Fun and Games Ch. 07

Tim had to go out of town for a week, so my body began to take a much-needed break from anal sex.

As I adjusted to the lack of a penis stretching me on a daily basis, I realized the respite was somewhat welcome and somewhat not. In a short span of time I had become virtually addicted to sucking cock and getting ass-fucked, and after five days without either I was edgy. I emailed Tim a few times while he was out of town and masturbated at least twice a day, and whether I wanted to admit it or not I was anxious for his return. It had become normal, as normal as such a thing is, for us to hook up and it was clear from our communications that we were ready for another round of fun as soon as he returned.

Thankfully the weekend was quickly approaching. On Thursday, the day before Tim returned home, he emailed me and said that I should keep the weekend open, and that Friday would be a good night to "get dressed up and make your fantasy come true" which I assumed was a euphemism for fulfilling my longstanding fantasy of dressing up in pantyhose and getting used in a dirty alley. He suggested we meet at a place called Telly's, which was downtown near the club where we first met at the concert. From the outside Telly's looked like a decent bar but I had never gone in.

After I got home from work on Friday I decided to get naked and slide on my pantyhose and stand in front of a mirror. I was going to dress up to deliberately look somewhat effeminate to match my silky hose under my clothing to set off my fantasy. I was so excited I could barely contain myself. The mere thought of it made my cock strain against my tight silky hose.

The drug store down the street provided the mascara, which I decided was as far as I would go this time.

Wearing my pantyhose, a t-shirt and jeans, a closed-toe pair of sandals, and a touch of eye liner I was ready to hit the bar. Tim said he would be there around 9:30, which was well after dark. Deliberately trying to look effeminate put me squarely outside my comfort zone, but I pressed on and walked into the bar, figuring that Tim would appreciate and reward my actions.

I beat Tim to the bar, so I sat down and ordered a drink. A hockey game was on so I got involved in watching it and shot the breeze with a few patrons and the bartender. After about 15 minutes I began to notice that no women were walking into the bar, although in many 'shot and a beer joints' that was ordinary so I didn't think much of it.

I was about to order another drink as the bartender tossed a chip down in front of me for a free drink. I thanked him and he said, "Thank him" and pointed to a man at the end of the bar. The guy waved and I waved back.

As the bartender brought my drink over the guy from the end of the bar came over and sat down next to me. This was obviously of Tim's doing, I thought, so I played along.

"Hey, how you doing?", I said, shaking his hand. "I'm Jake."

"Nice to meet you Jake. I'm Aristotle. Enjoying the game?"

"Yeah. I'm a Rangers fan so I'm not emotionally invested in this one."

"You get emotionally invested in hockey games?" he laughed.

"Definitely!"

"What brings you downtown tonight?"

"I'm here to meet a friend of mine. How about you?"

"Me? I guess you could call me a regular."

As Aristotle and I conversed, I was thinking that Tim should have made his friend a little more subtle. This guy was practically leaning on me. I didn't find him particularly attractive, but then again I didn't think Tim was attractive either. He was about 40, about five ten, sort of slender, almost skinny. He appeared to be of European or Greek descent, with dark skin and eyes and a charming accent.

"You have a bit of an accent", I said. "Where's home?"

"Ah!", he laughed. "After all these years my native tongue betrays me. I'm from Greece. I have lived in the United States for over 30 years. In fact, I live upstairs."

After a few seconds it hit me. Telly's. Aristotle.

"Is this your place?"

"Yes, it is. I hope you like it. I bought it about 12 years ago and I've worked hard to make it a pleasant place for all kinds of people to gather. It makes me happy to make others happy, and what happier times than sharing a good meal and a drink, eh?"

"Absolutely. That's a long time to own a bar."

"It's actually more of a restaurant than a bar", he said with a hint of understandable annoyance in his voice. We do more business during the day than at night. At lunch time we take reservations every day believe it or not! I am very proud of my cooks, my sister and my brother."

"I'll have to come over for lunch some time. I only work a few miles away from here."

"Well, you are ready for another drink and tonight is my night off, so will you have another drink with me, friend?"

"Sure thing. What are we having, Ouzo?"

"Oh, I hate that stuff", he said, laughing. "Rum drinks for us."

