at my thong and cock that was pressing out of it, and then would stare at Sierra’s chest. Amy kept smiling at me as well and couldn’t keep her hands off Sierra. I was getting really confused but I went along with it. We made small talk and then they invited us to dinner. We agreed to meet them around 7 for drinks and dinner.
The ride back to the hotel was quiet, and it concerned me. I wanted to go from Sierra’s sub to over protective boyfriend but I knew she would tell me when that was needed. We went right to the room and jumped in the shower together and made small talk about her friends, but she was hiding something, I could tell. I did everything I could to reassure her that whatever was bothering her, that she was safe and I was there for her. She smiled at me and kissed me deeply. Sierra knew how much I loved her spring dresses and she wore the violet one that drove me crazy. I put on some dress shorts and a polo shirt. Right before we left Sierra checked to see what I had on underneath my shorts and I told her my cock ring and a thong. She told me to go commando that I wouldn’t need my thong tonight. Glad I was wearing navy blue shorts. We met them at 7 at the restaurant and we all had some drinks. Tim sat next to me and the two girls sat next to each other. Tim was wearing a similar outfit to me, but much more expensive and Amy was wearing a silk dress that barely covered her. None the less my cock and balls were swollen and hurting even more. The conversation was light at first and then turned very sexual as dinner went on. Throughout dinner, Sierra and Amy were whispering and it appeared to me that Amy was reassuring Sierra about something but I didn’t know what it was. When dinner was over we had another round of drinks and then Tim placed his hand on my thigh and grinned at me. Amy was doing the same to Sierra.
We were in a semi-private part of the restaurant so I let it go. Tim leaned over to me and whispered that my appearance at the beach had both him and Amy so horny and wanted us to join them in their hotel. I glanced at Tim and then Sierra, she smiled at me, and so I looked at Tim and nodded my approval. Tim paid for dinner and we made the short walk to their hotel, which was much more expensive than ours. When we got to the room, Sierra whispered to me that I was to please them and do anything they asked me to do. I looked at her and she gave me an awkward smile, like just do what I ask tonight and I will explain later.
As we entered their hotel room, Tim went right to the bar and poured another round of drinks. I could see that there was a large Jacuzzi in the bathroom and I squeezed Sierra’s hand and nodded to it. She looked at me and smiled and kissed me gently. Then she told me to undress and start the Jacuzzi for everyone. I looked around and Amy was all smiles and Tim was still pouring drinks. I did what I was told and my 7 inch cock was harder than rock and my balls were almost blue from the stretcher. Amy’s eyes lit up and her smile even got bigger. I could see her exchange glances with Sierra and it was like an unspoken agreement between them. Sierra then smacked my ass cheek and told me to do what I was told. I went into the bathroom and not only was there a giant Jacuzzi but a walk in shower. I started the water and got it hot but not burning hot. A moment later, I felt a hand slide over my ass cheek and between my legs squeezing my swollen balls. It was too soft to be Sierra so it had to be Amy. When I turned around she was running her hands all over my chest and stomach, like I was some kind of statue. Amy looked up at me and told me to undress her.
I gently took my fingers and brushed her hair back off her neck and found the silk string that was holding her dress up. Now I am 6’3 and about 220ish and solid muscle back then, so I towered over her. I grabbed both of her shoulders and spun her around in a controlled but seductive way. As I did this I heard her whimper and take a deep breath. (Mind you I haven’t been with a true female in 6-8 weeks) I pulled her to me so that she could feel my body against hers, as well as my cock in its glory pressing on her lower back. I hooked my thumbs in her hair and gently pulled it back and to the side. I gently kissed her shoulder and when I did she reached back and grabbed my thighs for support. I reached up and gently pulled on the loose knot that held her dress on. Our bodies caught her dress between us and only exposed her B cup breasts. Her nipples were pink and only a few shades darker than her milky white skin. I ran my hands over her stomach and up to her breast cupping them fully with my hands. She whimpered again and reached up to put her hands on my head as I kissed her neck. I glanced up to see if Sierra was watching but she wasn’t. Amy pulled away from me and her dress fell to the ground exposing her small clean shaven pussy. She took my face in her little soft hands and said don’t worry that Tim was pleasing Sierra for a few minutes. Just then I could hear the tell-tale gurgling of Sierra’s massive cock in Tim’s throat. We both smiled, and Amy told me that I was told to do anything she asked. I nodded and said yes. Amy then told me get the soap in the Jacuzzi and start the bubbles. I did as I was told, and as I bent over Amy playfully slapped my ass cheek. I was then commanded to bath her from head to toe.
