My Trip to Boston Ch. 01
On Friday, me and E didn't leave New York until close to 1pm to get to Boston, which was bad timing on our part. A normally four hour trip ended up taking nearly seven hours. Still, it wasn't a terrible ride. I was incredibly horny all day because I was really looking forward to having sex in the hotel. E did most of the driving and while he did, I spread my legs on the dashboard and played with myself in full view of passers by. E didn't mind my exhibiting and that got me even more aroused. We hit some traffic and stopped twice, so we didn't get to the hotel until close to 8. The hotel was beautiful, upscale and in the center of town. It was also attached to a fancy shopping center called 'Copley Square'.
We had a reservation that night for an elegant restaurant near the hotel, but I wanted to change and wash up first. I did that quicky in our room and we got to the restaurant around 9. That was an amazing meal. I ordered seafood stew and we each had 2 glasses of Pinot Grigio. E had seared tuna steak. I enjoyed the food, atmosphere and service. When I went to the rest room, I took off my panties and handed them to my husband as I sat back down at the table. He was amused and he put them in his pocket.
Then, we had an interesting follow up conversation that would define how the rest of the weekend would play out. Earlier that week, E told me, at home, that he would help me live out my fantasies to have sex with other men, women or maybe couples. When I reproached him on the topic at dinner, he revealed that he was not truthful when he said he'd go along with that. He then admitted, it was 'just pillow talk' on his part in order to arouse me. He said he could never go through with it, because he was only comfortable with me, alone. I was disappointed to hear that, but I knew I couldn't force him into my fantasies. I told him, "That's fine, but I am going to do what I am going to do."
When we were finished with dinner around 11, we walked back through Copley Square to the hotel and hubby told me he was tired. He wanted to go to sleep but I wanted to go to the bar! I wanted to enjoy the feeling of eyes and possibly, hands on my body. I was all dressed up, wearing a short, yellow, silk dress with nude, patent leather stilettos. My makeup was impeccable and my hair was blown out.
I did not look around much going into the bar but I sat down next to some empty seats and ordered a glass of wine and some ice water. About 10 minutes later, this guy came and sat next to me on my left. I immediately thought he was very suave and sexy. From what I could tell, he had a nice body. He had dark hair, but not a lot of body hair from what I saw, in his rolled up sleeves of a button down shirt.
He had a fresh plate of food and a glass of wine brought over. He offered me some food and started a conversation. He was very friendly, charismatic and good looking and I concluded in less than 20 minutes that we'd be fucking. I wanted to fuck him then, but I gave our conversation an additional 40 minutes to make sure no red flags went off. During that time, the conversation turned sexual, which I may have instigated. He told me about some of his adventures and I mentioned some of my preferences. I told him that I like to submit and that I enjoy anal sex. This led to some story swapping and he showed me some pictures of one of his fuck buddy girls.
He was cocky but flat out told me that he was unattached, at the hotel for work and loved anonymous sex. That was something I could definitely go along with. Around midnight, he offered me the invitation to go to his room with him. I accepted.
I was very aroused, as I had been all day. My panties were already off and my pussy was swollen and wet. We got to his room and we walked in. I noticed he had two beds and only one appeared to have been slept in. I sat on the bed that was made. He said: "Oh, my secretary booked this room for me, I think it was a mistake, that's why there are two beds." I thought "Who uses the title 'secretary' anymore? Aren't they called 'assistants' these days?... Whatever." He claimed to be an Art Programmer from New Orleans but added he used to be in the Military. I honestly thought he booked a room with two beds so he could have one bed to sleep in and one bed to fuck in. Based on our talking, he clearly enjoyed many casual encounters.
What I could genuinely say, is that he had a very nice body. I could see his built biceps through his shirt. I commented on his size and we built up even more sexual energy by talking about our physical attributes. He conceded to being 6'4 and 245, after he noticed my 5 inch high heels and I admitted to being only 5'1. He said that he especially likes petite blondes but got even more excited when I also mentioned that I'm very flexible.