The bartender made us a few drinks and we talked some more about a variety of subjects, even testing the most forbidden of all topics...politics. As it happens we shared some views and politely differed on a few. Time flew and the drinks were flowing and before I realized it I wasn't missing Tim at all. It was 11:45 and he was a no-show, no texts, no calls. But I was having such a good time talking to Telly that I was content and somewhat glad Tim wasn't around at the moment.

By 12:15 I was heavily buzzed and ready to start sobering up so I could drive home.

"I'm going to take off, Telly. I need to get something to eat before I drive home and your kitchen is closed, so..."

"Well, can I make you something to eat? You can join me in the special area of the kitchen as my guest. It is nothing, really, just a small table where my family sits and eats when the restaurant is full. Join me, won't you?"

I accepted and we went into the kitchen which was through a hallway and through a set of swinging doors. Telly turned on the lights and began to rummage around in the refrigerator.

"Hey, I don't mean to put you through any trouble", I said.

"Oh, please, what trouble? You are hungry and I am an excellent cook, so what trouble is there in this?"

In a matter of minutes he had a pan frying lamb and vegetables, and had pulled out some spanikopita for us to snack on.

"Wow, this is fantastic!", I exclaimed. "I was ready to go to Burger King!"

"Ah, nothing. You should come for lunch some time or dinner on weekday nights. Then you would have a very good meal."

Obviously fishing, Telly said, "You should bring your girlfriend. I would give you my best table."

"I would if I had one. No girl at the moment." It occurred to me, finally, that in a brightly lit kitchen my eye liner would be much more obvious than it was in the bar; my stomach sank in embarrassment.

"Ah, some handsome man like you, no girl? What a shame."

"What about you Telly? You have a girl right now? Are you married?"

"I was married many years ago. She was a wonderful woman and I lost her to cancer. She was beautiful, and delightful, and so smart. I miss her even today. There is her picture." He pointed to a lithograph of an oil painting, the subject a stunning Greek woman.

"Telly she is gorgeous. I'm so sorry."

"Losing my Andrea changed me so much", he said. "I now have girlfriends and boyfriends and I don't even know what any more", he laughed nervously. "I hope you don't judge me for that. It was so devastating."

"No, why would I judge you Telly? You deserve to be happy."

"Yes, sometimes I am happy. I am happy now talking to you."

The silence was a little uncomfortable, and I broke it by suggesting that I should get home.

"You had a good bit to drink. Maybe you should wait a little while before you drive. I do not want to be responsible for my new friend to get hurt. You are welcome to talk with me for a while, or maybe you could join me upstairs. I am only suggesting..."

Before I could open my mouth to say goodbye, I heard the words, "Sure. Let's go upstairs" roll off my tongue. I could hardly believe it, wishing momentarily I could reel them back, but seeing the happy look on Telly's face, I was suddenly up for an adventure. I took another quick glance at my phone and still no messages from Tim.

There was a back staircase from the kitchen to the upstairs apartment. My heart was racing and my mouth was dry as I took each step which sent shock waves through me as I inched toward this strange man's apartment.

Once inside there was little reason for either of us to hide why he invited me and I welcomed his advances.

He moved toward me and put his hand on my crotch and I practically jumped. I was so nervous I was breathing through my mouth and felt instantly sober.

"You like this?", he whispered.

"Yes", I managed in a husky, hushed voice.

"Would you sit down for me?", he asked.

He moved me toward his bedroom and sat me on the edge of the bed. He unzipped my jeans and pulled them down, revealing my erect penis held in place with my sheer pantyhose. He breathed loudly and moved his mouth toward my penis, breathing hot and hard on it.

"So nice and silky", he whispered. "How nice. Do you wear these often?"

"I like to once in a while. It's something different. Sort of a fun thing to do."

"Yes, I like it. Makes you look very sexy in them. I like how it holds your cock in place", he muttered.

He worked my jeans off leaving me wearing my pantyhose and a t-shirt, with my cock straining against the front. Telly reached inside the waist band and slipped my cock through the front hole and it sprang free. He slipped it into his mouth quickly and easily. He knelt down and began to slide his mouth down my hard cock while he felt my legs. Not to be critical, but he left much to be desired in the cocksucking department. Tim and Ron were hard acts to follow, but he was trying his best so I encouraged him. I slipped my cock out of his mouth a few times because he was dragging his teeth on my penis, which I did not like at all. I moved his hands to encourage him to massage my balls through my pantyhose, and as he began to suck a little softer I became very excited. After a few minutes of this new technique I was getting close to orgasm.