As I was doing what I was told, Sierra and Tim entered the bathroom completely naked. Now Sierra makes my heart jump whenever I see her naked but it was the first time seeing Tim naked. He had a runners body, fit but not overly muscular. Clean shaven from the face down. His cock was wonderful to look at, 7.5 inches and as thick as a redbull can. His balls weren’t very big but still nice. His ass was thin but still nice to look at.
I was kneeling in the Jacuzzi washing Amy when they both decided to get in the walk in shower. Sierra had a way of making men do what she wanted them to do , because she spoke to Tim like she had been speaking to me all weekend, like a sub. Tim got the water to the right temperature and then began to wash Sierra from head to toe. If he tried anything other than washing her, she would smack him and make him apologize. I continued to wash Amy and give her all of my attention. Amy told me to lift her to the edge of the Jacuzzi and to make her cum. I kissed my way up her legs, gliding my hands up and down as I went. Watching her bite her lip in pleasure. As I kissed her thighs she moaned and held my head and began pulling me to her pretty little pussy. I spread her legs as far as I could on the edge of the Jacuzzi and her pussy was swollen and red and begging for release. I kissed the soft puffy area right above her clit and I could smell her juices already. I ran my tongue gently downward and I thought she was going to fall off the edge of the Jacuzzi; I wrapped my arms around her thighs and held on to her. My first touch to her clit caused her to buck up into my face over and over forcing my tongue into her tiny slit. Her juices were covering my face now and she begged me to make her cum. So I latched onto her clit and sucked on it while my tongue swirled rapidly around her clit. This only took about 30 seconds and it took everything I had to hold onto her while she orgasmed. I sucked and licked until she begged me to stop. She flopped like a ragdoll back into the water and grabbed my head and pulled me in for an amazing deep kiss. Just then I could hear Tim still choking on Sierra’s cock. I sat down next to Amy and pulled her into my arms while we watched Sierra dominate Tim.
As Amy laid in my arms in the jacuzzi, I ran my fingertips up and down her belly and around her very erect little pink nipples. My cock and balls hurt from being restricted all day, and now pressed in Amy’s lower back, I wasn’t sure how long I could hold out from fucking her brains out.
Sierra was throat fucking Tim in the shower and we could see the tears and drool pouring down his face. He was taking about 3/4’s of her massive cock. She would push it in and hold it for 10-15 seconds and then pull out making him gasp for air. Amy just stared in amazement. I ran my fingers back down to her tiny little pussy and started making circles around her little clit, and sliding my fingers into her tight pussy. Her back arched and she was gripping my thighs tightly, until she spun around and kissed me deeply like she was starving. In between breaths she told me to put my cock in her. I did as I was commanded; I lifted her small frame up and slid her forward onto my raging hard cock. The soft velvet feeling of her pussy almost put me over the edge, but I managed to hold her down and not let her move for a moment until the urge to cum subsided. Once I regained control she began rocking her hips back and forth grinding on my cock. It felt amazing, seeing that I hadn’t any pussy in about 2 months.
