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My education continues after my virginity was lost
By
juanmoretime1

My education continues after my virginity was lost

My girlfriend tells me a story and introduces me to anal her way. Part1
I met Madeline during my senior year of college and detailed our first time in my last story. The way we met was due to the radio show I was producer director of at the school and Madeline was my Arts reporter. This was the original format show which spawned Evening Magazine on television. This meant we spent many dates going to the theater and concerts around town. After the first time we made love, we became exceptionally close and I moved in after we graduated that year in June.

We lived in an apartment in Boston with another roommate. We were making love constantly and, at 6’4” (she was 5’8”) sleeping one single bed made for extreme closeness and many mornings awakening and having great sex. The bedrooms were separated by the living room, so the moans and cries of lovemaking were muted.

Just prior to my moving in, Madeline went to NYC to visit an old boyfriend who was supposed to have gone gay. I thought nothing of it at the time and she was gone for a three day weekend. When she came back Monday afternoon, I picked her up at South Station off the train. When she saw me she bolted to me and gave me a hug that almost crushed my ribs followed by a passionate kiss.

“Wow,” I exclaimed, “that must have been some weekend.”

“Yes, but I missed you terribly. I can’t wait to get back to the apartment and shower and tell you all about the trip,” she said.

We went home and she went into the bathroom for her shower while I made some chicken stir fry and rice for our supper. I opened a bottle of Pouilly Fuisse and poured a couple of glasses just as she came out of the bathroom. I handed her the wine and we sat down with our plates of food in the windowed alcove looking over the street down below (don’t get excited – we were on the second floor.

“So tell me what happened,” I said.

“I arrived Saturday around 11 at Penn Station and John met me with his friend Brad. We went to the Stage Deli for pastrami sandwiches with hot deli mustard, swiss cheese, and saurkraut. They were awesome. They were so big I took half of it to the apartment to eat later. We sat for a while and had some wine and John took out some incredible pot and we rolled a joint and got high. It was incredible. We talked and talked. Then we got going to the theater and saw South Pacific. Boy, the sets and costumes were fantastic! ”

“Sounds like a good time,” I said.

“Yes it was. But it got a little awkward when we got back to the apartment.”

“Oh, why is that?” I asked.

“When we got back, we smoked and drank some more and got really toasted. Then Brad went to the bathroom and, well,” Madeline looked down at the floor, “John kissed me.”

“Really?” I said, not knowing whether to be jealous after all it was her ex and she is living with me. “was that all?”

“Well I was so high, and it felt so good to kiss him. While we were kissing, Brad came back and he came around my back and hugged me from behind and put his head on my shoulder, kissing my neck and sending shivers down my spine. When I reached my arm back I discovered he was nude! I stopped kissing John and turned around inadvertently hitting Brad’s huge and hard cock when I did with my hand.”

“What did you do?” I asked, getting excited and hard despite my trepidation and fears.

“I told them I was going with you and it wasn’t right to step out on you like that. I was surprised. At that point, John hugged me from behind and kissed my neck saying that it was all right and to think of it as a vacation. It was then I felt John’s hard cock on my thigh and I began to feel my cunt flush with wet excitement and realized he had stripped naked too. Here I was, surrounded by hard naked male flesh. I was leaning back into John’s embrace with my eyes closed when I felt Brad begin to lift my shirt up over my head and take it off. John leaned back a bit and undid my bra, sliding it off while Brad then depantsed me leaving me in my nylon pantyhose, stained with the leaks from my now very juicy pussy. My nipples were hard and erect. Brad leaned down and grabbed my left breasts with his hand while he affixed his mouth to my right nipple and sucked hard. I moaned and lost myself to pleasure.

A tremor gripped me and I experienced a huge sensual flush. It wasn’t a full orgasm but it sure felt good! I grabbed Brad and pulled our nakedness together and we kissed deeply. I am sorry Bill, I was just overcome with sexual emotion. John reached down and poked a hole in my hose, and ripped a slit between my legs exposing my ass and cunt to their whim. He began massaging my cunt rubbing back to my asshole. It felt so good.”

At this point there came a rattle at the front door as our roommates came home. We had leaned in and were closer at that point, and I was having a hard time with a raging erection at the description I was hearing. I was totally conflicted but very excited by the story and where it had gone. We backed into our seats as they came around the corner.

“I will tell you the rest later. I don’t want Christine or Andy to know what happened…. Oh Hi guys!” Madeline said as the roommates walked in.

The rest of the night related to the theater and museums she visited in conversation with the roommates and we tabled the discussion of her sexual encounter – her first threesome it appeared.

Friday, we awoke and decided to take the weekend down in Wellfleet on Cape Cod. It is at the elbow of Cape Cod and has magnificent beaches and some of the warmest sea water in New England. We bucked the traffic and ended up at a small motel on the beach. We went and ate some great steamed and fried clams at a local seafood shanty restaurant and returned to our rooms.

Once we got in and settled, I grabbed her and we kissed deeply and held each other for some time. We were wearing t-shirts and jeans which we shucked in favor of being naked. I was half hard and her nipples were excited and standing, awaiting my mouth. We smoked a joint and then it started.

“Madeline, can you continue the story we interrupted of you sexual encounter with John and Brad?”

“Okay, but let’s lie down on the bed and you can rub me while I tell you. Here, I brought this massage oil to use.” She handed me a bottle of raspberry flavored massage oil.

Madeline lay on her stomach and put her head down on her folded arms. She rolled a bit and spread her legs enough that her cunt was exposed. I got on the bed and straddled her with my ass resting between her legs and my half erect cock within sight of it’s objective between her thighs. I poured a bit of oil on her shoulders and down her spine in a thin line. I began to spread it around with my hands, warming to the task.