I took off my shoes and went into his bathroom to wash up and take off my dress. I came out in just a black, lace bra, yellow gold bracelet and earrings. He already had his pants and shirt off, but I liked the sight of him in just his blue boxer briefs. He had some enigmatic tattoos but I didn't ask about them for fear of wasting valuable time. Maybe, I didn't care much, either. I was right about him not being very hairy though. I could see that he was very hard for me and his dick was huge! I don't know how many inches but it was, at least four fingers wide and seven or eight long if I had to estimate. He enjoyed talking about how big his cock was and how he used to think it was small compared to his older brother when he was a kid. Even if that was the case, he was very proud of his unit now and I anticipated enjoying it fully.
As he was taking off his shorts to show me his naked body, I sat down on the bed and then he removed my bra and dove right into my pussy. My clit was already hard and sensitive and his mouth's strength matched the rest of his body's fortitude. He stuck a finger in my tight slit while sucking and licking hard for dear life. And then, he stuck a finger in my ass, which I loved! I could have told him to do it softer but it was making me cum and I didn't care if I came all over his (fuck) bed or face. I could feel my hips bucking and I may have squirted but he was still going.
Finally I called out, "let me suck your cock" because I wanted to pleasure him back and, I was nearly overstimulated. He was more than happy to oblige. He laid down and guided my head down to his crotch as I crawled between his legs. I opened my mouth wide as I was on my knees and I caressed his balls and stroked his shaft. I took him a little further into my throat with each suck. He ordered me to lick his balls, which I did, and used it as a break for air. But, I also enjoyed being down there because he was shaved so smooth!
Since my face and hands were on his pelvic region anyway, and he'd been playing with my ass, I felt compelled to do the same to him. I'd never done that to a guy before, but I looked up at him as I touched his bud with my finger and he didn't stop me. He looked like he was enjoying it and pleased that I did it on my own account. I slowly but firmly probed his ass with the tip of my middle finger while I sucked his balls and stroked his shaft. It was really enjoyable looking up at him and seeing his eyes stare back at mine with a sensational look on his face.
The eager gaze on his face started to become very intense. I could tell it was time to change positions, or he might have cum at that very moment. I felt ready to take his cock inside of me, so I pulled myself even closer to him. Having picked up on my cue, he asked, "Do you want me to fuck you now?" And I replied "Oh yes!".
He sat up, pulled open the side table drawer and right next to the Holy Bible was a pack of rubbers and a bottle of lube, and I thought '...dude came prepared, he obviously does this a lot!' My pussy was dripping wet at this point so no lube was needed, yet. He then turned me over on my stomach, pulled my legs together and entered my pussy from behind. It was a little painful at first, until my tight cunt accommodated him. He was very careful not to injure me, which I really appreciated. In fact, he was very aware of his size, but also attentive to every moan, whimper or gasp that came out of my mouth.
All while he was filling my pussy with himself, he grabbed my arms and held them together, behind me. I could have freed myself easily but it felt so good just to be held down and pleasured! And then, with his free hand, he once again prodded my asshole with his finger. It just made me moan and writhe even harder under his grasp. I felt myself leaking cum and my feet swung up and hit his ass behind him as I made his bed moist with my juices. He reached around my face and stuck his fingers in my mouth to suck and then leaned forward and turned my face towards his. He kissed me while he put in a few more thrusts of his hard-on into my slit.
He let my arms free, and then he picked up my hips and started fucking me doggy style. I looked up at him over my shoulder and he smiled as he smacked my ass firmly but not hard enough to leave a mark. I was moaning, smiling and grabbing the corners of the bed sheets around me to secure my grip. Having him finger my ass while he screwed my pussy so good made me beg him to please, please 'fuck my ass'. Then, I remembered, the guy was huge and as soon as I processed the words that came out of my mouth, I felt him get up, open the drawer and gave me a sensation of cool lube mixing with my juices, all in my bottom. He fingered my ass again, with more lube, and started to enter me there. He got a quarter of the way in, but it was painful. I uttered "Not yet, I'm still too tight" as I winced. He immediately pulled out.
It had been years since I've had a good ass fucking, and I was never very experienced to begin with, except for playing with my own toys in my own capacity. But luckily, he knew what he was doing and he was really good at it!