While Amy rode my cock, I looked over her shoulder and Sierra had Tim face down in the shower about to push all 9 inches into his tight little ass. I stopped Amy and told her to watch. She whispered to me that this would be the first time she had fucked him. It was usually the other way around. When she said that I immediately knew why Sierra had been acting strange all afternoon. Amy watched Tim take Sierra inch by massive inch into that tight little ass. While Amy was mesmerized with what was happening with Tim, I turned her around and placed my cock back into her from behind and let her grind on it while her husband took my girlfriends massive ebony cock. Tim was moaning uncontrollably, but that only excited Sierra, after a few minutes she was balls deep in him and he was mumbling incoherently. Amy was watching so intently that it was like her orgasm snuck up on her and she was in shock as her body trembled.
I couldn’t take it anymore, I needed to serious fuck this beautiful woman the right way. I told Amy to stand up, and she did, I stepped out of the jacuzzi and picked her up and set her down on the bathroom sink counter and pushed her legs up and told her to hold them. I reached under me and pulled the splitter off my balls, I was going to fill her pussy full of a days’ worth of built up cum. I didn’t hesitate, I pushed into her pussy in one smooth motion, and Amy let out an “Oh Fuck” as I buried my cock fully in her. I knew I wasn’t going to last too long so I began pistoning in and out of her as hard as I could. All she could say over and over was “Oh Fuck, fuck, fuck” and all I could do was grunt like an animal. I fucked her as hard as I could for a few minutes before I felt my orgasm building. I hooked the back of her knees on my elbows and lifted her off the counter and bounced her off my cock until I couldn’t take it anymore and buried my cock as far as I could get it in her pussy and flooded it with cum. I came so hard I began to get dizzy and set her back on the counter. Both of us were trying to catch our breath, my cock still inside of her, gently moving back and forth. She pushed on my belly to get me to stop, As I pulled out of her my cum was leaking from her and she looked at me and told me to clean my mess up. I did as I was commanded, and kneeled before her. My tongue dove straight in and began lapping up all her juices and my cum. As I did I would gently flick her clit from time to time until she grabbed my head and pulled me back onto her clit, I swirled my tongue around her clit for a few seconds and I felt her body tighten up and start to spasm for the 3rd time. When she did more of her and my juices flowed out of her tight little pussy and I finished cleaning her up as I was told.
Amy and I came out of our little intense session and heard Tim still getting plowed by Sierra. Sierra was fucking him like she was possessed tonight. Sierra looked at me and smiled, and pulled her cock out of Tim and told him to stand up facing the glass. She pushed his face into the glass and slightly pulled his hips back and sank all 9 inches straight back into his ass. I knew what was about to happen, and as I was kneeling between Amy’s legs, I told her to watch his cock. Sierra began to thrust deeply into Tim and I could see his eyes roll back and I knew she was rubbing on his prostate. Moments later Tim began to shake uncontrollably and cum began pouring out of his cock. Amy gasped and asked what was happening, why was he cumming without touching his cock. I told her that Sierra’s cock was rubbing his prostate and he was having an orgasm like a girl. Amy was amazed at this. Sierra didn’t let up either, Tim begged her to stop but she wouldn’t, Tim began pouring more fluids from his cock and almost lost his balance. Sierra reached around and pinched his nipple with one hand and pulled his hair with the other arching Tim’s back before she pushed all the way into him and unloaded a massive load deep into Tim’s ass. All Amy could say was that it was amazing to watch and made her so much hornier. Sierra slowly slid her cock in and out of Tim for another minute before it plopped out. She grabbed Tim by the hair and told him to kneel and clean her off. Sierra took a step back and Tim leaned forward to suck and lick her clean. When he did, we had a perfect view of his gaped asshole and the cum pouring out of it. Amy gasped under breath and began to rub my chest again and stroking my cock. Amy commanded me to put the spreader back on my balls and to fuck her again. In my mind I was cussing but I couldn’t let Sierra see me hesitate, so I did as I was told. Amy stroked my cock until it was hard and I spun her around facing the mirror and slid in her tight little pussy in one smooth motion. I grabbed a hand full of hair in one hand and her hip with the other and began long stroking her velvety pussy. Slow but forceful were my strokes making her mouth open but she couldn’t say anything. As I am fucking her from behind, Sierra walks up behind me and wraps her arms around me as I long stroke Amy. Every time I pulled out of Amy I could feel Sierra’s limp cock rub my ass cheek. Sierra just stood there holding me from behind, and then started rubbing my pecs and pinching my nipples.