“Okay. Let’s have the rest and spare no details!” I continued my massage of her back, slowly dropping lower.

“I think we were in the initial embrace when I left the story. Naked hot flesh surrounded me and John was running his hands down my sides as he kissed my neck. His hands wound around and one began rubbing my wet pussy while the other grabbed Brad’s erect cock, masturbating it. Brad was sucking on my breasts and rubbing the other with his hand. I was feeling so hot. My mind was blank with sexual emotion and I was lost inside the feelings. I urged them to go to the bedroom and we decoupled and wandered there, John rubbing my ass and Brad grabbing his own cock as we went.”

[I was massaging her back and sliding my hands around rubbing and pressing her back and the sides of her breasts at this point. My cock was getting hard and was feeling the heat from her now wet pussy…]

I lay down on the bed and looked back up at them. They were next to each other looking at me, both erect and ready. They looked at each other and then lay on either side of me. They went up on their elbows and, leaning over me, began to kiss each other while their hands wandered my body. John’s free hand went down and began rubbing my wet pussy, while Brad’s hand rubbed my breasts and squeezed the nipples. I lay between them in amazement having never seen two men sensuously kiss. They broke and Brad went straight to my erect nipples, sucking them right in while John scooted down and began to lick me. Ooh was that fine! I was enthralled with erotic feeling!”

[Madeline adjusted her legs opening a bit causing me to interrupt my massage and move forward, my foreskin sheathed hard cockhead rubbing her slit and wetness. I continued my rubbing, hands moving to her lower back.]

“John began sticking his fingers in me while Brad moved in and began kissing me. One at a time, a finger entered me until three were engaged in my pussy slowly rubbing me inside. His thumb was rotating around my anus, something no one had done before. It felt odd but, in combination with his fingers in my pussy, I ended up moving my ass and, with the pussy juice lubrication, he ended up penetrating me in the ass with his thumb. It felt great as he started pumping both holes while he licked my clit sending sparks to my brain and driving me towards a tremendous orgasm. When it hit my body vibrated as Brad broke our kiss, still manipulating my breasts and nipples. My head moved side to side while I moaned through an incredible climax. We stopped for a few minutes to let me catch my breath.”

[By now I was hard as a rock listening to and imagining the event as described to me. I slid forward and the head of my cock entered her and I sat still, luxuriating in the feeling of her wet heat.]

“After this I was a bit wrung out and needed a brief break. We smoked another joint and then Brad slid over me and on top of John and they began seriously making out, their hard cocks together between them. John was on the bottom and I noticed Brad’s hand go down and begin to play with John’s anus. They broke away from each other and looked at me and asked if they had ever seen two men fuck and would I mind if they went ahead and showed me. I was horny, stoned, and curious so I agreed to see it. Brad reached over to the end table beside the bed and grabbed the Astroglide and handed it to me. He requested I oil them both up. I was into this that I agreed.

John rolled onto all fours, doggie style, and exposed his ass to me. I squirted some of the lube on his anus and rubbed it in. Then I did something that amazed me and slipped two fingers into his anus and pushed them in and out, lubing and stretching. Brad came before me and wagged his hard cock in front of my face and I took him in my mouth and began to suck him while I plunged my fingers into John’s ass. It was so exciting I couldn’t believe it. Ohhhh Bill - you.”

[At this point I had slid my cock into her directly and all the way. In my excitement I abandoned my massage of her back and began to fuck her.]

“Bill, wait. There is more. I don’t want to fuck you yet. You will see why in a minute.”

I stopped, “you sure?”

“Believe me this will be better.” She said. “Here let me roll over and you can play with me while I finish the tale. Please play with me while I tell you the rest of the tale.”

I smiled, “If you insist.”

Madeline rolled onto her back and we kissed sensuously for a few minutes. I then lay beside her on my side and fondled her between her legs while I moved my mouth and tongue to her erect nipple on the right side.

“After I was sucking Brad and thrusting my two fingers into John’s ass while he was in a doggie position for a few minutes, John’s ass had loosened and was moving back and forth in tandem with my fingers. Brad’s hard cock was coated in my saliva and working in and out when he pulled back and made to go around me to a position behind John. I pulled my hand away and watched while Brad slowly slid his cock into John’s ass. John’s cock was hard and I went underneath and began to suck him while watching Brad fuck his ass from below. Brad was really getting into it, plunging faster and faster and causing John to move in my mouth as well. I was so excited I began to rub my pussy, the juices bubbling from within during my manipulation. After some minutes, Brad started to say he was going to cum. At that moment John groaned and erupted huge amounts of semen which I was trying to swallow. With John’s ass clutching his cock as he spasmed, Brad groaned and came as well. Copious amounts of cum started to come out of John’s ass and slide down his legs. I got so excited with rubbing my clit that I came as well. It was incredible.”

At this point, I was hard as heck and randy as hell. I moved to mount Madeline and she pushed me back.

“Bill, wait there is more. Not trying to tease you, as you will see. So let me do this,” she said.

With that she pushed me on my back, peeled back my foreskin, and began to slowly suck my hard cock deep in her mouth. At the same time, she brought out a bottle of anal lube and squirted some on her fingers, nudged my legs apart, and she proceeded to slide into my ass while she furiously wound her tongue around my cockhead. She started with the penetration of one finger. It had been years since my ass had been played with and it felt good. One by one she added the other two fingers drenched in lube so I felt the slippery stuffed sensation in my ass while she sucked me. I was feeling incredible sensations as I had never been treated to this before.

Just as I was getting towards the top of excitement, suddenly the friction and plunging in my ass got to me and I erupted in flowing hot semen into Madeline’s mouth. A veritable explosion! I felt my ass muscles grip her fingers and she stopped and quickly removed them causing another spurt. Wow. What an orgasm.

The rest of the story comes in Part 2.

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