"Don't worry." He said, and made sure I still wanted it. Not giving up, he then stuck two fingers in my ass with more lube and loosened me up for a good few minutes while I laid there, again stomach down. The massage was heavenly. And to add, I reached my own hand down, underneath myself, and massaged my own clit while he managed to relax my less explored tunnel.
He sat back up against the head board and told me "Go in reverse cowgirl.". I got on top of him and faced out on my back. Finally, he could tell when I was relaxed enough, and he slowly, but firmly entered my asshole with his large cock. He fucked my ass slow to start. I easily reached down to rub myself as I watched everything in the mirror opposite the bed and I ordered him to pull my long hair, which he did very compliantly. I loved watching us fuck in the mirror and even though there was such a big height difference, it didn't feel awkward at all. It felt amazing. He let go of my hair and I discovered that having all of him in my ass with my clit being rubbed while I fingered myself was enough to send me over the edge. I came again.
It was sometime after 1am and we were about to change positions again but we fell into a tangle when I heard my cell phone ring. I got up to answer it. It was hubby, wondering where I was. I told him "I'm at the bar." But, I wasn't sure if he believed me! He continued, in a sleepy voice "Where are you? You're still at the bar? When are you coming up?" I did my best to pacify him but he sounded suspicious.
When I finally ended the call, we got right back to work on our incredible fuck session. He laid me on my back, on the side of the bed, facing the side table and he folded up my legs, Indian style while he re-entered and pounded my pussy some more. He seemed to really enjoy putting my legs in different positions, and the fact that I was so pliable. It didn't hurt that he also had a ton of upper body strength. And, those blue eyes of his, they seemed like intense slivers of light sky as I looked up at his tall frame as he was standing up against me.
I glanced at the clock on the night stand and processed it was close to 1:30 am. I had cum a bunch of times, so I was satisfied. I told him "I want you to cum for me." He stayed standing by the side of the bed as I sat up and leaned my body toward his pelvis. He took off the condom and put my mouth to his balls while he stroked his cock. I once again, penetrated his tight hole and fucked him with my finger but went further up and vibrated my wrist against him. He jerked off while I sucked his balls and when he was ready, a minute after, he stuck the head of his cock in my mouth, which I opened wide for him as he came. I wanted him to see how much I enjoyed myself. Then, I immediately got up and re-dressed so I could get back to hubby.
He was talking to me as I was leaving but I didn't really take in anything he said. I did however enjoy his kiss, which felt like a hug in my mouth. It was very firm and nice and I told him he tasted like wine and pussy. His dick was still hard for me when I left the room.
Finally, about five minutes later, I got back to my room and hubby was like: "So where were you?... Are you sure you were at the bar..."
And after all the questioning, I plainly said: "Okay, you got me, I went back to some guy's room and had sex all night... I don't even know his name... he fucked me in the ass...."And he reacted by saying: "That's it. I'm going to sleep. When we get back, we're getting a divorce... and I'm like "okay, that's fine. You can do whatever you want and I will do what I want." I got undressed and washed for bed but I realized I lost an earring. I figured it was probably left in my preceding beau's room. I reckoned it was gone for good.
I finally got into the king sized bed and then E said to me: "Did you really do all that or were you really at the bar?"
and I answered, "I was at the bar."
And he remarked: "Oh, good one! I really thought you might have gone up to someone's room." I was too tired to continue any conversation at that point but then E rolled towards me and started to grope me, like he does when he wants to have sex. It was a good thing it was so dark in the room, so he couldn't see me roll my eyes.
All I could think was "My pussy is going to be so sore!" And, it was 2 am, no less. But, despite the fighting and fatigue, I was still worked up and horny. So, I made a decision to put out for peace. I sucked his dick a little, I rode on top of him for a few minutes, and let him cum in my pussy like a good (slutty) wife. He was tired too but it was still nice.
I ended up staying awake most of the night. I was very wound up! I couldn't help wonder if I'd run into my cavalier flame again the next night. I was also a little upset about losing my earring.