The arch I had in Amy’s back gave me deep penetration and she felt incredible. Sierra whispered in my ear that I was not to cum before Amy, which was ok with me. I had already came once and had whiskey dick.
I continued fucking Amy as hard as I could, hearing her “Oh Fucks” and her whelps made me even harder. Mid stroke Sierra, whispers in my ear to fuck her ass. I smiled at her and took some of Amy’s pussy juices and smeared it on her tiny little rosebud. Amy quickly turned to me and had a look of panic in her eyes. Sierra looked at her and told her to take my cock and to enjoy, that she was the only one not to get fucked in the ass tonight. Sierra slapped me on the ass and said what are you waiting for.
I pulled my cock out of Amy’s amazing pussy and pressed the head of my cock on her little rosebud. Amy pleaded with me to be gentle. Sierra then grabbed my cock and Amy’s hip and pulled us together, shoving my cock about half way in. Amy cried out and I just held still. I looked over my shoulder and Tim was kneeling about 10 feet away not moving. I assumed that Sierra had told him not to move and to just watch.
When Amy caught her breath I went balls deep in one push. Amy cried out again and Sierra stepped out from behind me and spanked her ass cheek hard leaving a red hand print. Sierra nodded at me, and I started sliding in and out of this super tight, hot, soft hole, at a moderate pace at first. Sierra kissed me and then gave me a devilish grin, and told me to fuck her harder. Her ass was amazing, tight and hot and became very juicy. As I increased my pace, Amy increased her cries and moans. Then Sierra pulled her hair up into a pony tail and held it there. Amy looked at Sierra with water in her eyes and Sierra just reached down and grabbed her limp cock and put it in Amy’s mouth and told her to suck. I looked back at Tim and I could tell that he wanted to stop us from spit roasting his wife but knew better. I continued pummeling her as Sierra tried to shove her huge cock in Amy’s little mouth. Amy could only get the head of her cock in her mouth and I could see Amy doing the best she could to suck and swirl her tongue around Sierra’s large spongy head. After a few minutes like this Amy was no longer crying but moaning in pleasure. At some point Amy was losing the ability to stand up, so I wrapped my arm around her waist and held her. I continued my fast pace but I could feel a climax was coming soon. I reached under Amy and began to rub circles around her clit and finger her pussy. That didn’t take long for her to have a quivering orgasm and lose her ability to stand, she was like wet spaghetti. Sierra pulled her cock out of Amy’s mouth and smiled at me, giving me permission to cum in her ass. I held Amy with one arm under her waist and the other I grabbed her small breast and held her up and fucked her ass as hard as I could for what seemed like 10 minutes but realistically it was probably 2-3 minutes before I shoved my cock as far as it would go in Amy’s tight little ass and unleashed my load deep inside of her.
Sierra had Tim by the hair dragging him over to his wife ordering him to clean up her ass from the breeding she just received. Amy had collapsed on the floor face down and Tim got between her legs and began licking and sucking my cum out of her. Sierra ordered me to get dressed. I was spent and it took me a minute respond and she slapped my thigh and told me to hurry up. I got up and dressed and waited by the door. A few moments later all three were coming to the door and Sierra had her violet dress back on. Tim and Amy were still naked and visibly shaking from exhaustion. Amy and Sierra hugged each other and I heard Amy whisper to Sierra that she wouldn’t tell. I knew what was going on now but didn’t say anything.
Sierra and I walked back to our car and returned to our hotel. As we got in the elevator I looked at Sierra and she giggled at me and said not tonight. I sighed in relief and kissed her. We got back to the room and I started a hot shower. We both got in and I washed us both in silence. I was gentle with Sierra and held her reassuringly for a while. We got out and I dried us off and we laid in the bed with the tv on until we fell asleep.