"I'm going to come", I said.

He quickly pulled his mouth off and squeezed the base of my cock to stave off my orgasm. "I have protection...if you want to."

I nodded and he disappeared and returned naked with condoms and lube. His cock was much smaller than Tim's or Ron's, and I sort of breathed a sigh of relief! It would be no problem to take my new buddy's dick up my ass, which I thought would be fun.

"You can go first if you want to", I said.

"Oh, yes, that would be good. I would love to", he said.

We moved around and decided to lie down on our left side and he lay behind me like spoons. Telly found the hole I had pre-cut into the rear of my pantyhose and worked me open with a finger or two. I felt his penis touch my ring and I wriggled back so he could slip past my anus, which he did with embarrassing ease. Sure, Telly was smaller than Ron and Tim but I sensed that the rather relentless pounding I'd taken for the past few weeks had loosened up my rectal muscles because he slid all the way in and it didn't even hurt. It actually felt great, and knowing that this was all the penis he had to deal with, or rather I had to deal with, made it fun and relaxing. I massaged my own hard cock through my pantyhose as Telly zipped his cock in and out of my body.

Telly was breathing hard and moved his mouth toward my neck. Tim and Ron had never kissed me or made out with me, so what happened next was downright weird! Telly started to kiss me on the neck as he massaged my shoulders.

"You feel so good. I feel so good inside you", he said.

I craned my neck to try to look at him. "Yeah, it feels really good", I said with a smile. "You feel nice inside me."

It was very dimly lit and almost dead quiet in his apartment except for a radio playing some weird Greek music in the distance, and I was getting fucked in the ass by a perfect stranger while I was wearing eyeliner and pantyhose. Clearly, this had gone beyond simple fantasy indulgence.

"I love your sexy hose you wear", he said. "So soft and silky, like a woman's legs. You are such a sexy man. Feels so nice to feel them on your legs."

Tim and Ron had never talked to me like this and it was...in a word, flattering.

"You look so good", he said. "Your body is so very lovely and sexy, so tight inside you", he said, breathing hard on my neck. The scent of spicy food, liquor, and cologne was a little overpowering, but combined with my silky pantyhose I felt very feminine and willingly submitted to Telly. I rolled over onto my stomach and scrunched up my legs, presenting him with my bottom high in the air. Bearing my weight on my chin, I reached back like an absolute whore and spread my cheeks wide. It felt exhilarating to be so wanton and shameless, and he mounted me easily from above, sliding all the way inside me. His balls were bouncing against my pantyhose and I could feel the thud as his large bag slammed against the thick fabric of the panty section again and again.

"So nice and snug and tight in your body", he said. "You seem so nice, it is so nice to make love to you", he said.

What the fuck?? Make love to me? I had to bite my lip to keep from laughing out loud. "He's Greek, it's his way", I thought to myself, and I decided to play along so he had a nice time.

"Oooh, yeah, baby", I said. "Your big dick inside me, it feels so good", I cooed softly as I slinked back, working and grinding my hips into him. I wish I had a video of this rather amusing scene. It was at that moment that I knew how a woman REALLY feels! I silently laughed to myself, imagining how many times women think up things to say to make a man feel more masculine, complimenting them on their "huge dongs" when in reality they were anything but. So funny, I thought to myself. I continued with encouraging words as Telly fucked my ass with vigorous enthusiasm.

"You feel so good inside me Telly! You're so big and hard and I love it. Feel my legs and my ass. Fill my ass with your hard cock! Fuck me hard!"

His reduced diameter and length translated to an incredibly comfortable session of anal intercourse. I really was enjoying it! He was taking nice deep strokes and pulling out past my ring every few strokes. His size was so manageable; it was great sex and I was bucking and sliding to get his cock rammed harder into my body. Even when he was going at it as hard as he could, Telly didn't have enough volume to stretch me out and it was a nice, relaxing feeling, despite his howling and growling. There was no pain at all which was quite enjoyable, just a well-lubed, fairly small, but hard cock sliding in and out of my body, resulting in pure pleasure for us both. Looking down between my legs at his huge sac was very exciting. His cock was disproportionately smaller than his testicles, but looking at his balls when his dick was buried deep inside me it was easy to imagine a 10 or 12 inch penis sliding all the way inside me. I continued to fantasize that I was getting fucked by a huge dong with Telly's rather slim, short penis inside my body.