Sunday morning we got up and ready for the day. I asked Sierra if she had anymore requests of me. She walked over to me and pushed me into the chair and straddled me, wrapping her arms around my shoulders and neck. She said no more requests for my sub boy and giggled. She said that she always wanted to be the boss and thanked me for trusting her and following her commands. She said she was testing my trust and I had passed. I looked at her and said “on the topic of trust, Tim and Amy?”, “I figured out the link.” Sierra’s eyes began to water and I told her to stop crying. She sniffled a few time and told me that she had been “given” to them before by her ex-boyfriend. I looked at her and said “Given?” She said yes, that she was forced to be with them the first time, but after a while they actually became friends. I listened to her tell me the story and instinctively turned into the protective boyfriend. I said if they tell him that they saw you, then what happens. Sierra just started tearing again and told me that she couldn’t be found again by him.
I asked her if last night was her way of trying to keep them from telling him and she nodded yes. I looked at her and playfully said at least it was fucking hot sex. She giggled through her tears and smacked my chest. I wiped her tears and kissed and gave her a strong hug. She kissed me again and said that I was back in charge. I sarcastically said “oh thanks” and we both chuckled. We sat there for a moment just looking at each other and out of nowhere she tells me that she thinks that she is falling in love with me, and then looks down away from my face.
I lifter chin back up and kissed her passionately, I wasn’t ready to repeat those words but I was definitely feeling that I could be one day. I glanced at the clock and noticed it was check out time. I picked Sierra up as I stood up and carried her to the door, she just held my neck tight not wanting to let go. I put her down and grabbed our bags and we turned our keys in and packed the car up to leave.
A few hours later we were back at my apartment. The car ride was just idol talk, I didn’t want to get into the possibility of Tim telling her ex that they saw each other just yet. Sierra decided to stay at my apartment Sunday night, so we spent the day doing laundry and grocery shopping for the week. We used the apartment grills to cook dinner and have a drink before going to bed. I had to work in the morning and both of us were exhausted.
Throughout the night I could feel Sierra tossing and turning so I rolled over and wrapped my around her and pulled her close to me. A moment later I could feel her crying and I rolled her over and pulled her into my chest. She just whispered that she was scared of him finding her and losing me. I pulled her closer and told her that there was no chance of that, and she cried herself to sleep. A few hours later my alarm went off and I gently rolled out from under her and I jumped in the shower. She didn’t budge, even as I cooked breakfast and made coffee, she didn’t move.
A few hours later I got a call at work from her telling me she was going to her apartment to do some things and she would talk to me before bed. I was worried about her but she needed the space to think and figure out the next move so I didn’t bother her. She knew I was a phone call away if she needed me. Later that night she called me to say goodnight and we chatted for a few minutes and we hung up. About 2am I hear knocking on my apartment door so I jump out of bed and without looking I opened it with a grumpy look on my face and immediately changed my look when I saw it was her. She smiled and I could tell that she had been crying again. She came in and said she didn’t want to be alone, so we crawled in bed and held each other until we both passed out. Unlike yesterday, she was up first and cooking my breakfast while I was in the shower. When I got out of the shower she came in the room only dressed in one of my t-shirts. Her cock swinging away under it making me start to get hard. She gave me this devilish little grin that I have seen before, and she pushed me against the wall and kneeled in front of me, my cock instantly responded and she sucked me like she was starving. She played with my balls and ass as she throat fucked herself. At this pace it wasn’t going to take long for me to blow. I grabbed her head and began to thrust forward each time she went down. I would hold her there for a few seconds and then would pull out, and each time she would gasp for air and I would push my cock as far as I could back into her throat. After about 5 minutes I could feel the pressure building and I told her. She sucked even harder and when I started to tighten up, and in a few more strokes I was unleashing 6 thick streams of cum down her throat. She took every drop and kept sucking me and cleaning my cock off as I went limp. When she was done she stood up and kissed me and thanked me, I looked at her and said thank me, I need to thank you and we both laughed. Nothing was said about the night before and I went to work.