Then Telly did something that was truly magnificent. He got above me and, mounting me doggy style, he slowly slid deep inside me and used his legs and hips to pivot his penis vertically inside me. While he did this he slid his hand around my waist and began to use his fingertip to stimulate the head of my penis. His gentle downward surging of his cock began to press on my prostate which felt incredible, and his fingers ever so slightly traced the head of my cock. His rock hard penis repeatedly compressed my prostate and the combination of sensations pulsing and tickling me inside and out were amazing.

"This I think should be good for you now", he said. "I hope it is pleasing to you".

"Oh, my god that is fantastic!", I screamed. "Push it inside me, it feels so fucking good! I'm going to come Telly! I'm coming! Oh my god I'm fucking coming!" Sensations swirled through my body and an incredibly intense orgasm ripped through me.

In a matter of seconds I exploded in a spontaneous, uncontrollable orgasm. I screamed like a maniac as semen jetted out of my cock only to be trapped by my sweaty pantyhose. Pulse after pulse of come filled the nylon mesh as Telly's rock hard penis gently nudged me deeper and deeper into an amazing full-body orgasm. What began as mediocre sex, nearing what almost became a charity fuck, quickly turned the corner and became an outstanding sexual experience. Now my screams and words were genuine.

"Oh, baby, it feels so fucking good!! It's feels so fucking good!", I yelled. "Oh, you're so deep inside me, and your fingers on my cock feels so awesome, my god that is fantastic!"

Telly quickly began to experience his own climax. He yelled and then quickly pulled out of my body and I could hear him fumbling with his condom. As I turned my head I could see him jacking his cock and within seconds he erupted with a huge load of come all over my back and ass. As he continued to pump his cock I could feel warm blobs of semen dripping down onto my ass cheeks and upper thigh through my pantyhose, a sensation I loved. I felt like a cheap whore getting splayed and sprayed, fucked in the ass and then accepting a huge load of come all over my body, staining my pantyhose with semen, sweat and anal lube.

After he and I calmed down and separated, I said, "I loved you coming on me. It felt great! No one has ever done that to me and I really liked it".

"Yes, this was so very nice. I am glad you liked the ending. And I love you in your pantyhose, so sexy!" He smiled and went into the bathroom.

While he was in the bathroom I said, "I guess it's especially nice when men who wear them let you fuck them up the ass!"

I could hear him laugh in the bathroom, "Yes, that is especially nice certainly!"

Telly returned to the room and said, "Your turn if you would like to when you are ready of course."

"Yeah, that would be great", I said. Amazingly, in a matter of minutes, I was hard again.

I rolled him onto his stomach, lubed him up and began to spread his ass with my thick, greasy fingers. He was not as tight as Ron but I sensed that there would be plenty of friction for my rigid penis. After I had eased him open a little, my cock head replaced my fingers, pushing at his hole. Telly moaned really, really loud as the head slipped inside his body. I gave him a few seconds to get used to me, then slid a few inches deeper.

"Oh, it feels so very good", he moaned. "Push all the way, but please go slowly. It has been a while for me."

I gently nudged my penis inside my new friend, coming to rest deep in his ass, my balls trapped by my pantyhose, which was a wonderful feeling. Telly was hesitant and tight and nervous and it took several minutes for him to relax enough for me to fully penetrate him in comfort. I fucked him doggy for a few minutes and then he decided to get on his back, which made it much better for both of us. He loved it in this position and I gave him a nice, solid reaming for a good 15 minutes, his legs intermittently draped over my shoulders or bent at the knees. He was lubed and spread and he was loving the anal treatment. He had a really nice set of balls for a mediocre sized cock. His sac was huge and his two nuts were hemmed in tight by a thick, olive-skinned leathery bag sprinkled with soft, dark curls of hair.

"Fucking me so nice", he whispered, looking up at me. "Making love to me so very nice and deep, my friend. So good, so nice and slow and deep, oh it feels wonderful. You are so sexy and so good. You know how to fuck me so nice. You are so gentle with me even though you are a wide one. Feels good but please not too hard still."